An Early Pitching Pioneer

By Tony McClean
Updated: July 30, 2005

MLB LogosNEW HAVEN, Ct. — In the early twenties, Negro League baseball was dominated by strong pitchers. Hurlers like Smoky Joe Williams, Dave Brown, and Bullet Rogan were staples of their staffs.

For the Hilldale Daisies, who were the top team in the Eastern Colored League from 1923-26, their ace was a tall, lanky lefthander from Washington, D.C. Jesse “Nip” Winters was the league’s best pitcher.

During that four-year stretch, which included three pennants and a Negro League World Series championship in 1925, Winters went an amazing 87-26 (.770 win pct.) for Hilldale. The 6-foot-3, 225-pounder had the total package in his arsenal.

While he was somewhat wild early in his career, he had a great fastball. But his out pitch was a sweeping curve. He began his career in 1919 with the Norfolk Stars. However, Winters would make his first big mark against Rube Foster’s Chicago American Giants squad in 1921.

Pitching for the Atlantic City Bacharach Giants, Winters went a pedestrian 3-3 during the regular season. But it was his postseason that put him in the limelight. In a three-game playoff vs. Chicago, Winters tossed a 2-two shutout in Game One of the series which Atlantic City won 2-1.

Two years later, Winters left the Giants for Hilldale and his career along with the fortunes of the Daisies turned around. Winters went 10-3 and helped lead Hilldale to the 1923 Eastern League pennant. If you count his barnstorming numbers as well that year, Winters went 32-6 with a 3.03 ERA.


1924 turned out to be arguable Winters’ best season of his career. He went 27-4 and was named the league’s George Stovey Award winner as the league’s top pitcher. One of the highlights during the regular season came when Winters tossed a no-hitter against the Harrisburg Giants and future Hall of Famer Oscar Charleston.

Hilldale repeated as Eastern League champs and would go on to meet the Kansas City Monarchs is the first-ever Negro League World Series. While Hilldale would lose the best of nine series, Winters would put on a pitching performance for the ages.

Winters went 3-1 during the series with a minuscule 1.16 ERA. In fact, Winters tossed four complete games against the Monarchs. The highlight came in his duel with Kansas City ace Bullet Rogan in Game Five.

Winters allowed two runs and three hits to the Monarchs in the first inning, but he then allowed only one hit the rest of the way. Down 2-1 in the eighth, Hilldale loaded the bases with no outs. However, Rogan inducted two force plays and then struck out Winters to end the threat.

But the Daisies rallied in to tie and won the game in the ninth on a three-run, inside-the-park homer by Judy Johnson. At that point, Hilldale led the series 3-1 (Game Two ended in a 6-6 tie).

Winters and Rogan would meet each other again two days later. This time the Monarchs prevailed in a 4-3 win. It served as the beginning of Kansas City’s comeback. While Winters would go on and win another game, it was the Monarchs who took the series.


Winters and Hilldale would get their revenge the next season. The Daisies and Monarchs met again in the 1925 World Series. After a season where he went 21-10, Winters gained another complete victory in Game Four of the series.

However, he was falling out of favor with his manager Frank Warfield. Winters’ nickname was a not so subtle dig at his aversion to drinking. Despite going 15-5 in 1926 and 14-8 in 1927, Warfield would have to occasionally suspend the lefthander due to “not trying”.

He would later be traded to the New York Lincoln Giants in 1928, who a year later sent him packing to the Homestead Grays. Ironically, Winters would find his way back to Atlantic City during the tail end of his career.

While his career ended in controversy, Winters’ name should mentioned in the same breath of his contemporaries. During the postseason, especially during the 1924 World Series, Winters left a mark that may never be approached again.

NOTE: The Complete Book of The Negro Leagues, The Biographical Encyclopedia of The Negro Baseball Leagues, Only The Ball Was White, and The Encyclopedia of Negro League Baseball all contributed to this story.