We went from a tough call in center field to a much easier one in left field. Left field has historically been one of the strongest positions for the Red Sox. With players like Ted Williams, Carl Yastrzemski, Jim Rice, and Manny Ramirez playing the position over the years, it has been rare for a player to fly in under the radar. Even Mike Greenwell had some terrific seasons in left during his career. With all those stars, it was easier to find a player who had a good year but was never an All Star, and this one was easy for me. Troy O'Leary in 1999.
I remember O'Leary's 1999 season very well. He had been a favorite of mine since he quietly became the team's starting right fielder in 1995, stealing the job from the much more renowned Mark Whiten when he hit .308/.355/.491 with 10 home runs. His batting average fluctuated over the next few seasons, but his power numbers kept increasing up to the 1999 season. And that is when he had his best season from a power standpoint.
In 1999, O'Leary was a major offensive force in a lineup that really needed it since the home run leader each of the previous six seasons, Mo Vaughn, defected to the Angels as a free agent prior to the season. O'Leary ended up leading the team in home runs (28) and came within one RBI of the team lead (103). It was his career high in home runs and had 20 more RBIs than his second best season. He also chipped in 36 doubles and scored 84 runs. O'Leary was not a great defensive player, but he played well enough in left to not hurt the team and he did lead the league in putouts.
But as impressive as his regular season stats were, what really pushes him over the line for this pick was his postseason, in particular his clutch performance in Game 5 of the ALDS against the Indians. That game featured the two teams at two wins apiece and the Red Sox fell behind after a shaky performance from Bret Saberhagen. In the top of the third, with Boston behind 5-3, the Indians intentionally walked Garciaparra to load the bases for O'Leary to face Nagy. O'Leary hit a grand slam to put Boston in the lead 7-5. The Red Sox brought Pedro Martinez into a tie game, and it stayed tied until the seventh. The Indians again intentionally walked Garciaparra to put two runners on for Paul Shuey to face O'Leary. Again, he homered, and this time the Red Sox made it stick. So that is twice the Indians tried to avoid having Nomar beat them, only for O'Leary to homer both times, driving in seven runs.
O'Leary had been a solid player for a few years, but he became a very good player in 1999 and then had a memorable performance in the postseason. Unfortunately he would decline significantly and be pushed out after that.
Daniel Nava - 2013 (.303/.385/.445, 12 home runs, 66 RBIs)
Jonny Gomes - 2013 (.247/.344/.426, 13 home runs, 52 RBIs)