50. Kiki Cuyler

The mid-1920s saw a surge in offensive play across Major League Baseball, but few players, like Kiki Cuyler, matched the speed of that era. He not only hit well but also raced around bases with relentless speed, earning the nickname "The Flint Flash." For a brief, intense period at Forbes Field, Cuyler was at the top of the sport, combining contact hitting with exceptional speed to help lead his team to a championship.

Following a handful of brief September look-ins at the start of the decade, Cuyler fully broke into the everyday starting lineup as a rookie during the 1924 campaign. Thrust into the starting right field vacancy, he systematically dismantled National League pitching staffs, batting a spectacular .354 while lashing out 165 hits and swiping 32 bases in just 117 games.

That impressive debut immediately showcased his position as a top player, paving the way for a second summer that became one of the most outstanding individual seasons in franchise history. His real breakthrough in baseball came during the 1925 pennant race, when Cuyler delivered a spectacular, multifaceted offensive performance. He led all of baseball with a record 144 runs scored in the post-1900 National League and hit an impressive 26 triples—a league-high—among his 220 total hits.

He posted an impressive .357 batting average and hit 18 home runs, including an incredible eight inside-the-park homers, finishing second to Rogers Hornsby in the National League MVP voting. That fall, his legacy was cemented during Game 7 of the 1925 World Series, where he demonstrated remarkable resilience by hitting a crucial, bases-clearing double off Washington star Walter Johnson in the eighth inning, despite a heavy rain and muddy conditions at Forbes Field, helping secure the championship.

Despite his rapid rise to the top of the sport, his local narrative suddenly collapsed irreversibly. The emergence of future Hall of Famer Paul Waner pushed Cuyler to different outfield positions. In 1926, he delivered another strong season with 197 hits and 35 stolen bases. However, behind the scenes, Tensions simmered. Before the 1927 season, a toxic, low-variance personality clash erupted between Cuyler and new Pirates manager Donie Bush, mainly over the batting order and defensive roles. The conflict became so intense that Bush benched Cuyler for the entire 1927 World Series, leaving an astonished Pittsburgh crowd to watch from the stands as the Yankees swept the series in four games.

Following the season, Cuyler was traded to the Chicago Cubs.  With Pittsburgh, Cuyler had 680 hits, 115 doubles, 65 triples, and 44 home runs alongside a spectacular .336/.399/.511 slash line across 599 games.