Obscure Spotlight: Troy O’Leary

When the Red Sox completed their improbable comeback in the 1999 AL Division Series against the Indians, from down 0-2 in the series, game 5 had two heroes: the first one, you know. Pedro Martinez came out of the bullpen and pitched six hitless innings on short rest, striking out eight.

The other, as Boston fans might remember, was outfielder Troy O’Leary. O’Leary hit a grand slam in the game’s third inning. And in the seventh, with the game tied at 8, the Indians elected to intentionally walk Nomar Garciaparra to get to O’Leary. Troy hit a near-identical home run to his earlier grand slam, this time a three-run dinger, to put the Sox up for good. He finished with 7 of the team’s 12 RBI.

I always found O’Leary to be vastly underrated. It could be because his best seasons were buried amid the height of the steroid era, when guys like John Jaha were hitting 30+ homers a year. He led the Red Sox with 28 dingers in 1999. His best years were in Boston (23 homers in 1998, 15 each in 1996-97) but he also appeared for the Brewers, who drafted O’Leary, for two seasons. His career ended with one-year stops in Montreal and Chicago. And hey, he also played 2004 with the Samsung Lions of the Korean Pro Baseball League.


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