Connie Mack

Cornelius McGillicuddy, Sr. (1862–1956), better known as Connie Mack, was an American professional baseball player, manager, and team owner. The longest-serving manager in Major League Baseball history, he holds records for wins (3,731), losses (3,948), and games managed (7,755), with his victory total being almost 1,000 more than any other manager. He managed the Philadelphia Athletics for the club's first 50 seasons of play before retiring at age 87 following the 1950 season, and was at least part-owner from 1901 to 1954. He was the first manager to win the World Series three times, and is the only manager to win consecutive Series on separate occasions (1910-11, 1929-30); his five Series titles remain the third most by any manager, and his nine American League pennants rank second in league history. However, constant financial struggles forced repeated rebuilding of the roster, and Mack's teams also finished in last place 17 times.

Connie Mack in "The House That George Built"
In 1914, Connie Mack had the opportunity to purchase George Ruth's contract from the Baltimore Orioles. He opted not to, due to financial reasons. Ruth regretted this decision for the rest of his life, convinced that had Mack or someother major league team picked him up in his prime, he'd have become a baseball superstar.