John Sullivan

This article was written by Jacob Pomrenke

Lefty Sullivan had everything a pitcher could want: a blazing fastball, a knee-buckling curve, a disappearing spitball, and pinpoint control. The one thing he couldn’t do was field.

Because he felt dizzy every time he picked up a bunt – a lifelong heart condition cut off the flow of oxygen to his brain when he bent over too far – Sullivan’s considerable talent was overshadowed by the one weakness that major-league hitters could exploit. He pitched in just four games for the Chicago White Sox in 1919, making three errors in five chances, then sat on the bench during the fateful World Series that fall.

After refusing a minor-league assignment and engaging in a spat with owner Charles Comiskey, he quit the White Sox in 1920 and returned to the semipro ranks on Chicago’s South Side. The broad-shouldered, gregarious left-hander became a fan favorite in his hometown – Sullivan was considered the strikeout king of the city leagues for nearly two decades. His duels with ex-Cubs star Jim “Hippo” Vaughn were legendary, often drawing more than 5,000 fans to neighborhood diamonds on Sunday afternoons.

John Jeremiah Sullivan was born on May 31, 1894, to Jeremiah and Anna (Meany) O’Sullivan. The Irish-born Jeremiah O’Sullivan, according to family lore, had killed an English police officer in retaliation for a relative’s death and fled to Canada.1 He was repeatedly questioned by authorities there and soon relocated to Chicago, where he met his wife and found steady work at a bank; his name was anglicized along the way.

John, one of six siblings, excelled at athletics despite the disapproval of his harsh father, who was a stickler for education. Even in an era of “no Irish need apply,” living wherever they could on the South Side, his parents were able to send him to the private Catholic high school St. Rita, where he starred in baseball and football.2 After working and playing in a Chicago industrial league for a few years, he attracted enough attention to sign with Wichita of the Western League in 1915. The 21-year-old Sullivan went 2-5 with a mediocre 3.72 ERA in 22 games. His fielding statistics there are unknown.3

He moved back home after the season to start a family with his new bride, Anna Conick, the strong-willed daughter of a Chicago police detective. Their grandson, James P. Sullivan Jr., said Anna’s father was a “lace-curtain Irishman … who was suspicious of everybody. But Lefty swept her off her feet. She just loved him. … She always called him Sully, which I thought was the coolest thing I ever heard of. Except when she got mad – then she called him John.”4

In Chicago Lefty rejoined the industrial leagues and began to make a name for himself as a pitcher. He worked odd jobs during the week and often earned a little extra cash by playing pool. He enlisted in the US Army in 1918 and became a star for the 86th Division team, based at Camp Grant, Illinois. During one mid-May game against a team from the nearby Great Lakes Naval Station, Sullivan outpitched future Hall of Famer Red Faber in front of a reported 12,000 fans.5 That caught the attention of Faber’s employer, the Chicago White Sox. When Sullivan returned from a quick deployment to France in the last throes of World War I, he was invited to spring training with the major-league squad.

At 25 years old in 1919, Sullivan was not considered to be a top prospect because of his advanced age for a rookie and limited professional experience. But his talent, while raw, was hard to deny.

More than 50 years after last facing Sullivan, Negro Leagues star Willie Powell remembered him well in an interview with author John Holway: “He’d beat any team in the world, pretty near, if he could field bunts. We’d keep bunting it down the third base line most of the time. … But you didn’t hit him too often. I never got a hit off him – I never got one hit off Lefty Sullivan. … God, he was something!”6

White Sox manager Kid Gleason liked the charismatic left-hander immediately – and the feeling was mutual. Gleason spent time teaching Sullivan a curveball and attempting to cure his long-standing fielding woes. When the season began, the pitching-rich White Sox opted to send him down to Louisville in the American Association for more seasoning. The headstrong Sullivan refused the assignment,7 in part because the American Association had just banned his best pitch, the controversial spitball, from being used. (The major leagues followed suit a year later.)

Instead, Lefty signed with a semipro team on the West Side of Chicago and dominated that circuit for most of the summer, racking up huge strikeout totals every week. In the few games he lost, it was said that batters “bunted him to death.”8

On July 17, 1919, journeyman pitcher Grover Lowdermilk suddenly quit the White Sox and went home to Olin, Illinois. Sullivan “was immediately located,” signed, and given an old uniform. He warmed up that day at Comiskey Park against the Washington Senators, but didn’t get in the game.9

Two days later, on July 19, he made his major-league debut — in a surprise start opposing future Hall of Famer Walter Johnson. Sullivan’s fielding reputation preceded him; major-league hitters wasted little time in exploiting it. In the second inning, Sam Rice tapped a bunt back to the mound and Sullivan proceeded to throw it to the farthest corner of right field, allowing two runs to score. In the fourth, Washington’s Howie Shanks laid down a bunt and, as the Chicago Tribune reported it, “though [Sullivan] had oceans of time to fire to first and retire his man, he simply held the ball in his hand and carried it back to the slab.”10 That was all for Lefty that day, as Gleason immediately yanked him. The White Sox, on their way to a second American League pennant in three years, rallied to win in 11 innings.

The pattern continued each time Sullivan pitched. For example, on August 14, he pitched two scoreless innings against the Red Sox at the end of a 15-6 loss. In his one attempt to field a ball, he threw it straight into the ground, nowhere close to first baseman Chick Gandil. No one – not even Sullivan, at the time – had heard of such a problem, let alone understood it. The press seemed mostly amused by his affliction, and always made sure to mention it when he pitched. After the White Sox clinched the pennant, Sullivan was given a start on September 26 against the Detroit Tigers, who bunted on him twice in the first two innings, then decided to “play it straight” after that.11 Sullivan made one error and was hit hard in a 10-7 loss.

He never made another appearance in the major leagues.

Sullivan watched from the bench as eight of his teammates were implicated in throwing the 1919 World Series to the Cincinnati Reds, in what became known as the Black Sox scandal. Although Sullivan wasn’t a part of the fix, his grandson said, “He must have known what was going on. But he never said one word about it. … All he would say is that whatever happened to Comiskey, Comiskey deserved.”12

Sullivan’s loyalties, like those of most players of that era, did not extend to the front office. And while he made friendships with pitchers Red Faber and Eddie Cicotte and catcher Ray Schalk that lasted the rest of his life, his rift with owner Charles Comiskey continued to grow in 1920. Sullivan was left behind on an Eastern road trip, having not pitched all season, and jumped the team in May.13 He later believed, according to his family, that the White Sox owner tried to “blackball” him from Organized Baseball, in part because of his loyalty to the disgraced Cicotte, whose involvement in the Black Sox scandal was never questioned. In truth, players had little leverage against management in those days – especially with the reserve clause in effect, which permanently bound a player to the team that owned his contract. After Sullivan jumped the team, there was nowhere else in Organized Baseball for him to go.

Sullivan carried that resentment with him – his grandson said the lifelong South Side resident “would rather go to Cubs games, when he was an old man, than give Comiskey a dollar. It was pure hate. … And Lefty was not that kind of a guy.”14

At any rate, Sullivan was more than happy to play baseball anywhere. He took a job with Fairbanks-Morse, a prominent auto manufacturer in nearby Beloit, Wisconsin, and pitched for the highly competitive company team during the summers of 1920 and ‘21. He and his wife, Anna, were still struggling to begin their family, having lost their first four children in infancy to lung and heart problems.15 The couple were heartbroken, but their devout Catholic faith helped them persevere. In 1922 a healthy son was finally born, named James Patrick. Three more kids followed – Anna Rita, Robert, and Margaret. The daughters were both lifelong Dominican nuns, later working as activists in Washington, D.C., to help Salvadoran refugees, and Robert became a priest for nearly a decade until he requested dispensation from the Vatican in order to marry.16

Meanwhile, working as a salesman in his brother’s insurance company, Lefty continued to play baseball on Sundays for nearly 20 more years. The semipro leagues in Chicago were filled with major-league talent – in 1922, for example, Sullivan split two matchups against his old White Sox teammate, Dick Kerr, who was in the midst of a holdout against Comiskey, and won two out of three games against ex-Cubs southpaw Jim “Hippo” Vaughn, famous for his participation in the only “double no-hitter” in big-league history back five years earlier.17

Vaughn and Sullivan hooked up for many duels during that decade and the next, both of them bouncing around various teams sponsored by local philanthropists and politicians. Because of his crowd-pleasing strikeout totals, which were almost always in double digits, and his propensity to create drama when balls were hit back to him, Sullivan was arguably the most memorable character in his league. It was reported that fans “actually [went] out to games to see Lefty throw the ball away.”18

Sullivan never did shake his inability to field, but few semipro lineups were able to take advantage of his weakness. His stuff was simply too overpowering; many batters struck out just trying to lay down a bunt against him. In an era when few pitchers strove for strikeouts, Lefty soon realized how much he could benefit from them, regularly demanding a bonus from his team’s financial backers for each “K” he notched. And in the less regulated environment of the semipro game, which wasn’t under the same ethical constraints on gambling as Organized Baseball, Sullivan sometimes would place a $10 wager with an opposing fan if he happened to strike out 10 or more hitters – and he usually did.19 It was quite a lucrative career for Lefty, and he made more money there than he did while playing professionally.

By the mid-1930s, Lefty was the undeniable ace of the Chicago semipro leagues. His starts were often guaranteed by team management, especially when established major leaguers came around during offseason barnstorming tours. When Hall of Famer Dizzy Dean and his brother Paul brought their exhibition tour to the West Side after the 1934 World Series, it was Sullivan who relieved them on the mound in the middle innings, after the crowd had gotten a taste of the colorful Gas House Gang pitchers in action.20 Months later, Lefty was the starting pitcher against the vaunted Tokyo Giants and star pitcher Eiji Sawamura when Japan’s premier team stopped in Chicago during a US tour.21

Off the field, Sullivan decided – “on a wild hair” – that he wanted to make a run at politics. As his grandson explained, “He wanted to participate as an author, not a consumer, of the American dream. … And also, he was a little resentful of his immigrant father’s ignorance.”22 While Sullivan was well known throughout the city, his connections to the dominant Democratic Party machine in Chicago were limited; without its full support, he lost a race for alderman and was also unsuccessful in a bid for the state Senate. He later worked a number of politically affiliated jobs in Cook County, including a stint on the Traffic Safety Commission.23 While Lefty’s own political dreams were never realized, another grandson, John V. Sullivan, served as chief parliamentarian of the US House of Representatives from 2004-12.

Lefty Sullivan finally stopped pitching competitively in 1938, though he could always be enticed to show up for Old Timers Games, high-school fundraisers, or any other event related to the sport he loved. He joined a group called Baseball Anonymous, co-founded by his old White Sox teammate Red Faber, which assisted down-on-their-luck ballplayers with living expenses and other necessities. He kept in touch with many of his old baseball buddies, including Faber, Vaughn, Buck Weaver, and Ray Schalk, who all remained in Chicago after their careers were over.

In 1945, his son James – a former football player at Marquette University who later married his college sweetheart, Mary Claire, and became a steelworker – was shot down over Germany on a bombing mission while serving in the 8th Air Force during World War II. He was liberated from a prisoner-of-war camp after several months.24

The Sullivans celebrated the arrivals of 19 grandchildren and 48 great-grandchildren, though Lefty wouldn’t live to see them all. He enjoyed his last years, teaching his oldest grandsons (and anyone else in their Rainbow Beach neighborhood of Chicago) to play baseball, eating vanilla ice cream every night, and snacking on his beloved beef fat. But “he never drank a drop,” his grandson said, a product of watching his own father, Jeremiah, suffer from violent episodes of alcoholism for years.25 Lefty’s nutritional vices undoubtedly worsened his lifelong health problems – he suffered no fewer than six heart attacks, the last one proving to be fatal on July 7, 1958. He was buried at St. Mary Cemetery in Evergreen Park, Illinois.


A version of this biography appears in “Scandal on the South Side: The 1919 Chicago White Sox” (SABR, 2015). Click here for more information or to order the book.



Adrian Dominican Sisters, Adrian, Michigan.

Appleton (Wisconsin) Post Crescent, 1925-32.

Chicago Daily News, 1919-1958.

Chicago Defender, 1918-1935.

Chicago Tribune, 1915-1958.

Farrell, James T., Dreaming Baseball (Kent, Ohio: Kent State University Press, 2007).

Hammond (Indiana) Times, 1930-39.

Holway, John, Black Diamonds: Life in the Negro Leagues From the Men Who Lived It (Westport, Connecticut: Meckler Publishing, 1989).

Interview with James P. Sullivan Jr., November 7, 2010.

Interview with John V. Sullivan, November 8, 2010.

Sheboygan (Wisconsin) Press, 1926-38.

Southtown Economist, 1931-1958.

The Sporting News, 1919-1958.



1 Interview with James P. Sullivan Jr., November 7, 2010 (Hereafter James Sullivan Jr. interview).

2 Ibid.


4 James Sullivan Jr. interview.

5 Chicago Tribune, June 21, 1918.

6 John Holway, Black Diamonds: Life in the Negro Leagues From the Men Who Lived It (Westport, Connecticut: Meckler Publishing, 1989), 50.

7 Chicago Tribune, April 24, 1919.

8 Chicago Daily News, July 7, 1958.

9 Chicago Tribune, July 18, 1919. Manager Kid Gleason, desperate for pitching depth, persuaded Lowdermilk to return to the White Sox one week later.

10 Chicago Tribune, July 20, 1919.

11 Chicago Tribune, September 27, 1919.

12 James Sullivan Jr. interview.

13 Chicago Tribune, May 13, 1920.

14 James Sullivan Jr. interview.

15 Ibid.

16 Chicago Daily News, July 7, 1958; interviews with James P. Sullivan Jr. and John V. Sullivan, November 2010.

17 On May 2, 1917, Jim “Hippo” Vaughn of the Cubs and Fred Toney of the Reds both threw no-hitters through nine innings, the only “double no-hitter” in major-league history. Vaughn allowed a hit in the 10th inning and lost the game, 1-0.

18 Appleton (Wisconsin) Post Crescent, June 24, 1925.

19 Sheboygan (Wisconsin) Press, April 23, 1932.

20 Chicago Tribune, October 14, 1934.

21 Chicago Tribune, June 9, 1935.

22 James Sullivan Jr. interview.

23 Chicago Daily News, July 7, 1958.

24 Wisconsin Rapids (Wisconsin) Daily Tribune, October 16, 1945.

25 James Sullivan Jr. interview.

Full Name

John Jeremiah Sullivan


May 31, 1894 at Chicago, IL (USA)


July 7, 1958 at Chicago, IL (USA)

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