Ken Williams

Over the course of a professional baseball career more than four decades long, Kenny Williams has done pretty much everything a person can do. After having navigated the grind of over a decade as a player, he made a smooth transition into the front office, where he came to be recognized as an astute baseball man. His career was capped by 22½ years as general manager and head of baseball operations with the Chicago White Sox, during which he led the 2005 team to its first World Series victory since 1917, ending the longest drought in American League history at 88 years.

Kenneth Royal Williams was born on April 6, 1964, in Berkeley, California. He was the only child of Jerry and Ethel Williams.1 His father, desiring to be a firefighter, sued to win the right to serve on the San Jose Fire Department, a legal fight he ultimately won, but which engendered no small amount of resentment among the other firefighters, not to mention the public at large.2 In fact, the legal challenge and the trial, which the young Williams attended, led to death threats and not long afterward, Williams recalled, his father gave him a .22 caliber handgun and taught him how to use it, if only to protect the family.3 Growing up in the Berkeley/Oakland area at that time, he could not help but be affected by the issue of race. His father’s willingness to go to court to secure his rights was not an isolated event. Williams’s biological mother was an early Black Panther and his godfather is the iconic sprinter John Carlos, whose raised-fist podium salute along with Tommie Smith in the 1968 Olympics was a defining moment in sports history.4 His father’s example, as well as those other strong and proud figures, provided the young Kenny with role models and experiences that arguably prepared him for the ups and downs he would experience during his baseball career.

Williams attended Mount Pleasant High School in East San Jose. There he shined in both football and baseball, and after the right-handed-hitting outfielder was drafted by the White Sox in the third round of the 1982 draft, he began his climb up the baseball ladder. After signing with the White Sox, he was assigned to the team’s Rookie League affiliate, the Gulf Coast White Sox. He hit .298 in 31 games there, scoring 19 runs while driving in 11.

At season’s end, Williams headed off to Stanford University, where he distinguished himself as a kick returner on the football team. He said he regrets having left Stanford early and regularly advises young prospects to remain in school and complete their degrees.5

Returning to professional baseball in the spring, Williams spent the 1983 season with the Appleton Foxes of the Class-A Midwest League. He hit .231 in 124 games, scoring 60 runs, driving in 53, and stealing 27 bases. He returned to Appleton at the start of 1984, and after hitting .286 with 23 runs scored and 26 RBIs in his first 38 games, he earned a promotion to Glens Falls of the Double-A Eastern League. In 97 games, he batted .246, with 35 runs scored, 47 RBIs, and 16 stolen bases.

In 1985, Williams spent a full season with Glens Falls. In 133 games he batted .250, with 87 runs scored, 66 RBIs, and 27 stolen bases.

The 1986 season saw Williams moving among three teams. He started the season with Birmingham in the Double-A Southern League, where he batted .331 in 68 games. While he struggled after being promoted to the Triple-A Buffalo Bisons, batting only .212 in 50 games, he nevertheless got an end-of-season call-up to the White Sox. Williams made his major-league debut on September 2 when he started in right field against the Kansas City Royals at Kansas City.

After popping out to first base in the top of the third, in the fifth Williams got his first big-league hit on a groundball single to third off left-hander Danny Jackson. He finished the day 1-for-4. For the White Sox, Williams batted .129 in 15 games, eight of which he started as he put in time in each of the outfield positions.

While he started the 1987 season back in Triple A, this time with the Hawaii Islanders of the Pacific Coast League, Williams was soon back in Chicago, where he enjoyed what proved to be his most successful major-league season. Playing in 116 games, he hit .281 with 11 home runs, 50 RBIs, and 21 stolen bases for a White Sox team that finished in fifth place in the American League West Division.

The 1988 season saw Williams again back in the minors, but not until after he had started the season playing third base with the White Sox. The experiment ended when he was sent down to the Triple-A Vancouver Canadians. After playing in 16 games with Vancouver, he was brought back up to the White Sox. For the season he hit just .159 in 220 at-bats. During 1989 spring training, Williams was sent to the Detroit Tigers for pitcher Eric King. He started the season with the Triple-A Toledo Mud Hens, but was recalled after playing in 14 games. In 94 games for the Tigers, he batted .205. The 1990 season was no better. In 57 games he hit .133 before the Toronto Blue Jays picked him up off waivers in mid-June. Things were little better in Toronto, where he hit .194 over the remainder of the season.

Williams began the 1991 season with the Syracuse Chiefs, the Blue Jays’ Triple-A team, but went to the Montreal Expos on waivers after only 15 games. After a short stint with Triple-A Indianapolis, he was promoted to the Expos, and while he hit .271 in 34 games, offering some evidence of why teams had perhaps continued to give him a chance, the Expos released Williams after the season. He made one final effort in 1992, playing in 36 games with the Denver Zephyrs, the Milwaukee Brewers’ Triple-A affiliate, but despite hitting .291, it was not enough to earn another shot in the major leagues and Williams’s playing career came to a close at the end of the 1992 season. He was 28.

Overall, Williams played in parts of 10 minor-league seasons. He appeared in 675 games, finishing with a batting average of .262, with 72 home runs, 330 RBIs, and 142 stolen bases. In 451 games over six major-league seasons, Williams batted .218 with 27 home runs, 119 RBIs, and 49 stolen bases.

Williams rejoined the White Sox organization as a scout in 1992, the first of a number of positions that exposed him to different aspects of team operations.6 In 1994 Williams was named a special assistant to White Sox Chairman Jerry Reinsdorf. He spent time in 1995 as a studio analyst for White Sox games on SportsChannel Chicago.7 Then in 1997 Williams was named vice president of player development, a job he held until October 2000, when he was named general manager of the White Sox, becoming at 36 the second youngest GM in the major leagues. (Only the Yankees’ Brian Cashman was younger.8)

The team Williams took over had a record of 95-67 in 2000 and finished first in the AL Central Division. After they were swept by the Seattle Mariners in the Division Series, general manager Ron Schueler stepped down. Reinsdorf named Williams to replace him. Williams immediately negotiated an extension with manager Jerry Manuel. (Together they became the first African American GM/manager duo.) Williams also began looking to strengthen the roster.9

By the time spring training arrived, Williams had signed free-agent catcher Sandy Alomar, traded for shortstop Royce Clayton, and traded for left-hander David Wells from Toronto. He then had to hold the line when Toronto attempted to rescind the deal after they discovered that Mike Sirotka, part of the deal, had an injured shoulder.10 Despite these and other less dramatic moves, the 2001 White Sox were unable to match the 2000 team’s performance. After a slow start, they were three games under .500 at the All-Star break and ultimately finished in third place in the Central Division at 83-79, a 12-game decline from the previous year.

During the next offseason, continuing to try to bolster the pitching staff, Williams traded for Pittsburgh Pirates starter Todd Ritchie, a workhorse who had started 33 games in 2001 and had won 35 games over the previous three years for the Pirates. But at 5-15 with an ERA of 6.06, the trade was a bust and none of the other lesser deals that Williams made had any great impact. Suddenly, just two seasons after winning the division and 95 games, the White Sox were a .500 team, finishing the 2002 season with a record of 81-81, although that was good enough for second place in a weak Central Division. Seeking to get the team back to where it had been when he started Williams again went looking for pitching, this time trading for Bartolo Colon, who won 15 games with an ERA of 3.87 in 2003, good enough to get him a new contract from the Angels as a free agent the following year. However, Colon did lead a stronger starting rotation as home-grown Mark Buehrle continued to develop, winning 14 games, while Esteban Loaiza, signed as a free agent, proved a big surprise, winning 21 games while posting a 2.90 ERA. Efforts to shore up the bullpen were unsuccessful, and the team improved to only 86-76, with the second consecutive second-place finish not enough to save Manuel’s job.

Having made no substantive progress in his first three years at the helm, Williams decided to go in a new direction. He hired his former teammate Ozzie Guillén as manager. Guillén, who had retired as a player after the 2000 season, immediately went into coaching, serving two years with the Montreal Expos before helping the Florida Marlins win the 2003 World Series. While hoping the fiery Guillén could help change the culture of the team, Williams continued his efforts to strengthen the team, especially the pitching staff.

While his first three years had not yielded success, the trades and free-agent signings Williams had made left little doubt that he was willing to pursue change in an aggressive manner. Also, his years as vice president in charge of player development had given him an in-depth familiarity with the White Sox’ and other teams’ prospect pools, and from the start he showed himself willing to trade young prospects for established players. That continued even into the season when in June 2004, in the continuing effort to bolster the pitching staff, he traded for starter Freddy García after having signed free-agent reliever Shingo Takatsu, who provided valuable bullpen help, in January. He also traded Aaron Miles for Juan Uribe in December 2003.

After the White Sox finished 83-79 in Guillén’s first year, Williams put together the final pieces of what would prove to be the 2005 World Series champions. In December 2004 he claimed Anaheim relief pitcher Bobby Jenks, who would emerge as the team’s postseason closer, off waivers. Seeking additional depth in the starting rotation, he signed free agent Orlando Hernández, who been traded away as part of the deal to get Colon back in 2003. Williams also made some important acquisitions to upgrade the offense. He signed free-agent outfielder Jermaine Dye and traded for outfielder Scott Podsednik, although his trade of Carlos Lee was not universally well received. And he signed free-agent catcher A.J. Pierzynski and second baseman Tadahito Iguchi in January. The additions of the last two years, coupled with holdovers Joe Crede, Paul Konerko, and Aaron Rowand, left the White Sox ready to make a run.

The team that broke camp in 2005 was markedly different from the one Williams had been handed when Reinsdorf promoted him to general manager in October 2000. Of the position players on the 2000 team, only first baseman Paul Konerko retained his place in the everyday lineup, while none of the starting pitchers were the same and only two – Mark Buehrle and Jon Garland – remained on the roster. Williams had engineered a massive overhaul, and from the beginning, the effort paid dividends. The 2005 White Sox got off to a strong start, going 17-7 in April, 18-10 in May, and 18-7 in June, and at the All-Star break they were 57-29, in first place in the AL Central Division, nine games ahead of the second-place Minnesota Twins. While they cooled off a bit in the second half, going 42-34 after the All-Star break, they ended the season winning eight of their final 10 games to finish at 99-63, the best record in the American League and only a single victory less than the St. Louis Cardinals.

In the postseason, the White Sox made quick work of their opponents, sweeping the defending World Series champion Boston Red Sox in three games before taking the best-of-seven League Championship Series vs. the Los Angeles Angels of Anaheim in five games to win the American League pennant for the first time since 1959. Then they swept the Houston Astros to claim their first World Series championship since 1917.

While the glow of the World Series victory would last well into the spring, the offseason did not allow Williams to rest. In December he released longtime White Sox star Frank Thomas. Although injuries had limited the future Hall of Famer to barely 100 games over the past two seasons, the parting was acrimonious as Thomas felt he was due the courtesy of a call from Reinsdorf as well as an effort to trade him. Meanwhile, in an effort to replace the big bat Thomas had wielded prior to his injuries, Williams had already traded Aaron Rowand and two other players for Indians slugger Jim Thome.

There were other lesser transactions as the team sought to stay on top, but it quickly became clear that as defending champions, the 2006 White Sox were in a different, unfamiliar, and uncomfortable position. Looking back in October, once the unsuccessful title defense was over, Williams talked about what the team had experienced, explaining, “You have the trophy and you have the rings, and people tend to look at you a little bit differently. They are a little bit more focused when they come out and play you.”11 But in fact, the White Sox title defense actually got off to a good start. While their Opening Day victory was followed by four straight losses, the team bounced back to win 22 of its next 27 games, and the White Sox entered the All-Star break with a record of 57-31, the second-best record in baseball, bested only by the Detroit Tigers (59-29). But the magic did not last. With a record of 33-41 after the break, the White Sox finished third in their division, six games behind the Minnesota Twins, who came on strong to finish first, one game ahead of the Tigers, who got the wild-card spot.

As the years went by and the memories of the 2005 championship season progressively faded, the White Sox struggled to replicate that accomplishment. During the seven seasons after the World Series win, with Williams as general manager, only the 2008 team made the postseason. But after winning the Central Division crown they lost to Tampa Bay Rays in the Division Series.

The years also included a number of unsettling incidents, most prominently the acrimonious departure of Ozzie Guillén in September of 2011 (a rift that was ultimately repaired12), and the later controversial decision by Williams to limit the access of players’ children in the locker room, a decision that led to the premature retirement of Adam LaRoche before it almost led to a player rebellion.13 None of this enhanced Williams’s public image or standing in the community, especially as things on the field only got worse. Nor did the October 2012 promotion of Williams to the position of executive vice president. Titles notwithstanding, he continued as head of baseball operations, while his former assistant general manager Rick Hahn assumed the role of GM.

The 2013 season saw the White Sox finish in the Central Division cellar, and while they quickly escaped last place, finishing fourth in 2014, that was the first of five fourth-place finishes in a row. They finished third in 2019 before returning to the postseason in the COVID-shortened 2020 campaign, securing the wild-card bid, but losing to the Oakland Athletics two games to one in the best-of-three series. The 2021 season saw the White Sox win 93 games, their highest total since the 2005 championship season, to win the Central Division, but they were defeated by the Astros in the AL Division series three games to one. In 2022 the team took a major step backward, finishing 81-81. Then in 2023, the bottom fell out: The White Sox were 38-54 at the All-Star break. On August 22, 2023, with the White Sox sitting at 49-77, owner Reinsdorf, in what he said “was one of the most difficult decisions of (my) life,” fired Williams and Hahn.14

In the eyes of many observers, it was a move long overdue. Over the course of Williams’s 22½ seasons at the helm, beyond the 2005 World Series title the White Sox claimed only three Central Division crowns, and a single wild-card bid in 2020. They finished second six times, third six times, fourth seven times, and fifth once, and not only did the 2023 team finish in fourth place with a 61-101 record, but the 2024 team set a modern-day record for losses at 121, eclipsing the 1962 New York Mets.15 It was not a sterling record, but one that left many wondering why Williams had not been fired sooner. But for a team whose last previous World Series championship had come in 1917, the 2005 crown loomed large. Years later, one baseball blogger called the 2005 White Sox “the greatest team no one remembers.”16 But the lack of recognition aside, in the eyes of Williams’s critics the increasingly distant championship season was all that kept him employed, especially when, as the years went by and the team proved unable to match it – or even come close, the calls for change had increased, with many observers and the members of the Chicago press believing that Reinsdorf’s “well-known loyalty was … the only thing saving” Williams’s and Hahn’s jobs.17

In response to the decision, Williams issued a statement that was professional and appreciative. He said, “I’m not really a ‘Statement’ kind of guy and had no intention of releasing one. That said, the volume of messages I have received in the wake of the news compels me to say something. First, I never knew so many people had my number.” He then went on to thank the fans, the players and staff, and everyone in the White Sox organization with whom he had worked, and especially Reinsdorf, for the opportunity to lead the team. He expressed both his pride in their championship and his disappointment that they had not been able to do more, and then closed with a personal note, saying, “I know that not everyone has warm and fuzzy feelings about me, but I tried to be honest and fair with everyone at every turn. At times, admittedly, maybe a little too direct. Sometimes I hit the mark and sometimes I missed the mark on my messaging, but there wasn’t a player who walked through our doors I didn’t care about or wished the best in his baseball career and family life.”18

Whatever criticism people might have had about Williams, there was no denying that he had spearheaded the effort that after almost 90 years, brought a World Series championship back to the south side of Chicago. It had not been easy, but he had done it, representing the team and the city in a professional, if often passionate, manner, while handling the critics and second-guessers who are an inevitable part of the job. While proud of the 2005 team and its accomplishment, like the fans he too had wanted more. In the end, he acknowledged mistakes, he took responsibility, but cherished what they had accomplished and the people he had accomplished it with.

One of the things that was not prominently mentioned at the end of Williams’s tenure but which can’t be ignored is the fact that in addition to the obvious pressures that were central to his job as head of the team’s baseball operations, Williams had to contend with another reality of the game, one that applied only to him. He was a Black man in a White man’s world. And whether his White Sox teams won or lost, that did not change. When Williams was named GM, he was the only Black GM in the majors, and only the third all-time, following Bill Lucas of the Atlanta Braves (1976-79) and Bob Watson (1995-98). The Yankees’ World Series win in 1996 made Watson the first and until Williams the only African American GM to win a World Series title. Williams never harped on any of this, but the challenges were real.

During an interview with a Chicago TV station in the summer of 2020, Williams shared a story of a conversation with a “very close white friend of his, an older man,” who asked Williams “What is it like to be Black?” Williams recalled that he responded, “It’s exhausting. And at times it has been more exhausting than others. At times you want to give up and you don’t see hope or a vision for a better future.”19 It was an unavoidable part of his life – a reality that was made all too clear soon after his appointment as GM when he returned home to “find a vulgar racial slur on the side of his house stating that no African American should run the White Sox, with the word White in all caps.”20 And it was no less an issue in his professional life. During his almost quarter-century in charge of White Sox baseball operations, he had witnessed many changes in the game, but one that had not occurred was a substantive change in the number of people like him – non-White males – who headed their team’s baseball operations. It was an issue to which MLB had increasingly paid lip service, especially the previous year in the midst of the George Floyd murder and the Black Lives Matter movement, but as Williams made clear in an unexpected set of remarks at the 2021 GM meeting, it was one that had long frustrated him.

Some of his colleagues were struck by the incident at the 2021 winter general managers meeting where Williams, having reached a “boiling point,” expressed the frustration that had been building up over two decades.21 He asked his peers to imagine if the situation he had lived with had been reversed, if for the past two-plus decades a White person at the meeting had walked into a room filled with Blacks, after having been promised annually that the racial makeup of the group would change, only to see the promises prove false. And then he asked forcefully, but plaintively, “Would you feel included? Would you feel as though you belonged?”22 Observers said that his comments made some feel uncomfortable, but Williams had felt he had to say his piece. He acknowledged later that over the 25 years that he had been attending the meetings there had been times when things were better, “[b]ut the last X number of years it feels like I’m on an island.”23

The unanticipated comments by Williams made an impact on many of his peers. Chris Antonetti, head of baseball operations for the Cleveland Guardians, called Williams’s comments “incredibly powerful,” adding that “[i]f someone was in that room and they weren’t moved by it and didn’t feel that it was a call to action for us to be better, than that would be alarming to me.”24 And Giants president of baseball operations Farhan Zaidi said that Williams’s comments “really struck a chord with me, his frustration and disappointment. Beyond calling the industry to task, which was totally appropriate, I just really felt for him as a person, knowing what he has seen and what he hoped things would look like 25 years ago, fast-forwarding it into the future.”25

Unfortunately for Williams, while his message may have been heard, he had little time left to try to achieve the changes he so desperately sought. But it was not a cause he would abandon. Instead, in the aftermath of his departure from the White Sox, Williams has found another venue in which to pursue and foster the opportunities that had for so long been denied people like him. Acknowledging that the move was “born out of frustration fatigue, and angst,” Williams became active in the world of diversity, equity, and inclusion, in an effort to “help open doors for minorities in business.”26 He is executive chairman and co-founder for the DEI Network and CLARA. CLARA is a tool to “mitigate bias in the hiring process, level the playing field for candidates, and help organizations find untapped talent.”27 The company says its mission is “to create access to opportunities and help people take advantage of those opportunities.”28 His work with CLARA represents Williams’s clear commitment to addressing some of the problems he spotlighted. Meanwhile he has not ruled out becoming involved in major-league baseball again. In an interview he gave in the summer of 2024, Williams indicated that if he “gets a call from a team he believes he can help win, he’ll listen,” but as he also told the reporter, “If I don’t get the call, then you can write about life after baseball.”29

Williams was divorced from his first wife, Jessica (Estrada) Williams, in April 2012. In July 2014, he was married to a CNN morning host, Zoraida Sambolin. With five children from his first marriage and with Sambolin having one son, Williams is deeply aware of the challenges young people face and so in his life after the White Sox he is working hard at CLARA to open up new opportunities for the next generation of Black leadership, in whatever field they may occupy. It is no small challenge. But he has taken on that kind before.

Last revised: March 1, 2025

Sources

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

Notes

1 Ken Rosenthal, “White Sox G.M. Brings with Him a Legacy of Courage,” The Sporting News, November 20, 2000.

2 Rosenthal.

3 Scott Merkin, “Ken Williams on Facing Racism, Hope for Future,” MLB.com, June 15, 2020: https://www.mlb.com/news/ken-williams-on-how-racism-impacted-his-career.

4 Merkin.

5 Gary Libman, “Now He Swings Deals,” Stanford Magazine, July/August 2001: https://stanfordmag.org/contents/now-he-swings-deals.

6 Libman.

7 Ryan Taylor, “Guillen Shares Kenny Williams Story after Winning in ’05,” NBC Sports Chicago, July 20, 2022: https://www.nbcsportschicago.com/mlb/chicago-white-sox/guillen-shares-kenny-williams-story-after-winning-in-05/328773/.

8 Libman.

9 Libman.

10 Libman.

11 Scott Merkin, “2006 Chicago White Sox Schedule,” Baseball Almanac: https://www.baseball-almanac.com/teamstats/schedule.php?y=2006&t=CHA.

12 Doug Padilla, “Kenny Williams-Ozzie Guillen: It’s Complicated,” ESPN.com, April 11, 2015: https://www.espn.com/blog/chicago/white-sox/post/_/id/23644/kenny-williams-ozzie-guillen-its-complicated.

13 Matt Bonesteel, “White Sox Almost Boycotted Spring Training Game Over Adam LaRoche,” Washington Post, March 17, 2016: https://www.washingtonpost.com/news/early-lead/wp/2016/03/17/white-sox-reportedly-almost-boycotted-spring-training-game-over-adam-laroche/.

14 “White Sox Fire President Kenny Williams, General Manager Rick Hahn,” SportsNet, August 22, 2023: https://www.sportsnet.ca/mlb/article/white-sox-fire-president-kenny-williams-general-manager-rick-hahn/.

15 The 1962 Mets, in the first year of the franchise, lost 120 games. The 2024 White Sox had a winning percentage of .253, however, compared with the Mets’ .250.

16 Adam Kaplan, “10 Years Later: A Look Back on the 2005 Chicago White Sox, the Greatest Team No One Remembers,” The Cover 3, March 14, 2015: http://www.thecover3.com/2015/03/10-years-later-look-back-on-2005-white-sox-greatest-team-nobody-remembers.html.

17 “White Sox to Look for Single Voice on Baseball Side After Firing of Williams, Hahn,” Street & Smith’s Sports Business Journal, August 8, 2023: https://www.sportsbusinessjournal.com/Articles/2023/08/23/chicago-white-sox-jerry-reinsdorf-fires-rick-hahn-ken-williams#:~:text=White%20Sox%20Assistant%20GM%20Chris,franchise’s%20%E2%80%9Cawful%20performance%20on%20the.

18 Joe Binder, “Kenny Williams, Rick Hahn Release Statements After Firing,” Sox on 35th, August 24, 2023: https://www.soxon35th.com/kenny-williams-rick-hahn-release-statements-after-firing/.

19 Merkin, “Ken Williams on Facing Racism.”

20 “Ken Williams on Facing Racism.”

21 Ken Rosenthal, “At GM Meetings, White Sox’s Ken Williams Expresses Frustration, Disappointment with MLB’s Lack of Progress in Front Office Diversity,” The Athletic, November 15, 2021: https://www.nytimes.com/athletic/2956711/2021/11/15/at-gm-meetings-white-soxs-ken-williams-expresses-frustration-disappointment-with-mlbs-lack-of-progress-in-front-office-diversity/.

22 Rosenthal.

23 Rosenthal.

24 Rosenthal.

25 Rosenthal.

26 Ryan Taylor, “Here’s What Former White Sox VP Kenny Williams Is Up To after South Side,” NBC Sports Chicago, May 7, 2024: https://sports.yahoo.com/heres-former-white-sox-vp-024226932.html.

27 CLARA Facebook page, https://www.getclara.io/people/kenny-williams.

28 “About Us,” CLARA Facebook page; https://www.getclara.io/about-us.

29 Daryl Van Schouwen, “Exclusive: Ex-White Sox VP Ken Williams Wants Another Title, Open to Return to Baseball,” Chicago Sun-Times, July 3, 2024: https://chicago.suntimes.com/white-sox/2024/07/03/former-white-sox-vp-ken-williams-wants-another-title-open-to-returning-to-baseball.