Jerry Reinsdorf

January 29, 1981, was one of the most impactful days in White Sox history.

That was the day Jerry Reinsdorf assumed control of the club, getting a 14-to-0 vote from American League owners at the O’Hare Hilton. Reinsdorf would go on to become the longest-tenured owner in the major leagues. At age 88 in 2024, he was also the oldest owner.

The White Sox have two owners in the Hall of Fame. Charles Comiskey (Commie, The Old Roman) ran the club from 1900 until his death on October 26, 1931. Bill Veeck, whose Hall of Fame plaque identifies him as “A Champion of the Little Guy,” had two stints owning the club. Veeck ran the team for the 1959, 1960, and part of the 1961 seasons. Then he owned the White Sox from 1976 through 1980 before selling to Reinsdorf’s group. Reinsdorf’s tenure now exceeds that of both Hall of Famers – put together.

In retrospect, the White Sox sale of $20 million in 1981 appears to be a bargain. The Philadelphia Phillies sold later in the same year for $30 million.1 The Twins went for $44 million in 1984.2

To be clear, Reinsdorf is not the sole owner. The White Sox Media Guide phrases it a particular way. He heads a limited partnership and is the “controlling” owner.3

While details are not public, Forbes has reported that Reinsdorf owns 19 percent of the White Sox.4

A Phil Rosenthal story says there were as many as “25 to 30” limited partners at the start, but the key executives were Reinsdorf and Eddie Einhorn.5 Einhorn and Reinsdorf had met in law school. Einhorn was a successful broadcasting pioneer. Reinsdorf was a successful tax attorney. Einhorn died on February 24, 2016.

Reinsdorf had long dreamed of becoming a major-league owner. He had been a passionate childhood fan of the Brooklyn Dodgers since age 9. His favorite player was Pee Wee Reese, with a soft spot also for Duke Snider, who once lived on his block. Reinsdorf had attended, he said, the first game where Jackie Robinson suited up as a Dodger in Brooklyn.

As an adult, Reinsdorf answered an ad in the Wall Street Journal looking for potential baseball investors, and he was part of a group trying to buy first the San Francisco Giants, then the Cleveland Indians and finally the New York Mets.

Then it came to him. He would become an active leader of an ownership group.

He reckoned his chances of achieving that dream as “Infinity to 1.”6

“I’ve always looked at the ownership of a baseball franchise as a public trust, maybe even a charitable thing,” Reinsdorf said. “I’m serious about that. I never did forgive Walter O’Malley for moving the Dodgers from Brooklyn to Los Angeles.”7 Reinsdorf once said he rooted against the transplanted Dodgers. Yet calling himself a practical businessman, Reinsdorf has the White Sox share a spring-training facility with the Los Angeles Dodgers at Camelback Ranch in Glendale, Arizona.

Born February 25, 1936, Reinsdorf is the son of Max and Marion Reinsdorf. His father was a sewing machine mechanic and salesman. Jerry grew up in a middle-class Brooklyn family, which lived in an apartment. He slept on a rollaway cot in the hallway.

He was educated at George Washington University and earned his law degree at Northwestern. Northwestern changed him from a New Yorker to a Chicagoan. He worked as a lawyer for the Internal Revenue Service and also became a certified public accountant, a registered mortgage underwriter, a certified review appraiser, and a real estate securities specialist.8

Reinsdorf was a co-founder of one of the nation’s first businesses that specialized in real estate partnerships. He sold the firm to American Express for $102 million, leaving the firm in 1987.

The success of the Reinsdorf-led bid to buy the club was not a given. There were other suitors, notably Edward J. DeBartolo Sr. DeBartolo was the early front-runner, but there were concerns. As an Ohioan, he would have been an absentee owner. There was also a worry about his links to horse racing, which by 2024 seemed completely out of date given baseball’s on-air promotion about betting parlays. So the Reinsdorf group prevailed.

The Reinsdorf era started dramatically and well. Reinsdorf and Einhorn said they were not interested in building a team with free agents.9 But in March 1981 the White Sox added free-agent catcher and future Hall of Famer Carlton Fisk and purchased slugger Greg Luzinski from the Phillies. But Reinsdorf also expanded the farm system.10

In 1979 the White Sox had a meager three farm teams, in Des Moines, Knoxville, and Appleton. By 1982 the minor-league roster had expanded to include the Triple-A Edmonton Trappers, Double-A Glens Falls White Sox, the Single-A Niagara Falls Sox, and the Rookie-level Gulf Coast Sox. Management continued to build the farm system for the next decade. By 1995 Chicago had seven minor-league affiliates: Triple-A Nashville; Double-A Birmingham; Advanced-A Prince William; Single-A Hickory and South Bend; Rookie League teams in the Gulf Coast and Appalachian leagues; and a Foreign Rookie team shared with the Baltimore Orioles in the Dominican Summer League.

For immediate help, “Carlton Fisk just fell into our laps,” Reinsdorf said. “Boston lost him on a technicality, and we thought we had a great opportunity to get a great player. The White Sox hadn’t had a great player in a long time.”11

But while the team was about to turn north, its media presence headed south. The year 1982 marked the beginning of SportsVision, an Eddie Einhorn project.

Under the slogan of “Chicago’s Winners on Cable,” the games of the White Sox, Bulls, Blackhawks, and Chicago Sting soccer team would be beamed to your television screen if you purchased a $50 converter box. Almost immediately, cheaper knock-off boxes appeared. The goal was 50,000 customers. Promoters never came close to that.

The choice between free televised Cubs and White Sox games that required a special price and effort was not a good one for the South Siders. Broadcaster Harry Caray described the White Sox on television as a “best kept secret.”

SportsVision was dead before the end of the decade, but not before it had widened the public gap in baseball interests between the North and the South Sides.12

In 1983 White Sox pitchers LaMarr Hoyt (24-10, Cy Young Award winner) and Richard Dotson (22-7) both had the best years of their careers. Ron Kittle was Rookie of the Year with 35 homers and 100 RBIs. The White Sox were 59-26 in the second half and won the Western Division title by 20 games. Texas Rangers manager Doug Rader accused the White Sox of “Winning Ugly.” The name stuck. To this day, the 1983 season evokes nostalgia among fans and those throwback uniforms remain popular.

Reinsdorf would later say that while the 2005 World Series championship was the most satisfying thing, 1983 was “the most fun I ever had.13

Starting a pattern, the White Sox fell short in the postseason, losing to the Baltimore Orioles in the AL Championship Series. The year also proved to be a single high peak, followed by a valley. Reinsdorf called the balance of the 1980s “the outhouse.”14

A crisis came in 1986, broadcaster Ken Harrelson, who had been openly critical on the air of general manager Roland Hemond, was elevated from microphone to management. Harrelson fired future Hall of Fame manager Tony La Russa. He himself stepped down with a week to go in the season. Reinsdorf called the dismissal of La Russa “the dumbest mistake of my life.”15

That year Reinsdorf announced plans to build a new ballpark in the suburbs. Before the 1998 arrival of the expansion Devil Rays, Tampa was ready to host the White Sox.

“It was very hard to get our new ballpark built, but it had to be done because the old ballpark was going to fall down.” Reinsdorf said.16 “It was truly at the end of its useful life, and it was well beyond the end of its economic life, because with the salaries escalating the way they had, you had to have new sources of revenue from a ballpark and you couldn’t find them in the old Comiskey Park. Also physically it wasn’t going to last much longer.”

On June 30, 1988, time stood still as the Illinois legislature raced a deadline to approve the funding for a new White Sox stadium, which was first named Comiskey, then US Cellular, and later Guaranteed Rate Field.

“Now we stay. This thing was dead and one man did it,” Reinsdorf said of the stadium vote.17 He meant Illinois Governor James Thompson, who lobbied hard on behalf of the White Sox. In 2022 the team installed a bust of Thompson outside Gate 4.

Much of the lease agreement held the Illinois Sports Facility Authority to a strict deadline to get the new ballpark open and then specified responsibility for repairs. Clearly, the deterioration that occurred in Old Comiskey would not be repeated. Today, the ballpark is no longer “new,” but it appears well maintained.

The White Sox are tenants. They do not own the ballpark.

The Authority gets a share of ticket sales. Since 2001 the Sports Facility Authority begins getting paid once home attendance hits 1.5 million. The White Sox have hit that number every year since, with the exception of the Covid year in 2020 (when there was no attendance) and the dismal 2024 season. Increased attendance not only benefits the White Sox, but also the Authority.

The Authority is responsible for all property taxes. The lease makes that clear. The White Sox get the revenue and have control of all concessions and souvenirs. The team also has control of and revenue from all signs. The Authority gets 35 percent of all “Media Fees” above $10 million.

It was a detailed lease, setting aside specific tickets and a suite for the Authority’s use and even specifying the material for the infield tarp used when it rains.18

The team returned to relevance in the early 1990s. Old Comiskey closed. The new ballpark opened in 1991. Three straight years above .500 were followed by a Western Division title in 1993. It was the birth of “Good Guys Wear Black,” which started as an advertising promotional slogan.

The 1993 team was fueled by home-grown players signed and developed by the White Sox: Frank Thomas (MVP, 41 homers, 128 RBIs); Robin Ventura (22, 94); Jack McDowell (Cy Young Award, 22 wins) and Alex Fernandez (18 wins). As in 1983, the White Sox exited the playoffs in the first round, this time losing to the Blue Jays.

Reinsdorf bought the NBA’s Chicago Bulls in 1985 and hired Jerry Krause as general manager. Krause inherited Michael Jordan, but built the team of Scottie Pippen, Bill Cartwright, and Horace Grant around him. It was the first of two three-peats for the Bulls in the NBA. In 2016, Reinsdorf was elected to the Naismith Memorial Basketball Hall of Fame as a contributor.

When Jordan temporarily retired in the middle of these title runs, Reinsdorf accommodated his wish to try the sport of baseball.

August 11, 1994, was another watershed day in the history of the White Sox, in all of major-league baseball and in the way Jerry Reinsdorf would be regarded.

That was the last day major-league baseball was played that year after players went on strike. When the schedule stopped, the White Sox were in first place in the new American League Central Division by a game. The short season wasted what was the best year in Frank Thomas’s career: his top season for batting average (.353) and slugging (.729), with 38 homers and 101 RBIs. Thomas was a near-unanimous MVP, getting 24 of 28 first-place votes. It was his second straight MVP, an achievement ironically celebrated with a bobblehead during the disastrous 2024 season.

Major-league baseball teams had drawn an average of 30,965 fans a game in 1993. That dropped by more than 5,000 per game in 1995 after the strike. It would take until 2006 to reach the pre-strike per-game average. Overall attendance was juiced by the addition of Arizona and Tampa Bay in 1998. Some fans stayed away – for years.

If the fans were losers, so was Reinsdorf. The media portrayed him as “the influential anti-union hardliner.”19 Steve Wulf called him “the hardest of the hard-line owners warring with the players’ union.”20 Reinsdorf said he was a “dove” on the issue until the strike began, then he became a “hawk.”21

While Reinsdorf was described as a “back-room puppeteer” powerbroker, Sports Business Journal said that more often Reinsdorf zigged while the other owners zagged.22

During the strike, Reinsdorf advocated that the owners introduce their own labor rules. The counter-argument was to wait and use the threat as a warning. Reinsdorf’s proposal lost in committee, 18 to 1.

“I had it right, but nobody went along with me. So we had to fold our tent,” Reinsdorf said. “I know that I got blamed for the strike, but the only one to blame for the strike, in my opinion, was Don Fehr. He’s the guy who called the strike.”23

Forgotten by many fans today, Donald Fehr was the executive director of the Major League Baseball Players Association from 1983 to 2009. For Fehr and the players, the key issue was avoiding a salary cap, but the new contract would establish a “luxury tax,” which the highest-spending teams would have to pay.24

Back on the field, in the late ’90s through 2000, the White Sox added thump. Ray Durham joined in 1995 (106 homers with the White Sox, career of 192). Magglio Ordóñez came in 1997 (187 homers with White Sox in a career total of 294). Former Dodger and Red Paul Konerko started with Chicago in the same year (439 homers lifetime, all but seven with the White Sox). Carlos Lee arrived in 1999 (152 home runs with the White Sox, career of 358). José Valentin started in 2000 (136 with the White Sox in a career of 249).

The most controversial add was Albert Belle, he of the corked bat, “batgate.” Reinsdorf signed Belle for an estimated $52.5 million for five years, making the oft-suspended hitter the highest paid player in the major leagues.25 Reinsdorf had often preached fiscal responsibility to other owners, but now seemed to have not listened to himself.

“Any owner who breaks the market like this with the industry in trouble, it makes you scratch your head,” said John Hart, the general manager of the Cleveland Indians.

Reinsdorf countered. “In the current climate, you have to pay to win. Look at the World Series: the No. 1 payroll vs. the No. 2.”

Reinsdorf declared that if the Chicago fans could accept Dennis Rodman, “the fellow with the pink hair,” they would accept Belle.26

Belle had two good seasons for the White Sox, setting a team record with 49 homers and 152 RBIs in 1998. But a clause in his contract allowed him to try to renegotiate if he was not among the three-highest paid players in the game. Reinsdorf said no. Belle’s stay was short.

A breakthrough came in 2000. The White Sox had six players with 17 home runs or more en route to a team record of 216. They won the Central Division, but had another quick playoff exit, swept in three games by the Seattle Mariners. Once more, it was one and done.

By 2005 the White Sox had a new manager in Ozzie Guillén, a new fight song in Journey’s “Don’t Stop Believin’” and a new philosophy, discarding power for speed, defense, and pitching. Every acquisition seemed to work.

Orlando “El Duque” Hernandez, A.J. Pierzinski, Jermaine Dye, and Tadahito Iguchi would arrive as free agents. The White Sox traded for Scott Podsednik and Freddy García. Bobby Jenks was plucked off the waiver pile. All would play vital roles in a 99-victory regular season and an 11-1 roll through the postseason.

The acquisition of Podsednik was a clear signal of a changing team. Essentially, the White Sox swapped outfielders with the Brewers. Gone was Carlos Lee, who would hit 32 homers for the Brewers in 2005. Podsednik would steal 59 bases in 2005. Power out, speed in. Podsednik did not hit a home run in the 2005 regular season, but did win a World Series game with a walk-off homer.

But there were two other aspects of the trade. Pitcher Luis Vizcaino joined Chicago. He went 6-5 for the season, making 65 appearances. There was a significant cash benefit for Chicago, too. Lee’s leaving took a $6.5 million contract off the books, while Podsednik was making $700,000.

The new team speed and the ability to play for one run when needed were key factors in a world championship.

“It was only afterward that I realized the impact that winning the World Series had on our community. You could have gone to any cemetery in the Chicago area and found graves decorated in White Sox paraphernalia,” Reinsdorf said.27

At the victory celebration, Reinsdorf was “stunned” when first baseman Paul Konerko handed him the ball that was the last out of the World Series.28 The year before, the Red Sox ended up with a lawsuit to recover their last ball from their first baseman.

“When Paul handed me that ball, it just choked me up. It was a tremendous feeling,” Reinsdorf said.29 It even got Jerry in a bit of trouble with his wife when he said it was most emotional moment of his life. Wife Martyl reminded him of their marriage and the birth of their children.

The 2006 season marked a familiar regression. Broadcaster Harrelson kept telling the audience that the team would win 90 games and be fine. The White Sox did indeed win 90, but that was only good for third place. The top of the mountain was again followed by a valley.

There was a rebound in 2008. A coin flip gave the White Sox the home field in a one-game tiebreaker against the Twins for the Central Division title. Jim Thome won the “blackout” game (so named because the fans were encouraged to wear black shirts) in dramatic fashion with a solo shot for the game’s only run. The playoff series against the Rays, though, was another quick exit.

It took another dozen years for the White Sox to get back to the postseason. Bopper Adam Dunn arrived in 2011 for four years that would see 106 homers and 720 strikeouts. All or nothing. From 2013 to 2019, there were seven straight years when the team finished under .500.

Mired in the middle, Reinsdorf gave the signal to team architects Kenny Williams and Rick Hahn to rebuild the team. That meant trading some quality veterans for prospects.

“We always say we want to win multiple titles,” Reinsdorf said. “The real plan is we want to be competitive year after year. It’s very hard to win one title, let alone multiple titles. I just want us to be playing meaningful games every October. … (Deciding to rebuild) was an easy decision, because (if) we didn’t make that decision, we were going to be caught in mediocrity, and that’s no fun.”30

There were three key trades. Star pitcher Chris Sale was sent to the Red Sox for Yoan Moncada and Michael Kopech. Pitcher Jose Quintana was dealt to the Cubs for Eloy Jiménez and Dylan Cease. Outfielder Adam Eaton traveled to the Nationals in return for Lucas Giolito, Reynaldo López, and Dane Dunning.

At first it seemed to work. The 2020 season was abridged by covid, but José Abreu was an RBI machine, knocking in 60 runs in 60 games and winning the MVP Award. Yet while it was back to the playoffs, it was another fast exit, courtesy of Oakland.

That was followed by the speedy exit of manager Rich Renteria, who seemed to have performed his designated role of teaching the team’s younger players. Renteria’s departure prompted a stunner – the return of Tony La Russa. There were two immediate media and fan reactions, both negative.

La Russa had last actively managed in the 2012 All Star Game after winning the 2011 World Series with the Cardinals. He had been out of baseball for three years, then successively served as chief baseball officer for the Diamondbacks, adviser for the Diamondbacks, and assistant to the general manager for the Red Sox.

The change seemed to cement the idea that Reinsdorf was still actively running the team. And La Russa was seen as out of touch with today’s players, out of touch with the modern rules, and out of touch with baseball analytics.

Reinsdorf was having none of it.

“As everyone in baseball is well aware, I have always respected Tony and am proud to have maintained a great friendship with him over the decades in the game. But his hiring is not based on friendship or on what happened years ago, but on the fact that we have the opportunity to have one of the greatest managers in the game’s history in our dugout as a time when we believe our team is poised for great accomplishments.”31

At 76, La Russa was the oldest manager in baseball. He already had a plaque in Cooperstown. Yet it did seem to work: The White Sox won 93 games in 2021 and won the Central Division by 13 games – the first time they had back-to-back postseason teams. But once again, the White Sox were out in the first round, losing to Houston in four games.

In 2021 the White Sox won the nationally televised Field of Dreams game in Dyersville, Iowa, with a sensational bottom-of-the-ninth homer from Tim Anderson. The bat-flipping Anderson was the inspiration for another memorable slogan, “Change the Game.”

The next year, 2022, started a steep decline. The playoffs were expanded, but the team slumped to 81-81 and missed them entirely. On the advice of his cardiologist, La Russa stepped down as August ended.

Pedro Grifol was hired as the manager for 2023. The team did not respond well. Losing 101 games, the White Sox had their worst season since 1970, when they lost 106. Toward the end of the season, Reinsdorf fired both Kenny Williams and Rick Hahn, the two men responsible for the roster. It wasn’t an easy decision for Reinsdorf.

“One alternative was to do nothing. Another was to keep Kenny and let Rick go, and another was to keep Rick and let Kenny go. And I came to the conclusion that it’d be better to let them both go and have a fresh start,” Reinsdorf said. “A change killed me because it wouldn’t have been any harder for me to fire my son, Michael, than it was to fire Kenny because Kenny was my son and is still my son.”32

While the firings were generally expected, the replacement was a disappointment to many fans and the media because Reinsdorf simply elevated Chris Getz, the White Sox assistant general manager in charge of minor-league operations. Criticism ran along two lines. Should a more thorough search have been done? Had the White Sox minor league operation been all that great anyway?

Speed, Reinsdorf said, was of the essence. He wanted a quick turnaround. There was no widespread job search, there were no interviews of anyone outside the organization.

“It became clear to me that (Getz) would be one of the major candidates, alongside these other candidates. And then I started thinking of the speed I owe the fans, I realized that if you bring in somebody from the outside, it’s gonna take him a year, he’s gonna have to evaluate everybody in the organization. So you’ll lose a year.”33

The hiring of Getz from inside the organization was the latest in a long-term trend of loyalty, for better or worse, for current and former employees. Hawk Harrelson is in the broadcast booth, gets promoted to run the team and fails there. He returns to telecasts. Ozzie Guillén departs as a player, returns as a manager, departs again, and returns again as a television analyst. Frank Thomas leaves as a player and returns as an analyst, too. Robin Ventura also leaves Chicago and comes back as a manager.

Institutional loyalty is a White Sox value for Reinsdorf. “Peter Gammons once said to me, ‘Is there anybody here who answers the telephone who hasn’t been here for 20 years?’”34

Ozzie Guillén, who has returned to the White Sox fold twice after departing, once called Reinsdorf “the greatest man I ever met, not because he’s my boss. Because he’s a straight man who will not lie to you.”

“A lot of people should know Jerry the way I know him,” Guillén continued. “Jerry means well for everybody, especially in this city. Jerry is treated so badly in this city. I think Jerry should be more loved, more respected.”35

The time gained by hiring Getz, though, was one of agony. The fade continued and accelerated.

In 2005 every signing and trade seemed to go right. Now everything went wrong.

In Yoan Moncada’s first eight years with the White Sox, he topped 130 games played only three times. His best year came in 2019, when he hit .315 with 25 homers. Moncada hit 93 homers for the White Sox through the end of the 2024 season, but making contact was a problem. He had five seasons of 100 or more strikeouts, topped by a league-leading 217 whiffs in 2018.

Eloy Jimenez played six years in Chicago before being dispatched in a trade to Baltimore. In no season did he top 130 games played. His best year also came in 2019 with 31 home runs.

Luis Robert, developed by the White Sox, had only one season in his first five where he reached 130 games played. In 2023 he hit 38 home runs. Tim Anderson, also a White Sox farmhand: batting champion at 26, All-Star at 28 and done as an effective player at 30.

Yasmani Grandal, signed in free agency to handle the catching duties, had only one year, out of four, when he played 100 or more games. In 2021 he hit 23 homers, more than his other three South Side years combined. Free agent Andrew Benintendi hit .273 for the Red Sox and .294 for the Royals, but less than .240 for Chicago in 2024. Benintendi’s five-year, $75 million contract had been the richest in White Sox history.

Meanwhile, pitchers Chris Sale and Reynaldo López, both traded away, were All-Stars. Dylan Cease, Jose Quintana, and Michael Kopech, also traded from Chicago, were effective, as was Carlos Rodón. It was as if every estimate of talent had been wrong, and every possible injury had occurred.

Picking the worst possible timing, the White Sox announced plans for the new ballpark in February 2024. Located along the river between the South Loop and Chinatown, it would be part of a development called The 78. The ballpark alone would cost $1.1 billion, funded by a hotel tax, and there would be $900 million more needed in infrastructure.36

The new ballpark would be blended better into its surrounding community than Comiskey-Cellular-Guaranteed Rate. Parking would shrink. Skyline views would improve. More and better restaurants would arrive. Sodfather Roger Bossard, the White Sox groundkeeper, has laid out a baseball diamond on The 78 site to give the public and the decision-makers a visual.

Guaranteed Rate is the eighth oldest ballpark in the majors. The three oldest, Fenway Park, Wrigley Field, and Dodger Stadium, are unlikely to be replaced. Only two ballparks, for the Braves in 2017 and the Rangers in 2020, have been built since 2012.

The 2023 season was marred by a shooting inside Guaranteed Rate Field, during an August 25 blowout loss to the As. Two women were injured; Neither injury was life-threatening.37

The White Sox drew some criticism for continuing to play the game, but reports indicated that that was a police decision to avoid panic. An ESPN reporter said the shot or shots were accidental and from a gun that was likely “snuck in.” The police said that was the most likely scenario. Meanwhile the White Sox would not rule out the idea that the rounds came from outside the ballpark.

A lawsuit was filed against the White Sox and the Illinois Sports Facility Association. The entire incident seemed to reinforce the worst fears about the ballpark’s location.

Yet fans have shown a willingness to attend. Fourteen times in the Reinsdorf years, attendance has topped 2 million. Most of those seemed to coincide with better teams, led by the 2,957,414 in the post-World Series year of 2006.

And today, as you walk inside the ballpark, the concourses are wide, with activities and lots of food choices. The audio and video systems are sharp. Colorful murals display team history. Statues of White Sox greats stand. Guaranteed Rate does not look or feel run-down.

Talking to Crain’s Chicago Business, Reinsdorf left little doubt that the White Sox would depart without a new ballpark. The current lease runs through 2029. He told Crain’s that when he’s gone, his heirs would be obligated to do what’s best for the other investors. “The big money” in the White Sox comes from out of town, he said.38

Son Michael, the Bulls’ president, has been advised to hold onto that franchise, though.

The veiled threat to move the White Sox feels creepily like the pressure that built the current ballpark. As Yogi Berra might have said, “It’s déjà vu all over again.” Nashville is mentioned as the most likely suitor, and Reinsdorf did meet with Nashville’s mayor.

But metropolitan Nashville is only 2 million people. It would be one of baseball’s smallest markets, like Kansas City, Milwaukee, or Cleveland. Then again, franchise moves were frequent in earlier years. They are rare now. In the last half-century, there have been only two relocations: the A’s now heading to Las Vegas and the 2005 Expos becoming the Washington Nationals.

Will the money for The 78 be found? Labeling it as a wise investment for taxpayers and a job creator is good. Both the mayor of Chicago and the governor of Illinois were lukewarm at best, expressing opposition to using tax money. And the current ballpark succeeded only because of the political pull of a popular governor.

But Baseball Commissioner Rob Manfred believes the White Sox will stay.

“Chicago is an anchor city for us,” Manfred said. “I think that the White Sox are in a difficult situation. I think the location of the stadium is tough, but I have confidence that things are going to work out in Chicago and that we’re going to continue to have two teams in Chicago.”39

Putting the argument in the rearview mirror, at least temporarily, the White Sox became the team with the most losses in modern baseball history in 2024. They won five out of their last six, but still finished 41-121, worse than the 1962 expansion New York Mets, a team constructed of every other team’s castoffs.

Grifol (28-89) was fired late in the 2024 season. So, just a few years after making the postseason in back-to-back years, they lost 100 in back-to-back years. They lost 12 in a row. They lost 14 in a row. They lost 21 in a row.

As the year 2024 drew to a close, Will Venable was hired as the new White Sox manager. Counting the interim hires, he becomes the sixth White Sox manager of the 2020s. He has been well-schooled under other excellent managers.

In a statement late in the 2024 season, Reinsdorf said everyone in the White Sox organization is extremely unhappy with the results. He called the year “painful,” but saw a silver lining. “What impressed me is how our players and staff have continued to work and bring a professional attitude to the ballpark each day.”40

How to evaluate the Reinsdorf era?

Of the 44 seasons under his ownership through 2024, two have been exactly at .500. There have been 21 winning seasons and 21 losing ones. Glass half-full or glass half-empty? There have been seven postseason years. Excluding the 2005 World Series run and the 2008 “Blackout” game won by Jim Thome’s home run, all the others ended in first-round exits.

There have been peaks. Sustained success has been rare. There were back-to-back playoff appearances in 2020 and 2021. There would likely have been back-to-back ones again in 1993 and 1994 had not the latter season been canceled.

The tide right now is out rather than in. Of the 12 seasons counting back from 2024, nine have been losers. There has been one year at .500 and only two winners.

Criticism of Jerry Reinsdorf is nothing new. In 1992, BusinessWeek called him “The Toughest #&?!%* in Sports.”41

Reinsdorf, the analysis said, “won’t win any popularity contests.” He challenges the rules of an old-boy network. He “didn’t charm his way to the top.” BusinessWeek called him the sports owner of the future, “an executive whose only business is sports, not a sport who is an executive in some other business.”

Leigh Allan authored a totally negative column in 2022 for SouthsideSox, dwelling on Reinsdorf’s use of tax law and calling him a “humongous liar.”42

Detractors have grown in strength and vehemence as the team’s play deteriorated in 2024.

“The Reinsdorf way is detached from the reality of modern baseball; it is feckless and loyal to everyone except the fans.”43

A piece by The Athletic said that while Reinsdorf had once been viewed favorably, his opinions had “calcified” over the years. He reportedly has refused to invest in “cutting edge amenities.”44

One anonymous source said: “I’m not sure if any owner loves baseball as much as Jerry. That’s why he can’t get out of his own way.”

On a technical level, the story went on to explain that Chicago had fallen behind in its use and detail of analytics. At times it had two sets of analytic data competing against each other. At other times, the recommendations were vague and general, rather than being specific.

What would be fair in evaluating the White Sox in the Reinsdorf era? Are the White Sox a major-market team because they are in Chicago? There are four markets with two teams: Chicago, Los Angeles, New York, and (through 2024) San Francisco-Oakland. In each of the dual-team markets, the trailing team has won exactly one World Series since the time Reinsdorf acquired the White Sox. The list: Mets in 1986; A’s in 1989; Angels in 2002; White Sox in 2005.

Although there are often numerous flip comments along the lines of cheapskate, the reality is that White Sox rank in the middle of the pack when it comes to payroll. Statista ranked the White Sox payroll on Opening Day in 2024 as 15th of the 30 teams. Sportrac compiled the 2024 White Sox payroll in 18th place.

USA Today put the White Sox 14th place in 2024 at $142,995,900.45 The next five teams lower than the White Sox were Minnesota, Kansas City, Milwaukee, Baltimore, and Cleveland, all of which were markedly better than Chicago in the season.

No less a figure than Kenny Williams, fired by Reinsdorf, had this to say: “I always thought over the years it was a little unfair when people would say, ‘All he cares about is making money.’ I’m sitting in the office and he’s saying, ‘I’m going to give you what I got.’”46

There are, of course, different ways to look at team spending. MLB.com lists the most expensive player contracts for teams, counting both free-agent signings and extensions given to current players. The White Sox are one of only two teams to never have a $100 million player contract. The Oakland A’s are the other team.

There are other teams that have paid $100 million or more to re-sign their own stars, but who have not paid $100 million for a free agent, as of 2024. That list includes the Rays, Reds, Pirates, Braves, Royals, and Guardians.

For Chicago perspective, the White Sox threw the World Series in 1919 and then went 40 years before the 1959 pennant, at a time when the American League was eight teams. The Chicago Bulls did not win a championship in the years before Reinsdorf. The Blackhawks have won six championships. The Bears have won nine titles. The Bears have not won since 1985. That team, like the ’83 White Sox, remains beloved.

The Cubs and the White Sox have each won three World Series titles. The Cubs’ drought, between 1908 and 2016, was a fan and media obsession. “Anyone can have a bad century.”

Titles are also hard to come by. The Brooklyn Dodgers of the 1950s, subject of book-after-book-after-book, with Hall of Famers Duke Snider, Jackie Robinson, and Roy Campanella, won a World Series exactly once before moving to Los Angeles. It was the same situation for the Atlanta Braves of the 1990s. Greg Maddux, Tom Glavine, and John Smoltz together produced one World Series title.

The Milwaukee Brewers of Robin Yount and Paul Molitor had no World Series titles. The Seattle Mariners of Ken Griffey Jr. and Randy Johnson never reached the World Series. That is also true for the Montreal Expos of Gary Carter, Tim Raines, and Andre Dawson.

In 1994 the Expos, like the White Sox, likely paid a steep price for the cancellation of the World Series. Montreal had the best record in baseball that year at 74-40 and was represented by five players in the All-Star Game.

In the nonfield aspects of the franchise, the White Sox under Reinsdorf have done just fine.

The White Sox, purchased for $20 million in 1981, are now worth $2.05 billion.47 Sports franchises of all kinds have escalated in price. The growing number of television channels demands more product. There are new revenue streams like the internet, alternative uniforms to sell and links to sports gambling – a real irony for a franchise where players threw a World Series. Mostly, though, it is supply and demand. The supply of franchises is limited. Demand is still there.

Founded in 2007, White Sox Charities has given away more than $47 million. Some 96 cents out of every dollar collected was given away. A car raffle, 50/50 drawings, scoreboard messages, selected bobbleheads and auctions of game-used material all benefit charity. There is a Sox Serve charity week. Among the projects helped is the Amateur City Elite athletes. Youths enrolled in the program graduate from high school at a 99 percent rate and 280 of them have earned college scholarships.48

The White Sox were also fairly out front with diversity. With Minnie Miñoso they were the sixth major-league team to integrate. Ted “Double Duty” Radcliffe, a legendary Negro League star, was tapped by the White Sox to throw out a ceremonial first pitch. Double Duty was past 100 at the time and lived to be 103. The team has a rich history of Latino players; and Ozzie Guillén was the first Latino manager to guide a team to a World Series victory.

Reinsdorf, along with Theo Epstein, Rick Hahn, and Bud Selig, is listed in the Owners, Front Office section of the Jewish Baseball Museum.

“I have always found Reinsdorf to be one of the most engaging, funny, thoughtful and honest people in sports,” said Ed Sherman, interviewing Reinsdorf in 2018 for the museum.49

Reinsdorf has received the Order of Lincoln award in Illinois. He was the Chicago Park District Chicagoan of the Year and named a Guardian of Children by the Jewish Council of Youth Services. He was given an honorary degree by Illinois College and the Award of Merit from Northwestern University. 50

Reinsdorf married Martyl Rifkin in 1956. They were a couple for 65 years. Reinsdorf remembered her working full-time and typing all his papers as he went to law school. He himself worked part-time making his way through law school.51 A leader in charities and the designer of the Chicago Bulls championship rings, Martyl Reinsdorf died at age 85 in 2021. The couple had four children and nine grandchildren.

Last revised: March 1, 2025

Sources

In addition to the sources cited in the Notes, the author consulted Baseball-Reference.com.

Notes

1 Rich Westcott, “Philadelphia Phillies Team Ownership History,” SABR.org. https://sabr.org/bioproj/topic/philadelphia-phillies-team-ownership-history/.

2 Bobby Nightengale, “Carl Pohlad and the Minnesota Twins: Four Decades of Highs and Lows,” Minnesota Star-Tribune, October 10, 2024. https://www.startribune.com/carl-pohlad-history-selling-minnesota-twins/601160271.

3 Chicago White Sox 2005 Media Guide, 5.

4 Phil Rogers, “Jerry Reinsdorf Says New Stadium Is a Must to Keep White Sox in Chicago,” Forbes.com, February 22, 2024. https://www.forbes.com/sites/philrogers/2024/02/22/jerry-reinsdorf-says-new-stadium-is-a-must-to-keep-white-sox-in-chicago/.

5 Phil Rosenthal, “Recalling Jerry Reinsdorf’s Come-From-Behind Victory 40 Years Ago for Control of the Chicago White Sox: ‘I’ve Never Celebrated Anniversaries of This Sort,’” Chicagotribune.com, January 29, 2021. https://www.chicagotribune.com/2021/01/29/recalling-jerry-reinsdorfs-come-from-behind-victory-40-years-ago-for-control-of-the-chicago-white-sox-ive-never-celebrated-anniversaries-of-this-sort/.

6 Ed Sherman, “Q/A with Jerry Reinsdorf: The Brooklyn Kid Who Grew Up to Own White Sox,” Jewishbasecallmuseum.com, May 18, 2018. https://jewishbaseballmuseum.com/spotlight-story/q-a-with-jerry-reinsdorf-the-brooklyn-kid-who-grew-up-to-own-white-sox/.

7 Asinwreck, “Forty Years of Jerry Reinsdorf, White Sox Owner,” Soxmachine.com, February 2, 2021. https://soxmachine.com/2021/02/forty-years-of-jerry-reinsdorf-white-sox-owner/.

8 “Jerry Reinsdorf,” Thefamouspeople.com, https://www.thefamouspeople.com/profiles/jerry-reinsdorf-51457.php.

9 Bob Vorwald, What It Means to Be a White Sox (Chicago: Triumph Books, 2010), 310.

10 Richard C. Lindberg, Total White Sox: The Definitive Encyclopedia of the Chicago White Sox (Chicago: Triumph Books, 2011), 94.

11 Vorwald, 310.

12 Mark Liptak “The Legacy of SportsVision,” SI.Com, May 13, 2020. https://www.si.com/mlb/whitesox/history/white-sox-the-legacy-of-sportsvision.

13 Vorwald, 310.

14 Vorwald, 310.

15 Vorwald, 310.

16 Vorwald, 310.

17 Jerome Holtzman and Peter Kendall, “Legislators Vote to Save Sox,” Chicagotribune.com, August 8, 2021. https://www.chicagotribune.com/1988/07/01/legislators-vote-to-save-sox/.

18 The White Sox agreement with the Illinois Sports Facilities Authority can be found at https://www.isfauthority.com/assets/management-agreement-with-all-amendments2.pdf. The White Sox lease can be found in its entirety on the Websites of the Illinois Sports Facilities Authority. Go to Business, then Finance, then Management Agreement with All Amendments.

19 Lindberg, 411.

20 Steve Wulf, “For Him the Belle Tolls,” Time, December 2, 1996.

21 Richard C. Lindberg, Total White Sox: The Definitive Encyclopedia of the Chicago White Sox (Chicago: Triumph Books, 2011), 411-412.

22 Bill King, “Jerry Reinsdorf: Staying True,” Sports Business Journal, May 20, 2013.

23 Vorwald, 311.

24 Ted Keith, “Don Fehr Looks Back 30 Years Later on MLB Strike,” Sports Business Journal, August 10, 2024.

25 Steve Wulf, “For Him the Belle Tolls.” Also see Michael Haupert “MLB’s annual salary leaders since 1874,” Outside the Lines, SABR, Fall 2012. https://sabr.org/research/article/mlbs-annual-salary-leaders-since-1874/.

26 Lindberg, 154.

27 Vorwald, 311.

28 Vorwald, 314.

29 Vorwald, 314.

30 Vinnie Duber, “Reinsdorf on Rebuild: Always Knew Plan Was Going to Work,” nbcsportschicago, September 21, 2021. https://www.nbcsportschicago.com/mlb/chicago-white-sox/reinsdorf-on-rebuild-always-knew-plan-was-going-to-work/183019/.

31 Jim Margalus, “Jerry Reinsdorf Gets His Man with Tony La Russa. The White Sox Are an Afterthought,” Soxmachine, October 29, 2020. https://soxmachine.com/2020/10/jerry-reinsdorf-gets-his-man-with-tony-la-russa-the-white-sox-are-an-afterthought/.

32 Ryan Taylor, “How Did Jerry Reinsdorf Conclude on the Dismissal of Rick Hahn, Kenny Williams,” nbcsportschicago.com, September 1, 2023. https://www.nbcsportschicago.com/mlb/chicago-white-sox/white-sox-news/how-did-jerry-reinsdorf-conclude-on-the-dismissal-of-rick-hahn-kenny-williams/504600/.

33 Ryan Taylor, “Jerry Reinsdorf Details Thought Process Behind Hiring Chris Getz as General Manager,” Sports.yahoo.com, August 31, 2023. https://sports.yahoo.com/jerry-reinsdorf-details-thought-process-232339195.html?fr=yhssrp_catchall.

34 Vorwald, 314.

35 Chicago Tribune, Believe It! The Story of Chicago’s World Champions (Chicago: Triumph Books, 2005), 30.

36 Bryan O’Neill, “Initial Plans Revealed for Purported New White Sox Park in The 78.” southsidesox.com, February 8, 2024. https://www.southsidesox.com/2024/2/8/24066466/initial-plans-revealed-for-purported-new-chicago-white-sox-park-in-the-78.

37 Associated Press, “Shooting at White Sox Game Likely Involved Gun Fired Inside Park,” August 28, 2023. https://www.espn.com/mlb/story/_/id/38278821/shooting-white-sox-game-likely-involved-gun-fired-park.

38 Phil Rogers, “Jerry Reinsdorf Says New Stadium Is a Must to Keep White Sox in Chicago,” Forbes, February 22, 2024. https://www.forbes.com/sites/philrogers/2024/02/22/jerry-reinsdorf-says-new-stadium-is-a-must-to-keep-white-sox-in-chicago/

39 R.J. Anderson, “Rob Manfred Weighs In on White Sox’s Future in Chicago with Jerry Reinsdorf Reportedly Open to Selling Team,” CBS Sports, October 23, 2024.

40 R.J. Anderson, “White Sox Owner Jerry Reinsdorf Has Noticed His Team’s Historically Bad 2024 Season, Too: ‘No One Is Happy,’” msn.com, September 13, 2024. https://ontapsportsnet.com/mlb/jerry-reinsdorf-statement-on-chicago-white-sox-2024-season-historically-bad

41 David Greising, “The Toughest #&?!%* in Sports,” Bloomberg.com, June 14, 1992. https://www.bloomberg.com/news/articles/1992-06-14/the-toughest-no-and-percent-in-sports.

42 Leigh Allan, “Jerry Reinsdorf: The Man Who Called Baseball a Public Trust and Didn’t Believe a Word of It,” Southsidesox.com. March 3, 2022. https://www.southsidesox.com/2022/3/3/22958768/white-sox-jerry-reinsdorf-the-man-who-called-baseball-a-public-trust.

43 Besnik Zekiri, “Jerry Reinsdorf’s Empty Rhetoric, Promises and Legacy of Failure Define a White Sox Franchise in Free Fall,” msn.com, September 11, 2024. https://www.msn.com/en-us/sports/mlb/jerry-reinsdorf-s-empty-rhetoric-promises-and-legacy-of-failure-define-a-white-sox-franchise-in-freefall/ar-AA1qqkfw.

44 Brittany Ghiroli and Ken Rosenthal, “An Owner ‘Who Thinks He Knows Everything’ Led the White Sox to Historic Disaster,” The Athletic, September 19, 2024. https://www.nytimes.com/athletic/5773947/2024/09/19/white-sox-failure-worst-season-history/.

45 Scott Boeck, “MLB Payrolls 2024: Full List of Every Baseball Team from Highest to Lowest,” USAToday, April 3, 2024.

46 Ghiroli and Rosenthal.

47 Mike Ozanian and Justin Teitlebaum, “Baseball’s Most Valuable Teams,” Forbes.com, March 28, 2024. https://www.forbes.com/sites/mikeozanian/2024/03/28/baseballs-most-valuable-teams-2024/.

48 White Sox Website. https://www.mlb.com/whitesox/charities.

49 Ed Sherman, “Q/A With Jerry Reinsdorf: The Brooklyn Kid Who Grew Up to Own White Sox.”

50 Chicago White Sox 2005 Media Guide, 6.

51 Interview with Reinsdorf for the Order of Lincoln award, found at IllinoisLincolnAcademy.org, laureates, 1997. https://www.youtube.com/watch?v=_6jNo44d60s.