While in Orlando, Tinker developed a real estate firm, which thrived during the Florida land boom of the 1920s.

However, the 1926 Miami hurricane and Great Depression cost Tinker most of his fortune, and he returned to professional baseball in the late 1930s.

With the Cubs, Tinker was a part of a great double-play combination with teammates Johnny Evers and Frank Chance that was immortalized as "Tinker-to-Evers-to-Chance" in the poem "Baseball's Sad Lexicon".

Tebeau sold Tinker to the Great Falls Indians of the Montana State League in June.

Great Falls sold Tinker to the Helena Senators, also in the Montana State League, for $200 later in the season due to the team's financial insolvency.

[1] When he purchased Tinker's contract, Cubs manager Frank Selee was seeking a replacement at shortstop for Barry McCormick, who had joined the St. Louis Browns of the rival American League.

In addition to batting .266, he led the team with 146 hits, six home runs, 14 triples, and a .391 slugging percentage.

[18] Garry Herrmann, the owner of the Reds, identified Tinker as an ideal candidate to become his player-manager for the 1912 season.

[20] Herrmann began to listen to entreaties from his players, who wanted to retain Clark Griffith as manager,[19] but decided to hire Hank O'Day.

[21] Tinker finished in fourth place in the Chalmers Award voting following the season,[1] behind Larry Doyle, Honus Wagner, and Chief Meyers.

[28][29] Charles Ebbets, owner of the Brooklyn Dodgers, viewed Tinker as a good replacement for the released Bob Fisher, their shortstop in 1913.

The teams also agreed to swap players, with Earl Yingling and Herbie Moran going to Cincinnati and Dick Egan joining Brooklyn.

Charles Weeghman, the owner of the Whales, purchased the Cubs and consolidated his two Chicago rosters, retaining Tinker as his manager.

[43] Due to the high combined salaries of the Cubs and Whales, which included Brown and Roger Bresnahan, Tinker was tasked with releasing extraneous players from their contracts.

[2] In Mathewson's 1912 book, Pitching in a Pinch, he referred to Tinker as "the worst man I have to face in the National League.

The poem was written as a lamentation from the perspective of a New York Giants fan on how the team is consistently defeated by the Chicago Cubs.

[49] In December 1916, Tinker became part-owner of the Columbus Senators of the American Association, with Thomas E. Wilson serving as the principal owner.

[52] Tinker's wife committed suicide on Christmas Day, 1923, with a revolver during an apparent nervous breakdown.

[56] Tinker ended his involvement in professional baseball, focusing instead on his real estate ventures during the Florida land boom of the 1920s.

[5] Tinker convinced Reds owner Garry Herrmann to use his stadium in Orlando for their spring training site in 1923.

[58] However, his fortunes began to change in 1926, when the stock market receded and the 1926 Miami hurricane damaged significant areas of South Florida.

[59] During the 1930 season, Tinker returned to baseball as a coach for the Buffalo Bisons of the International League, who were managed by Clymer.

[60] Tinker became the manager of the Jersey City Skeeters of the International League after the dismissal of Nick Allen in August.

[61] The owner of the Springfield Ponies of the Eastern League attempted to convince Tinker to manage his team in 1931.

[64] During World War II, Tinker worked at Orlando Air Force Base as a boiler inspector.

[53] According to some tellings, Tinker and Evers did not speak to one another again following their fight for 33 years, until they were asked to participate in the radio broadcast of the 1938 World Series, played between the Cubs and the New York Yankees.

[13][65] However, in 1929, Tinker joined with Evers in signing a 10-week contract to perform a theatrical skit on baseball in different cities across the United States.

Complications of diabetes mellitus and Bright's disease left Tinker near death in 1936, when his physician believed he had 24 hours to live, and 1944, when he was placed in an oxygen tent.

[68][69] Tinker died at Orange Memorial Hospital in Orlando on July 27, 1948, his 68th birthday, of complications from diabetes.

[13] Tinker was posthumously inducted into the Florida State League Hall of Fame in 2009, in its inaugural class.