22. Jimmy Ryan

When Jimmy Ryan arrived in Chicago in 1885, he joined a White Stockings squad that was the class of the National League. He didn't take long to find his footing, quickly establishing himself as a refined hitter who could do more than just slap the ball. In an era where home run power was a rare commodity, Ryan possessed a surprising sting in his bat. His residency in Chicago was defined by an ability to adapt as the game’s rules and distances evolved, serving as the steady link between the legendary era of Cap Anson and the burgeoning talent of the late 1890s.

The high-water mark of his tenure arrived in 1888, a season in which Ryan essentially owned the offensive categories of the National League. He paced the circuit in hits, doubles, and home runs—a rare "power-speed" trifecta for the time. While he was often overshadowed by the larger-than-life personalities of his teammates, Ryan was a tactical nightmare for pitchers, finishing in the top eight in OPS six different times. He wasn't a superstar in the modern sense, but he was a "solid contributor" who played at a high level for a remarkably long time, batting .308 during his lengthy stay in Chicago.

Beyond his bat, Ryan was a versatile asset in the grass. He was a primary outfielder but possessed the arm strength and athleticism to fill in on the mound when called upon, a testament to the iron man expectations of the 19th-century game. He collected 2,084 of his 2,513 career hits in a Chicago uniform, and survived multiple name changes for the franchise, from White Stockings to Colts to Orphans, remaining the one constant in an ever-shifting dugout.

The final walk toward the exit came after the 1900 season, as the "Old Guard" of the franchise finally began to disperse. Ryan played a few final seasons elsewhere, but his identity was forever tied to the West Side grounds. His 2,500-hit club status remains an elite benchmark that few in the history of the sport have reached, yet he stayed largely under the radar for a century.

Jimmy Ryan’s legacy received a long-overdue restoration in 2021 when the Cubs named him to their inaugural franchise Hall of Fame class.