James Gilmore

This article was written by Daniel R. Levitt

James Gilmore (Bain Collection, Library of Congress)After several years in the military, Long Jim Gilmore spent his life as a successful, if conventional, businessman. For two years in the middle of his life, however, Gilmore was at the center of the baseball world as one of the most visible and quoted men in the industry. As president of short-lived Federal League, the last league to challenge the major leagues on the field of play, Gilmore fought to establish his league as a third major and gain acceptance in the prevailing Organized Baseball structure. For the FL’s two years of existence, 1914 and 1915, Gilmore gamely tried to sell the public on the new league, attract well-heeled owners, negotiate a détente with the established major leagues, and sign the game’s top players. Despite heroic efforts, the Federals folded after the 1915 season, accepting a buyout, and Gilmore returned to a less public life in private industry.

James Alexander Gilmore was born in Portsmouth, Ohio, on March 2, 1876, to Thomas and Jane (McCartney) Gilmore.1 When he was 6, Gilmore’s father, Thomas, moved the family, including three brothers and a sister, to Chicago due to his employment at Carson Pirie Scott & Co., a Midwest-based department-store chain. Gilmore attended Marquette, a school on the old West Side, and played a lot of baseball. Eventually filling out to 6-feet-3, Gilmore joined a couple of sandlot squads and eventually hooked up with the Chicago Wyandottes and other semipro teams, primarily as a pitcher. Teammates on the Wyandottes included Jack Hendricks, who had a brief major-league stint as a player and later manager in the major leagues, and Claude Varnell, a future minor-league owner who married Hendricks’ sister.

When Gilmore graduated, he accepted a job as a messenger for Armour & Co. at $3 a week; several months later he went back to demand $4 and was let go. Fortunately, Gilmore had two brothers in the coal business (the third worked for a ribbon company), and one helped land him a job at Crescent Coal and Mining for $7 a week, a nice increase.2

When the Spanish-American War came in 1898, Gilmore’s father told him, “I fought in the Civil War. So did three of my brothers. You are my only unmarried son. Go to War.”3 His initial tenure was rough. Gilmore caught malaria in Cuba and lost nearly 70 pounds in a month and a half. After a 13-month recovery, Gilmore decided to give the Army another try. He joined the 43rd volunteers at Fort Ethan Allen in Connecticut and was shipped out to the Philippines, another active war zone, in November 1899. On this second stint in the Army, Gilmore spent nearly two years as a commissary sergeant, earning $40.80 a month.4

Upon his discharge Gilmore resumed his prewar job as a coal salesman, at which he proved highly adept. He was a “good free off-hand talker, a good leader, a well-preserved man who would make a success, say in the railroad business.”5 Another admirer of his sales skills said: “Gilmore could not only convince you the moon is made of green cheese, but he could sell you a slice of it.”6 In 1910 his success at sales led him to the presidency of the Kernchen Company, a manufacturer of ventilators and ventilating engines. At the time, he was living in Chicago with a 39-year-old widow, Genevieve Williams, and her 22-year-old daughter. The next year, 1911, Gilmore and Williams were married in Louisville, Kentucky. The author has not been able to find reference to any additional children.

In the summer of 1913 the 37-year-old Gilmore was playing golf with his friend Eugene Pike, an investor in the Chicago Federal League franchise, then a first-year minor league unaffiliated with Organized Baseball and playing in rinky-dink venues in large Midwestern cities. For their round the two were joined by E.C. Racey, who also happened to be the treasurer of the team. The two admitted to Gilmore that the club was losing money, but sold him on the idea of a new league in large Midwestern cities that could compete with Organized Baseball. Over the next few weeks, as Gilmore contemplated the opportunity he not only decided that the Chicago investment could work, but that if he was going to invest, he wanted an active role in running the league. Gilmore and his associate Charlie Williams agreed to take an ownership interest in the team in exchange for assuming their share of the liabilities, mostly player salaries over the remainder of the season, which in the event came to about $14,000.

Moreover, at the league’s August 2 meeting Gilmore maneuvered himself into the presidency, although technically only on an interim basis. The league’s owners were frustrated with existing president and founder John Powers, who they felt had not sufficiently built publicity and had made a couple of bizarre scheduling and umpiring decisions. Gilmore’s salesmanship and fighting spirit appeared to be a perfect fit for what they were looking for. And in many ways he was.

When the league’s owners decided over the next several months that they wanted to challenge Organized Baseball as a third major league in 1914, they were woefully unprepared for the battle ahead. Most obviously they needed a more national footprint of franchises, much deeper-pocketed owners, star players, and major-league-quality ballparks. AL President Ban Johnson recognized the problem. “I cannot see how the Federals can expect to make much progress,” Johnson related. “You see they must build new ballparks, which will require a hefty outlay. Then, again, they must have a lot of money to induce star players to go with them.”7 Gilmore took on all these challenges with intelligence and enthusiasm and by Opening Day 1914 the league was better positioned than anyone could have reasonably expected.

Gilmore felt that the league in particular needed strong, aggressive ownership for its largest market, Chicago. He successfully addressed this by attracting Charlie Weeghman, a popular, wealthy, and well-connected local businessman. Weeghman owned a string of restaurants around Chicago, mostly self-service lunch counters — what passed for fast food at the time.

“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 under way 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.”8

After making the investment, Weeghman quickly realized that his initial instinct had been correct and that the club needed much more than $50,000. To help with the burden, Weeghman approached his friend William Walker, a local fish merchant. Weeghman would also build the league’s best ballpark, opening what is now known as Wrigley Field just in time for the home opener.

Gilmore also helped force the redistribution of franchises as he recruited wealthy owners. He persuaded bread manufacturer Robert Ward to take on the new Brooklyn franchise. Once the wealthiest men in all of baseball, Ward would help bankroll several of the struggling franchises over the next couple years. For a new Pittsburgh franchise, Gilmore landed Edward Gwinner, son a well-heeled contractor, and a bank president. The St. Louis franchise was strengthened through the addition of Phil Ball, a wealthy ice-plant manufacturer to its ownership ranks. Every franchise competing directly with major-league teams — Brooklyn, Chicago, Pittsburgh, and St. Louis — now had solid ownership. The other four that competed with high minor-league teams —Baltimore, Buffalo, Indianapolis, Kansas City — were owned by large syndicates of affluent locals, but only Baltimore could be said to have reasonably deep pockets.

Gilmore also proved successful on the ballpark front beyond Chicago’s Weeghman Park. Once he had the new owners in tow, one of his greatest achievements was prevailing upon them to invest the large sums necessary to acquire prime sites and construct new ballparks or gain control of quality existing venues.

Gilmore was also a tireless ambassador in recruiting players to jump to the new league. In late December 1913, the Federals effectively announced they were for real when they signed Joe Tinker away from the majors on a three-year contract for $36,000, a huge contract for the time. With open checkbooks, high expectations, and a belief in their mission, everyone connected with the Federals approached players in late December and January. In the hopes of making another big splash, Gilmore wired Ty Cobb a five-year contract offer at $15,000 per year (including the first year paid in advance), which would have made him the highest-paid player in baseball. Cobb parlayed this offer into a salary increase with his existing team, the Detroit Tigers. As the Federals soon discovered to their dismay, many players reacted similarly.9

In a more humiliating example, the Chifeds lost pitcher King Cole back to Organized Baseball. To avoid any appearance of impropriety when Cole signed his contract given his existing negotiations with the Yankees, Gilmore told Cole, “Now to avoid any trouble we will date these contracts December 30th, 1913.”10 In fact, the contract was signed on January 3.11 Gilmore and Weeghman were both embarrassed when this came out publicly. Overall, however, the Federals scrupulously targeted only players whose contracts had expired and were tied to their teams only by the generally non-enforceable reserve clause.

As the major leagues recaptured many of the players the Federals thought they had successfully lured away, Gilmore still imagined that a grudging accommodation with Organized Baseball could be arranged. Ban Johnson disparaged the new league both publicly and in private, but Gilmore believed that if he could just make his case in person, Johnson might be willing to enter into some sort of détente. Fortunately for Gilmore, his brother Charles was a friend of Johnson’s. When Charles first approached Johnson for a meeting with his brother, Johnson replied that “their interests were so wide apart it would probably be advisable not to meet him.”12 But Charles persisted, and Johnson reluctantly agreed.

According to Gilmore, the meeting ended with Johnson driving him over to the Chicago Athletic Club and promising to call the next day regarding a more formal follow-up summit after conferring with his counterpart, NL President John Tener. When another player the Feds thought they had landed, Fred Blanding, jumped back to Organized Baseball just days after Gilmore’s meeting with Johnson, Gilmore’s frustration boiled over. He believed that the Federals had acted honorably. “If the American and National Leagues ignore our contracts and fail to appreciate the spirit of sportsmanship we have shown, we will start the biggest of baseball wars.”13 But Gilmore would be sorely disappointed.

As Gilmore fumed, Ban Johnson gave an interview to the New York Evening Sun on March 5, 1914. He blasted not only the Federals but even the National League owners for an apparent willingness to negotiate with the new league: “I don’t favor these confabs. If the idea is to bring about a peaceful settlement of the present trouble in baseball the American League will put a stop to all negotiations. There can be no peace until the Federal League has been exterminated. Put it as strongly as you can that we will fight these pirates to a finish. There will be no quarter.”

A chastened, disappointed Gilmore renewed the effort to lure major-league players. At the beginning of March he wired Christy Mathewson an offer of $65,000 over three years — which would have made him the highest-paid player in baseball — to pitch and manage the Brookfeds. Mathewson spurned the huge offer, instead re-upping for a nice raise with the New York Giants. Cubs President Charles Thomas complained of an April assault by the Federals on his players: Gilmore met with Larry Cheney; other representatives made offers to Fred Mollwitz, James Lavender, Heine Zimmerman, Jimmy Archer, and Frank Schulte. None were successful.14

Gilmore spent the 1914 season frenetically traveling around the country to bolster his league. He met with existing and prospective owners, helped with various schemes to entice players to jump leagues, gave frequent interviews in local newspapers hyping the league, and at the end challenged the majors to have the World Series winner play the FL pennant winner. It wasn’t quite enough; the Federals lost a lot of money and never landed as many major leaguers as they needed or anticipated.

After the season several FL owners put out discreet peace feelers. The ensuing talks left Gilmore in an awkward position. As president of a putative major league and often in the news, he liked the salary and prestige of his job. He tried to stay in front of the negotiations by publicly announcing the league was willing to make peace at “fair and honorable terms,” but was “not standing on the doorstep, hat in hand.”15 At one point the Federal League office — surely a euphemism for Gilmore himself — released a statement that Gilmore had met in New York with Red Sox owner Joe Lannin, Cleveland owner Charles Somers, Philadelphia Phillies owner William Baker, and Braves owner James Gaffney. Gilmore was probably embellishing a short earlier meeting between Weeghman and Lannin.16

With this pronouncement Gilmore foolishly overplayed his hand. Over the next few days the referenced major-league owners could categorically deny the story and further ridicule Gilmore’s league. As partial information disclosed to the newspapers hampered discussions by causing the negotiating parties to worry about their reputations as information leaked out, Gilmore made an extraordinary admission to the press: “In the course of the next few months I may have to tell many lies. If I could avoid it I would, but there are some things that must be kept quiet, and in order to insure secrecy it is very often necessary to stretch the truth a little. I hate to do it, but there are times when the truth is not apt to be practicable.”17

By the end of November, the peace negotiations had collapsed, and the Federals redoubled their attempt to sign major-league ballplayers. Once again the bulk of the players Gilmore and Feds enticed to jump, most notably Walter Johnson, repudiated their Federal League contracts and re-signed with Organized Baseball. As their frustration level rose over the aggressive tactics and antitrust violations by the major leagues, in January, Gilmore and the Federal League owners filed suit in the court of Chicago federal judge Kenesaw Mountain Landis.

Gilmore also hoped to strengthen his ownership ranks. In late 1914 he and Weeghman traveled to the resort community at French Lick, Indiana, where Jacob Ruppert, a wealthy New York brewer known to be exploring buying into baseball, spent a portion of the winter. They hoped to persuade Ruppert to purchase one of the struggling FL franchises and move it to New York or its environs. Instead, Ruppert purchased the Yankees along with a partner.

Gilmore had a backup plan. He had found another wealthy investor, Kansas oilman Harry Sinclair, through Sinclair’s relationship with Pat Powers, a longtime minor-league executive who wanted to have a team in northern New Jersey. Gilmore maneuvered Sinclair and Powers into ownership of the Kansas City franchise, which was highly in debt and had apparently forfeited its franchise back to the league. Sinclair and Powers intended to transfer the franchise to Newark.

There was only one problem: Kansas City did not want to lose its team. On February 16 one of the team’s stockholders phoned Gilmore to grill him on what was happening.

“All I can say to you,” Gilmore responded, “is that I feel sure that everything will be all right, and Kansas City will retain its franchise. In fact it is a hundred to one shot.”

“What is the one shot?”

After receiving assurance he was speaking in confidence, Gilmore added the one wrinkle, and yet another long-shot contingency: “I have an option on the Indianapolis Federal League franchise, and am now going to New York and Pinehurst, North Carolina, and will do my best to have the men who want to take the Kansas City franchise take the Indianapolis franchise instead, and I have no doubt that will be accomplished.” Gilmore told the director to keep at the money-raising and added, “In the meantime if I am interviewed by reporters, I must of necessity deny anything but that the club has been transferred to an Eastern City.”18

Despite Gilmore’s reassurance that they would likely keep their franchise, the Kansas City directors recognized that Gilmore was in fact stalling them with the hope of making the transfer a fait accompli before they could react. A delegation from Kansas City descended upon Gilmore in Chicago on February 25. They had raised much of the money owed and intended to settle their debts. When the delegation demanded an accounting of their outstanding debt, Gilmore produced a paper showing $38,518. The delegation disputed this amount, arguing that some expenses were not the responsibility of the team and also pointing out that it was not offset by money owed to the team by the league. Gilmore told them it didn’t matter, “he would not accept the money if it was laid on the table.”19

The Kansas City mission then hastened over to the United States Circuit Court where they surprised Gilmore by asking for and receiving a temporary injunction against the transfer of the franchise to Newark. Not surprisingly, this flung much of the preparation for the season into chaos. Powers and Sinclair had already purchased a site in Harrison, New Jersey, a suburb across the Passaic River from Newark and needed to begin construction immediately on a 20,000-seat ballpark if it was to be ready by Opening Day. Powers had also made arrangements for the team to report to spring training in Texas less than two weeks later on March 8. Gilmore and Sinclair moved ahead as if the transfer would be sanctioned by the court. It also began to dawn on Gilmore that the Federals could lose the case, and he needed to seriously consider his previous suggestion of substituting Indianapolis, another club in financial difficulty, for Kansas City.

Gilmore would need to quickly invoke this contingency plan because the judge sided with Kansas City and agreed that Kansas City should be allowed to raise $40,000 to repay the league its cash advances. Stalemated on Kansas City, Gilmore, Sinclair, and Powers now formally turned their attention to Indianapolis. Gilmore along with two owners met with the Hoofeds board of directors on March 19 and eventually reached a deal to buy the team for $81,000, a pretty good payday for an effectively bankrupt franchise.

Despite the introduction of another well-heeled owner in Powers, the mounting losses during the 1915 season sapped much of the optimism that remained among the FL’s ownership ranks. Once again Gilmore spent the season shuttling around the league trying to encourage owners and fans alike, while trying to entice players to jump. Late in the season he began touting that the league was going to move into New York City for the 1916 season. Given that both Ward and Sinclair were rich enough to absorb further losses, this was not an idle threat. Years later Gilmore testified that this was just a bluff to force the Organized Baseball to sit down and discuss a settlement with the Federal League, but this seems unlikely. This was surely a serious option, at least until the unexpected death of Robert Ward in October.

If the Federals still had hopes of struggling through another season, the death of Ward surely ended them. The owners now hoped to settle for the best terms they could achieve. Gilmore played an active if secondary role in the negotiations that delivered settlement terms better than could reasonably be expected, with the Federal League’s owners receiving roughly $700,000 to agree to fold their league. With its demise, Jim Gilmore was out of a job.

The next year Gilmore and his wife quietly divorced in November, and Gilmore moved to New York. Gilmore’s ex-wife was awarded $2,500, the family furniture, and $250 per month for the rest of her life. The divorce, however, was alleged to have been “collusive” and was challenged and investigated by the court. At the time, when cause was still a condition of divorce, a husband and wife who wanted to separate but didn’t have a formal complaint might set up a situation where the husband appeared to commit adultery so that the court would grant a divorce. Gilmore and his wife were observed living together well after the stated dated of the adultery, bringing into question the legitimacy of the filing. Interestingly, the judge who looked to reopen the case, Judge Charles Foell, was the same one who ruled decisively against the FL in the Chief Johnson case in 1914, a seminal decision in the battle between the leagues. After some posturing that also included State’s Attorney Maclay Hoyne, the divorce was allowed to stand.

In October 1918 Gilmore reenlisted, two decades after he had first joined the Army, joining the Motor transportation Corps. “There is a fight going on and I simply can’t keep out of it,” Gilmore told the press. “I am 42 but still husky enough to whip a half-dozen Germans before breakfast.”20

After the war Gilmore returned to New York, where he became a stockbroker, his profession until the mid-1930s when he apparently retired. In early 1925 Gilmore met Texas heiress Electra Waggoner Bailey in Palm Beach, Florida, and two were married just three weeks later, on February 14. At the time of the wedding, Electra had just divorced her second husband. Gilmore and Electra annulled the marriage eight months later on September 11, officially because they had married too quickly after her divorce. But Gilmore’s sanguine comment on the annulment suggests the two had little interest in continuing the marriage: “We learned that under Texas law Electra was not allowed to marry so soon after securing a divorce from Weldon Bailey, so we went to Texas and amicably arranged the annulment.”21 Electra suffered from heart and liver troubles, and two months after the annulment she died from complications brought on by gallstones.

Gilmore became gravely ill in 1945 and was hospitalized in New York in December. He died on March 19, 1947, in Downey Veterans’ Administration Hospital in Waukegan, Illinois, from a stroke complicated by pneumonia. At some point along the way he had remarried and was survived by his third wife, Marie Boura Gilmore.22

As a precocious but obscure businessman, when he was 37 years old Jim Gilmore was thrust into the baseball limelight and national press. He found himself squaring off in public against some of baseball’s most press-savvy executives, men like Ban Johnson, John Tener, Charles Comiskey, and Garry Herrmann. Gilmore acquitted himself surprisingly well. He traveled extensively and untiringly to spread the message and merits of his new league to fans, players, and the press. That he made some missteps along the way serves mainly to highlight the extent of his challenge.



1 Ancestry.com. Illinois, Deaths and Stillbirths Index, 1916-1947 [database online]. Provo, Utah, USA: Ancestry.com Operations, Inc., 2011.

2 “J.A. Gilmore,” The Sporting News, January 22, 1914.

3 Harvey Woodruff, “James A. Gilmore, the Fighting President of the Federal Baseball League,” Chicago Tribune. January 18, 1914.

4 “J.A. Gilmore,” The Sporting News, January 22, 1914.

5 T.H. Murnane, “Feds Use Gaffney as Aid in Introduction to Boston Fans,” The Sporting News, August 19, 1915.

6 Frederick Lieb, “Federal’s Fate Haunts ‘Third Major’ Prospects,” The Sporting News, November 23, 1944.

7 Sporting Life, December 6, 1913.

8 “Famous Magnates of the Federal League — Messrs. Weeghman and Walker and How They Gained Success,” Baseball Magazine, September 1915: 56.

9 Charles Alexander, Ty Cobb (New York: Oxford University Press, 1984), 116.

10 Cole affidavit filed with The Federal League of Professional Baseball Clubs v. The National League, the American League, etc. case.

11 Farrell affidavit filed withThe Federal League of Professional Baseball Clubs v. The National League, the American League, etc. case; Cole affidavit.

12 W.J. McBeth, “Johnson Jottings,” Sporting Life, February 6, 1915.

13 Letter from Ban Johnson to August Herrmann, February 28, 1914, August Herrmann papers at National Baseball Hall of Fame and Museum; Washington Post, March 4, 1914.

14 “A New Backer for Federals.” Washington Post, March 3, 1914: 8; Thomas affidavit filed with The Federal League of Professional Baseball Clubs v. The National League, the American League, etc. case.

15 “Federals Seek Peace,” New York Times, October 2, 1914.

16  Ibid. “Baseball Peace Near,” New York Times, October 3, 1914; “No Quarter as Long as Gilmore Figures,” New York Sun, October 3, 1914; Boston American undated; “Presidents Deny Story,” Boston Post, October 4, 1914.

17 Unidentified newspaper clipping, August Herrmann Hall of Fame file; Handy Andy, “Feds to Discuss Offer of Peace,” Chicago Tribune, October 19, 1914; Sam Weller, “Gilmore Admits Deception Necessary in Baseball,” Chicago Tribune, October 20, 1914.

18 “The Kansas City Injunction Case in Court,” Sporting Life, March 20, 1915.

19 Ibid.

20 “Pvt. Jim Gilmore, Now,” Washington Herald, October 21, 1918.

21 “Race with Death Costs Rich Oil Man $14,000,” Wilkes-Barre Times Leader, November 16, 1925.

22 “James A. Gilmore,” New York Times, March 20, 1947; Ancestry.com. Illinois, Deaths and Stillbirths Index, 1916-1947 [database online]. Provo, Utah, USA: Ancestry.com Operations, Inc., 2011.

Full Name

James Alexander Gilmore


March 2, 1876 at Portsmouth, OH (USA)


March 19, 1947 at Waukegan, IL (USA)

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