In the 1906 season, Flick played a league-leading 157 games. He led the league with 700 plate appearances, 624 at-bats, 98 runs scored, 22 triples, and 39 stolen bases (tied with John Anderson). However, Flick was "said to be dissatisfied with the team", and the Naps considered trading him to the Detroit Tigers for Matty McIntyre. Before the 1907 season, the Naps turned down a trade with the Tigers which would have exchanged Flick for the 21-year-old Ty Cobb. Hughie Jennings, the Tigers' manager, was tired of dealing with Cobb's abrasive behavior. The Naps refused to part with Flick, even in exchange for Cobb. They countered with Bunk Congalton, but the Tigers declined. Flick had been holding out but he signed a few days after the proposed trade. After Cobb was nearly traded away, Jennings attempted to repair the difficult relationships between Cobb and the other Detroit players. "Cobb is too good a hitter to let get away, when a little diplomacy will get the boys together", Jennings said. In the 1907 season, Flick again led the league with 18 triples.