If you're making a list of the toughest losses in Detroit Tigers history, you have to start with the winner-take-all postseason games:
Game 7 in the 1909 World Series
Game 7 in the 1934 World Series
Game 7 in the 1940 World Series
Game 5 in the 1972 American League Championship Series
Most Tigers fans don't remember any of those games, except perhaps the '72 loss to Oakland.
In recent memory, the toughest Tiger loss happened exactly two years ago today.
In 2009, the Tigers owned a seven-game lead in the American League Central in early September. But then the Twins got hot, and at the conclusion of the schedule the two clubs both were 86-76. So on the 6th of October, they played a one-game playoff for the division title.
Though mired in a controversy about his condition the previous weekend, Miguel Cabrera hit a two-run homer in the third, and the Tigers led 3-0 early. The Twins fought back for the lead, but Magglio Ordonez's solo shot in the eighth made the score 4-4. Brandon Inge RBI double in the 10th pushed Detroit ahead by a run, but Tigers reliever Fernando Rodney gave the run back in the bottom of the 10th; only a thrilling line-drive double play kept the Twins from winning then.
In the top of the 12th, the Tigers loaded the bases with two outs but couldn't score. And in the bottom of the 12th, the Twins finally pushed the winning across the plate and headed to their Division Series date with the Yankees (which they lost, as usual).
The pain from that game will never go away completely. But beating the New York Yankees would certainly salve the wound a little. Or maybe a lot.