Jim Leyland won plenty of games over the course of his 22 seasons as an MLB manager – 1,769 to be exact.
Leyland won a healthy number of playoff games on top of that, enough to win two American League pennants, a National League pennant and a World Series title. His impressive resume actually helped him earn him a spot in the National Baseball Hall of Fame, as he was voted in by the Contemporary Era Committee on Sunday.
But for all the success Leyland found in the dugout, one mishap still keeps him up at night.
Leyland's Detroit Tigers were leading the Boston Red Sox 1-0 in the ALCS, and they held a 5-1 lead heading into the eighth inning of Game 2. Future Hall of Fame designated hitter David Ortiz stepped into the box and blasted a game-tying grand slam, however, and Boston eventually walked off to win the pivotal contest.
The Red Sox sent the Tigers home packing by the end of the week, punching a ticket to the World Series in their place.
Leyland retired two days later.
A decade after the fact, Leyland spoke on the moment during a press conference at the Winter Meetings in Nashville. Bringing Joaquin Benoit in to face Ortiz instead of Phil Coke – who was also warming up in the bullpen – remains one of Leyland's biggest regrets, even though he continues to justify the decision to this day.
"That's the one that I've tossed and turned a little bit about," Leyland said. "I'm not sure today if I made the right decision or not. I think I did because I went to my best relief pitcher, the guy who I felt had the ability to make the best pitch, but it could be a question."
Leyland and the Tigers had just gone to the World Series in 2012, although they were ultimately swept by the San Francisco Giants. Detroit also lost to the St. Louis Cardinals in five games back in the 2006 World Series.
Fortunately for Leyland's Hall of Fame resume, he guided the Florida Marlins to a World Series crown in 1997. Leyland also won three straight division titles with the Pittsburgh Pirates in the early 1990s.
Ortiz's grand slam off Benoit instantly became one of the most iconic playoff moments of the 21st century. He would go on to win World Series MVP after leading the Red Sox to their third championship in 10 years.
More must-reads: