McKechnie was the first manager to win World Series titles with two teams (1925 Pittsburgh Pirates and 1940 Cincinnati Reds), and remains one of only three managers to win pennants with three teams, also capturing the National League title in 1928 with the St. Louis Cardinals.

He was nicknamed "Deacon" because he sang in his church choir and generally lived a quiet life.

[1] McKechnie made his major league debut in 1907 with the Pittsburgh Pirates, appearing in three games, before reemerging with the team in 1910 in a more substantial role.

However, Yankees manager Frank Chance thought McKechnie had a keen baseball mind, and had him sit next to him on the bench during games.

[2] Two years later, McKechnie got his first taste of managerial duties, when he served as player-manager of the Newark Peppers of the Federal League, leading the team to a 54–45 record.

McKechnie led the Pirates to 53 wins in 90 games to maneuver them into a third place finish in the National League.

Third place awaited the Pirates for the next two years, but the 1925 season proved a breakthrough as the Pirates went 95-58 and won the pennant, which was the first pennant for the club in sixteen years, led by future Hall of Famers such as Max Carey, Kiki Cuyler, and Pie Traynor.

Pittsburgh faced off against the Washington Senators, who had won the World Series the previous year while brought on fellow Hall of Famers in manager Bucky Harris, Stan Coveleski, Goose Goslin, Sam Rice, and Walter Johnson.

Amid rain and fog in Forbes Field, the Senators built an early lead with four runs in the first inning.

However, the Pirates responded each time Washington would score, and this included a 7-6 game going into the bottom of the eighth inning.

McKechnie's tenure in Pittsburgh unraveled the following year when several of his players thought part-owner, vice president and de facto bench coach Fred Clarke was undermining him.

Ownership struck fast and hard, releasing Bigbee and Adams and waiving Carey.

After the year ended, he replaced player-manager Bob O'Farrell, who was given a $5,000 raise to step down for McKechnie.

McKechnie was not nearly as successful in Boston as he was at his other managerial stops, but he managed to finish "fourth or fifth with teams that should have been eighth," according to baseball historian Lee Allen.

The bottom fell out in 1935, a season in which Babe Ruth returned to play in the city of Boston for the first time in 16 years, with Fuchs also giving him duties of vice president and assistant manager, although these were more ceremonial than anything.

According to Allen, McKechnie claimed that Ruth's presence made it nearly impossible to enforce discipline.

[8] Despite fielding essentially the same team that finished fourth a year earlier, the Braves crumbled to a record of 38–115, the worst record in modern National League history and the second worst in modern major league history.

According to one baseball reference work, McKechnie had a poor sense of direction, which did not improve when, as the Reds' manager, he began traveling by plane.

[9] He was hired as a coach to be the right-hand man of young Cleveland Indians manager Lou Boudreau the following year.