Nip Winters

For a brief period in the mid-1920s, Nip Winters was the best southpaw not just in the Negro Leagues, but perhaps in all of professional baseball. Armed with a bracing curveball, the lanky lefty baffled batters for 11 seasons before fading into seeming obscurity.

James Henry “Nip” Winters Jr. was born on April 29, 1899, in Washington, D.C., to James and Martha (née Jackson) Winters. Winters was the third of four children, two boys and two girls.1 James was an active child. Both he and his brother, Elmer, won a neighborhood playground “button contest” in 1909 that involved a 60-yard dash, pull-ups, and broad jumps.2

Winters got his start in baseball with the semipro LeDroit Tigers in Washington.3 By 1920, he began to play for the professional Norfolk All-Stars in nearby Norfolk, Virginia.4 Chappie Johnson, a veteran catcher turned player-manager-owner, assembled the team.

A write-up of an early start by the “likely looking youngster” foreshadowed things to come. Winters engaged in a pitchers’ duel, striking out six batters, but his control was lacking. In a 2–0 loss, he walked six and hit three batsmen.5 This combination of dominance and erraticism would define his career. Winters immediately stood out in Johnson’s outfit. On July 28, 1920, he pitched his first no-hitter, a 1–0 gem against the Winston-Salem Giants, in which he struck out 11.6

Winters stood an imposing 6-foot-2, making him a natural fit at first base.7 His ability to play the field serviceably allowed his bat to stay in the lineup when not on the mound. Winters proved proficient with the bat, slashing .289/.340/.448 in his professional career.

Constant change marked Winters’ early seasons in baseball. He played for whichever team would have him, and there are several reports of him jumping ship for a few games simply because he was in town. For instance, when Norfolk visited Baltimore to take on the Black Sox, Winters defected to the opposing club for one game. Incidentally, he still benefited Norfolk, making an error that allowed its only run to score in a 21–1 rout.8

Winters began 1921 with Norfolk, but his success quickly caught the attention of more prominent teams. When Johnson’s All-Stars stopped through Atlantic City, Winters battled the Bacharach Giants for 11 innings in a losing effort on June 27.9 By July 10, he had suited up for the Bacharachs. He bounced between the clubs while Norfolk was in town.

Winters announced his presence to the Negro National League on July 24 against the Indianapolis ABCs.10 He held his opponents to four hits and struck out 12 in a complete game. A local reporter colorfully remarked that his signature pitch, the curveball, “has a hook on it several feet wide [and] a drop that fooled the best.”11

Called “Jim” or “Jesse” in newspaper articles, Winters first appeared in 1922 on the roster of Johnson’s Philadelphia Royal Giants.12 However, it was with the Bacharachs that he broke out, tossing a no-hitter against Indianapolis on July 26. Winters turned in a phenomenal outing on both sides of the ball, striking out eight and contributing a two-run single in the 7–1 win. In many ways, the no-hitter was quintessential Winters—he also walked four, one of which led to the ABCs’ only run.

The 1922 season presaged the greatness that was to come. Winters proved himself a durable, dependable arm. He pitched a complete game in 10 of his 11 starts and earned a spot among Q. J. Gilmore’s All-Star selections in the Kansas City Star.13 While many of his teammates headed to California or Cuba for winter ball, Winters stayed stateside and played under Phil Cockrell in the hotel baseball league in Palm Beach, Florida.14

Winters followed Cockrell to the Hilldale Club for the 1923 season. The pair joined Red Ryan to form a fearsome big three in the Eastern Colored League’s inaugural season. Winters and Ryan led the league in ERA, and the trio placed in the top five in complete games, strikeouts, and innings pitched.15

Against the Doherty Silk Sox in September 1923, Winters came just two outs shy of his third career no-hitter. He began the contest by striking out the first five batters and remained perfect through 8 1/3 innings. Unfortunately, his wildness reared its head in the ninth as he walked Paddy Smith. Winters then cracked, allowing three straight singles and the go-ahead run. He finished the day with nine strikeouts but took the loss, 1–0.16

Winters’ drive to play all-season baseball led him to Cuba, where he played 14 games for Almendares. Unlike many of his teammates, including Ryan and Hilldale manager “Pop” Lloyd, who made Cuban baseball an annual tradition, Winters spent just two seasons overseas. He played for San Jose and Habana following the 1925 season.17

If 1923 was Winters’ breakout season, 1924 was a coming-out party for the entire Hilldale squad. Winters, Ryan, and Cockrell proved nearly unbeatable, amassing a 43–13 record in league play. Winters led the way with 20 wins, a 2.77 ERA, 114 strikeouts, and 208 innings pitched, which accounted for more than a third of the team’s total innings pitched that season. He also held his own at the plate, hitting four homers and tying for third on the team in slugging percentage.

Winters figured significantly in the “First Colored World Series” against the Kansas City Monarchs that same year. Taking the mound in four of the series’ 10 games, he notched three wins, only dropping a 12-inning battle in Game Seven. In total, Winters held the Monarchs to nine runs over 39 innings.

When not pitching, Winters was called upon to provide his services with the bat. He pinch-hit in three of the six games in which he did not pitch. In Game One, he plated Hilldale’s only runs with a two-run single in the ninth. He was equally valuable in Game Three when he walked to load the bases, setting up the tying run in a game that would end as a 6–6 tie. Even in the decisive Game 10, Winters gave the ball a ride before he was robbed of “a sure triple by a great running catch.”18

Hilldale lost the series, but Winters walked away a star. Columnist Dizzy Dismukes—a star Negro League hurler himself—mused, “Winters came near winning the championship single handed” and named the southpaw to his All-Star team.19

Winters and Hilldale enjoyed more of the same in 1925. The team battled Oscar Charleston and the Harrisburg Giants down to the wire and won its third straight pennant. Winters, once again, was the staff ace. He threw 200 innings in league play and logged a 3.02 ERA, best among ECL starters. He also had a .302/.362/.558 line at the plate.

In the rematch with the Monarchs for the world championship, Winters played a much smaller role in 1925. He took the ball in just one of the six games, contributing a complete-game victory in Game Four in Kansas City.

An altercation following Winters’ sole outing was indicative of the rocky times to come. On the team’s train ride from Kansas City to Philadelphia, Ryan allegedly offered Winters a pint of gin. When Winters, whose nickname “Nip” referred to his fondness for alcohol, discovered that the pint actually contained water, “the gang had to keep him from killing Red.”20

The following season marked the end of the good times for both Winters and Hilldale. He once again led the ECL in wins, but the club, which won the regular-season title, lost the post-season championship match to the Atlantic City Bacharach Giants. Winters ended the season on a high note, holding Earle Mack’s All-Stars, a barnstorming team boasting major-leaguer Lefty Grove, to one run.21

As Hilldale’s fortunes declined, so did those of Winters. His ERA ballooned to 4.14 in 1927, during which time he tried to jump to the Homestead Grays.22 However, he allegedly reported to his new team late and hungover. After a back-and-forth with Homestead manager Cum Posey, Winters returned to Hilldale.23

Although it seems Winters faced few immediate repercussions for his behavior, he was dealt to the New York Lincoln Giants in exchange for former teammate Ryan prior to the 1928 season. Newspapers reported the deal was part of “Hilldale’s policy to get rid of dissatisfied players and men who won’t stay in condition.”24 Winters got even for the trade in his first game against his former team and hit a “Ruthian wallop” in support of an 8–7 victory.25 He went on a run of 12 straight wins before hitting his first roadblock of the season.26

Winters’ success on the field did little to stop his seeming downward spiral. In early September, he was released by the Lincoln Giants due to his poor conditioning. Giants owner James J. Keenan alleged that Winters “completely ignored the training rules.”27 Winters finished out the season with the Homestead Grays.

Like his early years, the final seasons of Winters’ career could be best described as itinerant. He returned to the Lincoln Giants in 1929 but was no longer the dominant starter of the Hilldale days. He often pitched in relief of the ageless Connie Rector, who logged 188 innings as a 37-year-old that year.28 By June, Winters had been dealt to the Baltimore Black Sox, who already had seven pitchers on the roster. The surfeit of hurlers forced Winters to play first base and outfield for Baltimore.29 Contributing a career-high 24 RBIs across the two teams, Winters “developed into a superfine utility man” as the Black Sox won the pennant.30

The newfound skills were not enough to keep Winters in Baltimore, or pro baseball for that matter. He appeared with clubs from Burlington, Vermont, to Schenectady, New York, in 1930. He also reunited with Chappie Johnson north of the border as a member of his team in Quebec.31 Winters even made an appearance against Hilldale for “Old Timers Day” as a member of the Lawrence Stars of Bridgeport, Connecticut.32

The old-timer suited up for Hilldale as a last hurrah in 1931, but he lasted only until June, when he was cut from the squad for “failure to live up to club rules.”33 Winters finished the season with the Bacharach Giants and closed out his professional career by splitting his time between the independent Bees and his hometown club, the Washington Pilots, in 1932.34

Little is known about Winters’ life in the mid-1930s, but by at least 1942, he had settled in Hockessin, Delaware, and obtained work on Jacob Smith’s farm and at Hockessin Supply Company. At the farm, he met Jacob’s daughter Sarah, whom he seems to have married.35

Although Winters himself avoided the public eye after his playing days, the fans and sportswriters didn’t forget the slim southpaw. In 1952, he was featured on the second team of the Pittsburgh Courier’s All-America retrospective, and his name frequently came up in columns devoted to stars of yesteryear.36

Winters died after a brief illness in Wilmington, Delaware, on December 12, 1971, at the age of 72. Hundreds gathered to pay respects at his funeral in Wilmington.37 He is interred at Union Hill Cemetery in Kennett Square, Pennsylvania. In 2016, the Hockessin Historical Society erected a historical plaque at the former site of the Smith farm to pay tribute to “one of the top left-handed pitchers of his day.”38

Sources

All statistics are from Seamheads’ Negro Leagues Database, last accessed March 8, 2025, unless otherwise noted.

Acknowledgements

This article was reviewed by Rory Costello and Kim Juhase and fact-checked by members of the SABR Bio-Project fact-checking team.

Photo credit: Nip Winters, Trading Card Database.

Notes

1 US Census Bureau, 1910 Census. Accessed September 19, 2024, https://www.familysearch.org/ark:/61903/1:1:MKLJ-JVG.

2 “Boys Win the Button,” Washington Herald, August 12, 1909: 2.

3 Sam Lacy, “Stars of early Black baseball re-discovered,” Afro-American (Baltimore, MD), February 27, 1993: A8.

4 While some sources state Winters began play for the Norfolk Stars in 1919, no extant box scores can be found, and Winters himself recalled he “started playing ball about 1920.” Jesse “Nip” Winters, and John Holway. “Baseball Reminiscences of Washington’s Fesse ‘Nip’ Winters: ‘How I Struck Out Babe Ruth and Beat Lefty Grove.’” Records of the Columbia Historical Society, Washington, D.C. 71/72 (1971): 753, http://www.jstor.org/stable/40067797.

5 “Chappie Johnson’s Team Swamped,” Chicago Defender, July 3, 1920: 9.

6 “Pitches No-Hit, No-Run Game,” Chicago Defender, August 7, 1920: 6.

7 Some sources, such as James A. Riley’s The Biographical Encyclopedia of the Negro Baseball Leagues, list Winters as 6-foot-5. Seamheads and Baseball-Reference put him at 6-foot-2, and given photographs in which he appears close in height to Hilldale catcher Louis Santop, these are probably more accurate estimates.

8 “Sporting Dope,” Afro-American (Baltimore, MD), September 24, 1920: 11.

9 “Baseball Results,” New York Age, July 2, 1921: 6.

10 The Bacharach Giants were a professional independent club and an affiliate member of the Negro National League from 1920–22. Although they did not compete for the league title, they frequently faced off against league clubs, such as the ABCs.

11 “Jimmie Winters Holds A.B.C.’s at His Mercy,” Press of Atlantic City, July 25, 1921: 11.

12 “Bill Handy Signs,” Atlantic City Gazette-Review, April 29, 1922: 12.

13 “Gilmore’s All-Star Negro Team for 1922,” The Kansas City Sun, September 30, 1922.

14 “Shake Up in Hilldales,” New York Amsterdam News, January 24, 1923. Winters frequently played for the Breakers Hotel in Palm Beach, and he spent at least part of the winters of 1923-26 in Florida. “Britt Wins First Start in Florida,” Afro-American (Baltimore, MD), February 7, 1925: 23; “Stars That Shine,” Pittsburgh Courier, February 27, 1926: 10

15 These statistics should be taken with a grain of salt as the Seamheads database credits Hilldale with 61 games played in 1921. The other ECL teams played between 34 and 58 games.

16 “Doherty Silk Sox Shut Out Famous Hilldales,” New York Amsterdam News, September 19, 1923: 4.

17 While Baseball-Reference and Seamheads only list one season spent in Cuba, Jorge S. Figueredo’s Cuban Baseball: A Statistical History, 1878-1961 places Winters there twice more. W. Rollo Wilson also references him playing in Cuba in “Eastern Snapshots,” Pittsburgh Courier, February 6, 1926: 13.

18 “Kansas City Crowned World Champions,” Pittsburgh Courier, October 25, 1924: 6.

19 Dizzy Dismukes, “Dismukes Picks All-Star Team from Two Contending World Series Clubs,” Pittsburgh Courier, November 1, 1924: 6.

20 “Water Put in Bottle Fools ‘Nip’ Winters–Players on East Happy as Kids,” Philadelphia Tribune, October 10, 1925: 11.

21 “Hilldale Takes Two from Big Leaguers,” Pittsburgh Courier, October 9, 1926: 14.

22 As of March 8, 2025, Baseball-Reference credits Winters with two fewer earned runs allowed (as well as one more start), yielding a 4.04 ERA in 1927.

23 William G. Nunn, “‘Nip’ Winters Arrives and Departs,” Pittsburgh Courier, August 6, 1927: A4.

24 “Lincoln Giants Make Trade with Hilldale,” Afro-American (Baltimore, MD), April 21, 1928: 13.

25 Tom Lury, “Hilldale, Lincolns Divide,” Pittsburgh Courier, May 19, 1928: 17.

26 “Use Seven Hurlers as Cubans Win Two,” Afro-American (Baltimore, MD), July 28, 1928: 12.

27 “Nip Winters No Longer with Lincoln Giants,” New York Age, September 15, 1928: 6.

28 Rector’s career lasted until 1944 when he made four appearances with the New York Black Yankees at the age of 52.

29 Bill Gibson, “The Passing Review,” Afro-American (Baltimore, MD), July 6, 1929: 14.

30 W. Rollo Wilson, “National League Batting Averages Comparatively High,” Pittsburgh Courier, September 28, 1929: A4.

31 Christian Trudeau, “The Quebec Adventures of Chappie Johnson’s All Stars,” Our Game, Too: Influential Figures and Milestones in Canadian Baseball (SABR, 2022). Accessed January 7, 2025.

32 “Bridgeport to Face Hilldale on Saturday,” Philadelphia Tribune, September 18, 1930: 11.

33 W. Rollo Wilson, “Sport Shots,” Pittsburgh Courier, June 13, 1931: A4.

34 The Bacharach Giants, unlike the similarly named Bacharachs of Atlantic City, were an independent team formed by Harry Passon in Philadelphia. It is possible that Winters continued playing for the Bacharachs into 1933 and beyond as several newspaper articles contain lineups with his name. However, no box scores seem to exist for these games, so his participation cannot be confirmed. Rebecca Alpert, “Harry Passon: Philadelphia Baseball Entrepreneur,” The National Pastime: From Swampoodle to South Philly (Philadelphia, 2013). Accessed January 7, 2025.

35 This sketch of Winters’ later life is drawn from ancestry databases. On his WWII draft card, he lists Smith as his employer, and in the 1950 census, he is listed as a laborer at the Smith farm. Sarah is listed as Sarah Lewis on this census, but her marital status indicates that she was separated from her first husband. Interestingly, on Winters’ death certificate, Sarah is listed as his spouse, but on Sarah’s death certificate, Milton Lewis is listed as her spouse. She is buried under the name Sarah E. Smith Lewis. Winters’ obituary lists her as Sara [sic] Smith Winters. “James ‘Nip’ Winters, 72, Old Diamond Star, Buried,” Philadelphia Tribune, December 21, 1971: 21.

36 “Power, Speed, Skill Make All-America Team Excel,” Pittsburgh Courier, April 19, 1952: 26.

37 “James ‘Nip’ Winters, 72, Old Diamond Star, Buried”: 21.

38 Xerxes Wilson, “Remembering Hockessin’s almost forgotten baseball star,” News Journal (Wilmington, DE), January 1, 2016. Accessed January 8, 2025, https://www.delawareonline.com/story/news/2016/01/01/remembering-hockessins-almost-forgotten-baseball-star/78141848/.