James Gilmore and Charles Weeghman of the Federal League, circa 1914 (LIBRARY OF CONGRESS)

Charles Weeghman

This article was written by Daniel R. Levitt

James Gilmore and Charles Weeghman of the Federal League, circa 1914 (LIBRARY OF CONGRESS)

James Gilmore, left, and Charles Weeghman of the Federal League, circa 1914 (LIBRARY OF CONGRESS)


In the early 1890s “Lucky Charlie” Weeghman descended on Chicago as a teenager seeking fame and fortune. A natural salesman, he soon became one of Chicago’s best-known restaurateurs and a celebrity man about town. Then the baseball bug bit. Perhaps more than any other individual Weeghman was responsible for even the limited success of the Federal League. His big-dollar signing of Joe Tinker away from Organized Baseball gave the new league its legitimacy and kicked off the war for players. By putting a new ballpark and his team on the North Side, he created the flagship team for the Federal League and a lasting legacy for baseball in Chicago. The team led the league in attendance and excitement, and likely outdrew the rival Cubs, still located on the city’s West Side. When the Federals shut down after 1915, Weeghman bought the Cubs and moved the team to his stadium on the North Side, the ballpark now known as Wrigley Field.

As an owner Weeghman spent money aggressively, both with the Federals and the Cubs. He won the FL pennant in 1915, and the Cubs captured the flag in 1918. But Charlie’s luck ran out shortly thereafter. His restaurants struggled during World War I, and he lost control of the team. Subsequently, he lost control of his restaurant empire. He tried unsuccessfully to reinvent himself several times, including in New York as a restaurateur. But in the end, his luck seemed to have deserted him.

Charles Henry Weeghman was born on March 8, 1874 in Richmond, Indiana, where his father, August, worked as a blacksmith. August owned a fairly extensive operation that included not just shoeing horses but larger undertakings such as repairing wagons. August was born in Bremen, Germany, and his wife, Eliza (née Eggemeyer), was a native Indianan. The two were married in 1873, and Charles was their first born; by 1900 he had two brothers and three sisters.1

After finishing high school in Richmond, Weeghman arrived in Chicago in 1893 around the time of the World’s Fair. He landed a job, initially as a “coffee boy” in King’s restaurant, a popular establishment for the late-night crowd in the Chicago Loop on Wells Street (then 5th Avenue). At King’s he learned the restaurant business, mingled easily with the clientele, and eventually moved up to headwaiter. In 1899 he married Bessie Webb, who had moved to Chicago from Janesville, Wisconsin, and was then one of the cashiers.2

Weeghman and Bessie struck out on their own a couple of years later. He had saved $200 and easily made the necessary connections and friendships with Chicago’s business promoters. Weeghman borrowed $300 and brought in a couple of partners, raising a total stake of $2,800. In January 1901 he opened his first restaurant at the corner of Wells and Adams Streets. Weeghman slowly built up a string of restaurants around Chicago, mostly self-service lunch places – what passed for fast food at the time. Often dubbed a “Baltimore Lunch,” the restaurant concept Weeghman popularized in Chicago consisted of chairs with a tray coming out of one of the arms – designed something like an airplane seat with the tray extended from the arm rest – was aimed at the clerks and other Loop employees with just a few minutes for lunch. Bessie proved a valuable partner in the business, managing much of the financial and day-to-day details that Weeghman couldn’t be bothered with and never really mastered. Six years later, with seven restaurants in his chain, Weeghman sold out to his partners for $50,000.3

With this new nest egg, Weeghman opened a restaurant on Madison, just west of Dearborn, later referred to as the “gold mine which made Weeghman.” Soon expanded to accommodate a movie theater and 108 chairs, the establishment was reported to serve 5,000 diners per day. Over the next half-dozen years, with financial backing from chewing gum magnate William Wrigley among others, Weeghman added another seven Loop restaurants to his portfolio and brought in his brother Albert to help manage the business. Weeghman also opened a popular billiard room and invested in several more movie theaters.4

By 1911 Weeghman craved the glamour and celebrity status of owning a major-league baseball team. Though he owned only three restaurants at the time, Weeghman put together a syndicate to purchase the St. Louis Cardinals. Owner Stanley Robison had recently died. Under the terms of his will, the team passed to his niece Helen Robison Britton and a reported sale price of $350,000 was placed on the franchise. Nevertheless, after Britton’s representatives had several meetings with Weeghman, she elected not to sell and held onto the team, much to the consternation of her fellow owners, who resented a woman in their midst.5

Almost three years later, Federal League President James Gilmore was looking for a rich, well-connected businessman to take ownership of the league’s Chicago franchise. The league, which in 1913 had competed as a mostly under-the-radar minor league outside of Organized Baseball, had decided to challenge the major leagues as a third major league for 1914. Otto Steifel and Phil Ball in St. Louis represented the first truly wealthy investors in a Federal League franchise. Gilmore understood that the league clearly needed more, and felt, in particular, that the Federals needed strong, aggressive ownership for their largest market, Chicago.

In Weeghman he found the perfect owner for his flagship franchise. Typical of a restaurateur, Weeghman was an aggressive marketer and glad-hander. He knew almost everyone in town, and his friends included many movers and shakers, such as Mayor Big Bill Thompson, and many with less than stellar reputations, like gambler Monte Tennes, later implicated in the 1919 Black Sox scandal.

Gilmore, a Chicago businessman himself, approached Weeghman on the golf course. By the time Gilmore came calling, the Weeghmans’ holdings had grown to a string of 12 restaurants, of which the most lucrative cleared over $50,000 in profits annually, along with some other business interests.6

“Now Weeghman,” Gilmore proposed, “I have a fine business opening for you, but we need more financial resources. We are going to reorganize the club with a capitalization of $50,000. If you will take $26,000 worth of stock, that will give you control of the club.”

“Are you sure $50,000 will be enough to finance this thing,” Weeghman queried his friend. “Won’t there be any other expenses that crop up when the club gets underway that will be likely to cost a lot of money?”

“Oh no,” Gilmore assured him, “all we want is $50,000. There won’t be any other expenses. That will be all the money we shall require.”7

After making the investment, Weeghman quickly realized that his initial instinct had been correct and that the club would require much more than $50,000. To help with the burden, Weeghman approached his friend William Walker, a local fish merchant. The two men and their wives had been friends for many years, and Walker supplied fish for Weeghman’s restaurants. The two had also recently purchased a small theater. Like Weeghman, Walker was a baseball enthusiast and self-made man, and when Weeghman outlined the proposition, Walker agreed it sounded like an attractive opportunity. After buying in, Walker stayed mostly in the background and let the suave, more outgoing Weeghman remain the front man. Weeghman now just needed a venue and a cast of players.

Fortunately, one of Chicago’s best-known baseball heroes was willing to listen to entreaties from the new league. Shortstop Joe Tinker, a star for Chicago’s great teams several years earlier, had recently been sold to Brooklyn and was haggling over his contract. Weeghman and Gilmore saw the Tinker situation as a huge opportunity and quietly approached him, offering an opportunity to return to Chicago. On December 27, 1913, Weeghman officially fired the war’s first big salvo. In an announcement that shocked the baseball establishment, Weeghman revealed he had signed Tinker to one of the largest contacts in baseball history, $36,000 for three years with $12,000 up front. The Federals had landed their first star. They could no longer be ignored.

Organized Baseball was not going to concede without a fight and tried to peel Weeghman away from the Feds, recognizing that the rest of the league would then be much weaker and unlikely to grow beyond its fringe status. Cubs owner Charles Murphy believed he had worked out a deal with Weeghman, Walker, and Tinker to quit the Federals for a payment of $60,000. According to his plan, Brooklyn would get Tinker back by paying him $32,500 in salary and bonus over the next five years, and Weeghman and Walker would receive $27,500, which would be funded by the major-league baseball owners.8

Weeghman was considering Murphy’s proposal because he was disappointed by the lack of players and money lined up by the other Federal League owners. Once they heard rumors of Weeghman’s impending desertion, they realized they needed to reel him back in quickly. Gilmore called a league meeting for Saturday, January 17, in Chicago at which they persuaded him to stay. In any case, Weeghman had long hankered to get into baseball and wanted more than a small payoff to fade away.

Weeghman didn’t have to wait long for another, more attractive proposition. Later that month Cleveland Indians owner Charles Somers and American Association President Thomas Chivington hoped to wrest Weeghman from the Federals by offering him an American Association team in Chicago. At least some major-league owners appeared willing to allow another team in Chicago if it would short-circuit the new league. Pushed by the financially strapped Somers, AL President Ban Johnson, and the other league owners agreed that granting an American Association team to Weeghman in Chicago was a small price to pay for eliminating the challenge of a third major league.9

On January 23 Pittsburgh owner Barney Dreyfuss called several owners with the message: “Information has just reached me that the Chicago Federal League man is ready to abandon that league and join hands with the American Association, placing a club in the North Side of Chicago. The American Association is ready to approve this. … Understand all American League Clubs are in favor of this scheme.” Seven of the eight National League owners indicated approval, the exception being Cubs owner Charles Murphy, who adamantly refused to allow another team in Chicago. Murphy’s veto effectively scuttled the plan to detach Weeghman from the Federals.10

Nevertheless, the Federals found signing major-league players much more difficult than they expected. At first they only went after players whose contracts had expired and were tied to their current team by the “reserve clause” only, a section of the player contract that required players to re-sign with their existing teams. The courts almost unanimously had ruled against the enforceability of this clause, but as long as all the teams respected it, the courts’ rulings didn’t really matter. Now, however, the Federal League teams were trying to sign these players; no one more aggressively than Weeghman. In two well-publicized moves, he landed pitcher King Cole and catcher Bill Killefer.

Under great pressure from Organized Baseball, both jumped back to their major-league team with substantial raises. Organized Baseball, in a brilliant legal strategy, did not fight the enforceability of the reserve clause. Instead, under the guidance of Ban Johnson, they employed a strategy of simply ignoring Federal League contracts and re-signing any player who had signed with the Federals – by offering more money, telling the player the Federals were doomed to failure, and threatening to blacklist him from Organized Baseball. This worked in a surprising number of cases and forced the Federals to be the ones to initiate the court cases against the players for jumping their contracts. The players who re-signed with Organized Baseball often did better in court than one might have expected given the facts of the cases, due to generally better lawyers and the ostensible moral standing of the big leagues. The eventual ruling in favor of Killefer was a big blow to the Feds. Weeghman bitterly resented the court’s logic, saying, “I cannot understand such a decision.”11

Weeghman also still needed a place to play. As America’s second largest city, Chicago had the population to support a third major-league team, particularly since the Cubs still played in an old wooden park on the old West Side, and the fans resented the Cubs’ frugal, less than fan-friendly ownership. Weeghman recognized that the most logical spot to locate a baseball team was on the city’s North side. Chicago had a population of around 2.2 million in 1914 and roughly 800,000 of them lived on the North side, a population larger than any other city in America excepting New York and Philadelphia, and now accessible by two branches of the “L,” Chicago’s commuter trains. If Weeghman could tap into this market, he felt he could create a valuable baseball franchise.

Weeghman’s preferred site had long been identified as a potential ballpark location. He quickly worked out a deal with its owners, minor-league owner Mike Cantillon and his brother-in-law Edmund Archambault, leasing the site for 99 years at $16,000 a year for the first 10 years, $18,000 a year after that, and a $30,000 down payment.12 Weeghman still required another strip of land to build his intended ballpark. Fortunately, the parcel was owned by a friend of Weeghman’s – he knew just about everybody in the city – and he initially believed acquiring it would not be a problem. Weeghman would have an anxious moment or two, however. He ended up having to pay $25,000 for the small piece and closed it just in time. An agent for Organized Baseball later offered $40,000, but it was too late. With this strip of land now under control, Weeghman could finally start construction.13

Now that Weeghman had his site, he still needed to build a ballpark, and time was running short. To get the project started, he hired architect Zachary Taylor Davis, who had designed Comiskey Park, called the “finest ball park in the United States” by the Reach Guide. Weeghman had little time to spare and did not need a palace; he needed a good, functional ballpark in less than two months. Moreover, his Federal League adventure was beginning to cost more than even his readjusted expectations. “When this thing started, we sat down and figured out we could sign a ball team and have a nice, modest little park for an expenditure of $50,000. We’re in $125,000 already [including $40,000 in salary advances to players], and we haven’t started work on our grandstand. Walter and myself will each have $125,000 invested by the time the season opens.” This may even have been a low estimate: the construction contract for the ballpark came to $219,000.14

Amid great fanfare, groundbreaking finally occurred on March 4, leaving less than seven weeks until Opening Day on April 23. Weeghman also battled Organized Baseball’s owners and lawyers, who were searching for legal loopholes and using political pressure to hinder construction. Weeghman’s connections obviously helped the process, and he used season tickets as currency to reward and influence neighbors and politicians in the ballpark debate. Despite some tense moments, the ballpark was ready by Opening Day.

Weeghman’s Chifeds performed well on the field during the tumultuous 1914 season. He spent most of the year building publicity for his team and league, pursuing players, and sparring with Organized Baseball in the newspapers and in the courts. On the field, Weeghman’s aggressive team building resulted in a second-place finish in the eight-team Federal League. Moreover, the team drew the highest attendance in the league, and although actual attendance figures remain murky, the Chifeds almost surely outdrew the Cubs.

Throughout the summer of 1914 Charlie Weeghman remained in contact with his landlord, Minneapolis Miller owner Mike Cantillon. Weeghman and Cantillon each considered themselves dealmakers and discussed the various goings on in baseball and the condition of the Federal League and Organized Baseball. From their conversations all sorts of ideas arose as to how to end the struggle. Late in the summer Cantillon reported to National Commission head Garry Herrmann that he thought Weeghman could be weaned from the Federal League.15

On September 2 Weeghman, along with Gilmore, met with Cantillon at the Federal League offices. Cantillon distanced himself from official representation but expressed that he had had conversations with the National Commission and other minor-league owners. Among many items, the trio discussed amalgamating the Federals into the high minors and eliminating the major-league/minor-league draft, something Cantillon would have desired as much as the Federals. When the meeting ended, Cantillon felt he had the basis for a settlement: In outline the Fed owners would be allowed to buy into or move their teams into the existing high minors (or be bought out) and the draft would be eliminated.

On October 14 Weeghman met with Herrmann in New York. Herrmann opened by invoking the Elks: “Mr. Weeghman you are an Elk. I am Past Grand Exalted of the Order, which no doubt you are aware of.” After Weeghman acknowledged that he was, Herrmann bound them to secrecy and that the conversation “be between man to man and not to be repeated to a single person in case nothing comes of it.”16 Herrmann summarized his understanding of the possible settlement terms in a letter to Ban Johnson: The Federal League was ready to go out of business; several teams would be absorbed by the American Association and International League, and franchises in these high minors would be placed in Chicago, Brooklyn, and Pittsburgh. Weeghman responded that this wasn’t quite correct; that he wanted to buy the Cubs and Brookfeds owner Robert Ward wanted buy either the New York Americans or the Boston Nationals, both of which were rumored to have struggling ownership.

Momentum built for a settlement along these revised lines but was eventually scuttled for several reasons: The community ownership in the previously minor-league Federal cities did not want to give up their major-league dreams; the Cubs proved harder to purchase than expected; Ban Johnson was only a lukewarm supporter at best; and Sloufed owner Phil Ball also wanted to buy one of St. Louis franchises.

By mid-November, when it became clear that a settlement would not be reached, both sides resumed the struggle. In particular, the Feds reinvigorated their pursuit of star players. Their primary target was baseball’s top pitcher, Washington’s Walter Johnson. Earlier in the summer Johnson had rebuffed inquiries from the Federals after he had been promised a new contract in the $16,000 to $18,000 range. Weeghman assumed the lead in negotiations and dispatched Tinker, the Federal’s best recruiter, to woo Johnson to the Chifeds. Tinker’s timing was perfect. Johnson had just received his 1915 contract in the mail offering only $12,500.

When Tinker showed up on December 3, it took only 20 minutes to agree to a three-year contract at $17,500 per year with a $6,000 advance on his salary. With the signing of Johnson, the Federals could barely contain their glee, and other players quickly followed. Johnson’s signing with the Federals shocked Organized Baseball, which had grown complacent in the few weeks after the collapse of the peace negotiations. Senators manager and minority owner Clark Griffith traveled to meet with Johnson. After a long, grueling meeting Griffith persuaded Johnson to return to Washington for the $12,500 previously offered and promised he would get Johnson a better contract the following season. Most of the other players the Feds signed during the fall were also threatened and cajoled back into Organized Baseball.

In response to Organized Baseball’s hostile tactics in re-signing players contractually committed to the Federals, in January 1915 they filed in the court of Judge Kenesaw Mountain Landis alleging antitrust violations. Weeghman was only tangentially involved with the suit, but like the other owners, he too clearly needed some relief from the cash-draining status quo. In one fan-friendly contest to encourage offseason interest, Weeghman held a contest to select a team name. “Whales” was chosen as the winning entry.

The Federals were also looking to bolster their ownership ranks. Weeghman and Gilmore traveled to French Lick, Indiana, the resort community where wealthy New York brewer Jacob Ruppert spent a portion of the winter. Ruppert was known to be in the market for a baseball team and the Fed duo hoped to entice him into purchasing the Indianapolis franchise, which he could move to New York or its environs. Once again, the Feds fell short. Ban Johnson, who had been talking to Ruppert about buying the Yankees, put that deal back on track.

Once it got underway, the 1915 season offered little respite to the Federals. Most teams drew fewer fans than the year before, though the Chifeds remained the league’s premier franchise. On the field the Federals could boast few stars in the prime of their careers. But for Chicago, at least, the final weekend was intense, controversial, and spectacular.

Pittsburgh entered the weekend with leads of a half-game on St. Louis and 1½ games on Chicago. Moreover, Pittsburgh and Chicago were scheduled for a doubleheader in Pittsburgh on Saturday, and the final game of the season was scheduled between those same two teams Sunday in Chicago. After sweeping the Saturday games, Chicago gained a half-game lead on Pittsburg and a one-game lead on St. Louis. Because rainouts and tie games were not generally made up, the pennant could be won by percentage point differences even if two teams were effectively tied under the games in front or behind measure.

Thus, whoever won the Sunday game between Chicago and Pittsburgh would capture the pennant. Weeghman, however, had another idea. The scheduled Friday game between the two teams in Pittsburgh had been rained out; Weeghman suggested that the game be made up on Sunday in Chicago as a doubleheader. This was ingenious; he now only had to split a doubleheader to win the pennant, and if Chicago split and St. Louis won, he would still capture the pennant, literally by a percentage point. Pittsburgh naturally protested this proposition, but Gilmore sided with Weeghman, ruling that if Pittsburgh did not play a doubleheader, he would forfeit both games to Chicago.

On Sunday in Chicago in front of an announced crowd of 34,212 – the news reports mentioned that fans were crammed into every nook and cranny of the ballpark – the Whales lost the first game but came back to win the second, and the pennant, 3-0. In the aftermath of his pennant, Weeghman challenged the major leagues to include his Whales in the postseason. He even enlisted some Chicago politicians in his lobbying effort. Weeghman’s appeal, though, fell on deaf ears. Rube Foster, manager of the American Giants, the country’s best black baseball team, challenged Weeghman to a postseason series. Weeghman ignored the invitation.17

After the season the Federal League owners who were still solvent had little interest in continuing the battle. The final settlement negotiations were led from the Federals side by Newark owner and oilman Harry Sinclair and Gilmore. The Federals actually managed to cut a reasonably good deal given their lack of negotiating leverage. One of the key provisions of the eventual settlement gave Weeghman a short-term option to purchase the 90 percent of the Cubs owned by Charles Taft for $500,000. (The other 10 percent was owned by Harry Ackerland.)

While Gilmore and Sinclair were opening negotiations with the major-league owners, Weeghman suffered a family tragedy. On November 18 his 65-year-old father, August, committed suicide. Eliza was found unconscious and bloody on the floor, though she survived. The elder Weeghman had sold his business roughly seven years before, and then four years later he and Eliza moved to Chicago, where all six of their children lived. He worked in one of Charlie’s restaurants for a time, but eventually ill health required him to retire from this activity as well. August often complained about being bored and missing his friends. At one point he moved back to Richmond before eventually returning to Chicago. “Nervous unrest alone was to blame for his act,” Weeghman said. “My father was a blacksmith for years. I finally persuaded him to give up active work and come here to live with me. He had nothing to occupy his mind, and he frequently became despondent.”18

During his two years fighting Organized Baseball, Charlie Weeghman had nearly exhausted his financial resources. He now had an option to purchase the Cubs, but he and partner William Walker needed to come up with the $500,000 purchase price quickly. The National League kicked in $50,000 to help. For another chunk of the capital, Weeghman leaned on a couple of his restaurant suppliers for $50,000 each: J. Ogden Armour, whom he had already tagged for a loan in 1915, and chewing-gum magnate William Wrigley. But after raising roughly $350,000 Weeghman ran out of sources.

In desperation, Weeghman turned to Albert Lasker, a Chicago advertising executive whom he did not know personally, but was recognized as someone who could raise money quickly. Lasker agreed to ante up the necessary $150,000 on two conditions: He would be allowed to approve the board of directors, and Lasker’s personal attorney would be the team’s attorney. Weeghman had little choice but to accept. At the initial organizational meeting, Lasker vetoed one of Weeghman’s choices and demanded that Wrigley and Armour, whom he knew personally, be on the board. Sears Roebuck president Julius Rosenwald was also named to the board. Weeghman controlled the team, but he had powerful men sitting beside him.19

Years later Weeghman added some further remembrances. He said that another group led by industrialists Charles McCulloch and John Hertz offered $750,000 for the franchise, adding urgency to the deadline Taft had given him. Furthermore, Roger Sullivan, a Democratic Party bigwig, had not come through with a promised investment of $75,000, forcing Weeghman to borrow this amount from the bank on short notice. Once he owned the team, Weeghman moved the Cubs from their West Side Grounds to Weeghman Park.20

The Federal League settlement also left the former league’s owners responsible for their player contracts. This was little bit of a two-edged sword: On the one hand it made them liable for the contracts that were guaranteed for 1916; on the other, it gave them the opportunity to sell the contracts, and hence the rights to the player, to the highest bidder. Weeghman simply kept the Whales players and amalgamated them into the Cubs. Weeghman’s roster heading into 1916 effectively consisted of his FL championship team plus the 73-80 Cubs of 1915. He named Joe Tinker, his Chifeds skipper, to manage the team in 1916. Ever the marketer, Weeghman became the first owner to allow fans to keep foul balls that went into the stands.

Weeghman hoped to make a further splash and strengthen his team by brashly advertising his midsummer player moves. In July, with the team around .500, he purchased minor-league shortstop Chuck Wortman for a price he boasted was greater than the previous record of $22,500 paid for pitcher Marty O’Toole. In actuality, the cash outlay was likely less than half the reported amount as the transaction included several players, and in the promotional spirit of the times, these players would have been allocated overly generous dollar values. The deal was almost held up by one hiccup. For the players to be sent to the minors, they needed to clear waivers. Typically, under a sort of a gentleman’s agreement, teams would not claim players from other teams in these transactions. But because Weeghman was still a Federal League outsider, Pittsburgh’s Barney Dreyfuss had no compunction about claiming one of the players who had previously been a Pirate. The deal was quickly restructured.

That summer Weeghman also purchased first baseman Fritz Mollwitz from Cincinnati and three other minor-league stars: catcher Rowdy Elliott, outfielder Joe Kelly, and pitcher Paul Carter. Overall, the newspapers estimated, Weeghman spent around $80,000 for the five players (though this likely included the full $22,500-plus for Wortman), a huge amount in this post-FL year of financial retrenchment. Moreover, Weeghman publicly pursued Cincinnati infielder Buck Herzog, claiming he would pay top dollar for him, estimated in the press at around $30,000. President Garry Herrmann, however, chose to send Herzog to the Giants in return for receiving Christy Mathewson to manage the Reds.

The Cubs’ final record in 1916 of 67-86 was a massive disappointment. Weeghman had combined two teams, spent liberally for additional players at midseason, and then watched the team collapse over the last two months. For 1917 Weeghman wanted a new manager and star players. In his typical brash style as the winter trading season opened, he announced, “I came here with $100,000 to get a new manager and two new players for the Chicago Club.”21 Most of the speculation centered on New York manager John McGraw and Boston skipper George Stallings. Neither owner was willing to sell his manager, and it was unlikely that McGraw, anyway, would have been willing to go to Chicago in any case, at least without a significant ownership interest. Weeghman settled for Stallings’ lieutenant and Braves coach Fred Mitchell, acquiring his rights for cash and Joe Kelly. He also struck out on any major player acquisitions.

The Cubs improved slightly in 1917 to 74-80, and Weeghman again ginned up the publicity and cash machine for the winter meetings, announcing that he had an unprecedented war chest of $250,000. He was more successful than the previous year, landing the league’s best pitcher, Pete Alexander, and catcher Bill Killefer for $55,000 in one transaction – the highest price paid for players up to that point – and Braves hurler Lefty Tyler for $15,000 in another. He also offered $75,000 to Branch Rickey of the cash-strapped Cardinals for second baseman Rogers Hornsby but was turned down.

While the other NL owners liked the Cubs cash, they didn’t like Weeghman’s publicly announcing what players he was targeting as it gave those players an inflated view of their value, at least by owner standards. At a league meeting unattended by Weeghman (he was represented by team secretary Walter Craighead), Rickey, then dealing with a Hornsby holdout, denounced Weeghman, and the league voted to censure such public statements as detrimental.

In the war-shortened 1918 season the Cubs won the pennant, but what should have been a triumphant year for Weeghman turned into a personal disaster. His business empire was crumbling as many of the young men who worked downtown and ate at his restaurants joined the military or war-related industries. To raise cash, he sold his mansion at 5627 Sheridan Road for a war-depressed price of $80,000.

After the season the team’s board decided to force Weeghman out of his role as president. The season had been a catastrophe financially for baseball as a whole, and for the free-spending Cubs the red ink was that much larger. The loss of Alexander to the war effort with no financial compensation from the Phillies further annoyed the board. Weeghman’s failing business empire and his loss of focus on the team further solidified the conclusion of the directors. While longtime silent partner William Walker remained on the board, Wrigley, Lasker, and some of the other partners bought out Weeghman’s remaining stock. He was formally removed as a director in November 1920.

Freed from the Cubs management, Weeghman turned his full attention to his failing business empire. But it was too little too late. With roughly $150,000 in overdue debts owed to around 150 creditors, in August 1920 some friendly creditors petitioned the bankruptcy court to put Weeghman’s business in involuntary bankruptcy and appoint a receiver to preempt actions by more aggressive creditors. Weeghman realized he needed to reorganize and reached out to some of his larger creditors, who agreed to help bail him out, most notably Wrigley and the Buffalo-based L.R. Steel Service corporation. “I have known for more than a year and half that Charlie was almost on the financial rocks,” Wrigley said. “He is a fine fellow as a man and a friend and I stand by ready to lend him all the assistance possible.”22 In November the bankruptcy proceedings were formally dismissed by the court, and Weeghman remained in a senior executive role, though by this point he had very little equity left in the business.

Weeghman also experienced significant changes in his personal life in 1920 when he and Bessie divorced. The two had been separated since September 1919. In the settlement Bessie was awarded $400 a month in alimony and custody of their 8-year-old daughter, Dorothy Jane. Bessie had played a central role in Weeghman’s success, and there can be little doubt but that he missed her expertise and detailed understanding of business as he tried to rebuild his enterprises.

On February 15, 1922, Weeghman married 29-year-old Carol Osmund, a hat model who had gained a measure of fame in 1913 when she criticized society women for spending large sums on their outfits. She claimed she could show them how to dress fashionably for much less money.

By late 1922 Weeghman’s business was again struggling, and he was behind on payments to creditors. In December he surrendered his management position, and in February he sold what little stock he still held in the company, formally ending his association with the restaurant chain he had built and run. The company continued to struggle, and in 1926, with $150,000 owed to creditors, a bankruptcy judge put the company in receivership.

For his next adventure, Weeghman announced he was getting into horse racing. He also found himself hauled before a court in 1923 for operating The Tent, an exclusive nightclub on the North Side, without a license. In November 1923 Weeghman sold his Lake Zurich estate to Chicago underworld king Terry Druggan for $150,000, generally viewed as a bargain price considering Weeghman’s financial difficulties.

Several years earlier Weeghman had furnished his estate for a more nefarious purpose. In the early 1920s the Ku Klux Klan was actively seeking to expand its reach beyond its Southern base. The first consequential Chicago event took place in August 1921. Roughly 2,000 automobiles left Chicago in parade fashion, traveling to Weeghman’s estate, where around 12,000 Klansmen participated in the area’s first mass ritual. Whether due to this event or other causes, the Klan became influential in Chicago, holding meaningful power until late in the decade.23

Weeghman eventually gave up trying to make a comeback in Chicago and moved to New York, where he had the financial backing of three of his former brethren in baseball ownership, Jacob Ruppert of the Yankees, Harry Frazee formerly of the Red Sox, and Harry Sinclair. Despite the support of these heavy hitters, his restaurants never gained traction. In 1927 he opened a bar and grill on Fifth Avenue near 22nd Street that failed, as did subsequent attempts on East 59th Street and East 58th Street. Eventually, he took a job with Ben Marden at his famous Riviera Night Club in Fort Lee, New Jersey.

In October 1938 Charlie and Carol were vacationing in Hot Springs, Arkansas. As they made their way back to New York they stopped off in Chicago, staying at the Drake Hotel. On November 1 Weeghman suffered a stroke and died the next day. His body was shipped back to his hometown of Richmond, where last rites were held at the Stegall-Berheide funeral home.

Weeghman could never recover his magic after his first years with the Cubs. Perhaps Weeghman’s luck was destined to run out: Without Bessie’s attention to detail and his predilection for betting big without the necessary resources, the odds were eventually going to catch up with him. But for several years in the mid-teens Weeghman was one of baseball’s leading characters. Without him it’s unlikely the Federal League would have ever competed on the field against major-league baseball. And the Cubs almost surely would never have ended up on the North Side. They would have remained on the West Side until lured to the suburbs and a new ballpark in the mass exodus of teams from central cities in the 1950s and 1960s.



1 Records at Ancestry.com; Harvey T. Woodruff, “‘Lucky Charley’ Weeghman, President Chicago Feds,” Chicago Tribune, April 26, 1914.

2 Harry Neily, “Death Ends Meteoric Career of Charley Weeghman, Angel of Federal League and Former Owner of Cubs,” The Sporting News, November 10, 1938; Chicago Tribune April 26, 1914; “C.H. Weeghman, 64, Dead in Chicago,” New York Times, November 3, 1938; “Lucky Charlie Weeghman Is Dead at 64,” Chicago Tribune, November 3, 1938; Stuart Shea with George Castle, Wrigley Field: The Unauthorized Biography (Dulles, Virginia: Potomac Books, 2004), 18.

3 Harvey T. Woodruff, “‘Lucky Charley’ Weeghman, President Chicago Feds,” Chicago Tribune, April 26, 1914; Harry Neily, “Death Ends Meteoric Career of Charley Weeghman, Angel of Federal League and Former Owner of Cubs,” The Sporting News, November 10, 1938; Chicago Tribune April 26, 1914; “C.H. Weeghman, 64, Dead in Chicago,” New York Times, November 3, 1938; “Lucky Charlie Weeghman Is Dead at 64,” Chicago Tribune, November 3, 1938; restaurant-ingthroughhistory.com/2008/09/08/fast-food-one-arm-joints; Wrigley Field: The Unauthorized Biography, 18.

4 Harvey T. Woodruff, “‘Lucky Charley’ Weeghman, President Chicago Feds;” “Weeghman Seeks to Buy Cardinals,” Chicago Tribune, March 30, 1911; “Wrigley Maker of History in Chicago Trade,” Chicago Tribune, January 27, 1932.

5 “Weeghman Seeks to Buy Cardinals”; Handy Andy, “Hart Home from S. America,” Chicago Tribune, April 8, 1911.

6 The Sporting News, November 10, 1938, 11; Chicago Tribune April 26, 1914; New York Times November 3, 1938; Wrigley Field: The Unauthorized Biography, 18.

7 Baseball Magazine, September 1915: 56.

8 Unidentified dates from Charles Murphy, Herrmann Federal League Hall of Fame file.

9 Thomas Chivington to August Herrmann, February 3, 1914, Herrmann files, National Baseball Hall of Fame.

10 August Herrmann to Barney Dreyfuss, January 23, 1914, Herrmann files; Transcript of telephone conversation Barney Dreyfuss and Harry Hempstead, January 23, 1914, 5:00 p.m., Herrmann files.

11 Grand Rapids Herald, April 11, 1914: 10, from Stereoscope, Winter 2003, 6.

12 Sporting Life, January 10, 1914: 15; Chicago Tribune, January 23, 1914: 14.

13 Chicago Tribune, January 20, 1914: 10.

14 Chicago Tribune, February 15, 1914: B1; Washington Post, March 4, 1914: 8.

15 August Herrmann to Mike Cantillion, August 17, 1914, Herrmann files; Mike Cantillon to August Herrmann, August 19, 1914, Herrmann files.

16 August Herrmann to Ban Johnson, October 17, 1914, Herrmann files.

17 “Foster Wants Fed Series,” Chicago Tribune, October 4, 1915.

18 “August Weeghman a Suicide in Chicago,” Star Press (Muncie, Indiana), November 19, 1915; “August Weeghman Cuts Throat with Razor at His Chicago Home,” Palladium-Item (Richmond, Indiana), November 18, 1915; “Yearning for Home City, Chilled by Chicago Life, Weeghman Ended Life,” Palladium-Item, November 19, 1915.

19 The Reminiscences of Albert Davis Lasker, 1950, 68-75, in the Oral History Collection of Columbia University; John Gunther, Taken at the Flood: The Story of Alfred D. Lasker (New York: Harper & Brothers, 1960), 117-8; James Crusinberry, “Armour, Wrigley and Banker Cub Stockholders,” Chicago Tribune, January 16, 1916.

20 “Half Million in Cash on Deadline! And Cubs Are His,” Chicago Tribune, June 4, 1936.

21 “$100,000 for Two Cubs and a Manager,” New York Times, December 12, 1916.

22 “Wrigley Offers Weeghman Aid in Difficulties,” Chicago Tribune, August 12, 1920.

23 Andy Oakley, “Boys in the Hoods,” Chicago Reader, September 27, 1996.

Full Name

Charles Henry Weeghman


March 8, 1874 at Richmond, IN (US)


November 1, 1938 at Chicago, IL (US)

If you can help us improve this player’s biography, contact us.