Of all the positions I've looked at, this one was the most difficult. Left field for the Yankees seems to be the spot that other outfielders switch to from other positions and it was difficult to even find one player who dedicated most of his time there. Ultimately, my choice came down to two very worthy Yankees - Hideki Matsui and Dave Winfield.
What decided it for me was the fact that Matsui spent the majority of his time with the Yankees in left field whereas Dave Winfield only played there for three of his eight seasons as a Yankee. There was also one more underlying fact.
As I mentioned earlier, the truly great ones rise to the occasion in the post season. While Winfield ultimately did that, it was with the
Blue Jays not the Yankees. On the other hand, Hideki Matsui more than rose the level of play on baseball's biggest stage.
In particular, he put on one of the greatest World Series performances anyone has ever had in the clinching game of the Fall Classic in 2009. He single-handedly clinched the win for the Yankees by going 3-for-4 with a HR and six RBI. As a Yankee, he was the consummate hitting professional and had a career batting average of .292. In the post-season, his average of .315 included hitting .615 in the aforementioned World Series.
His Yankee career was littered with performances such as that and forever endeared "Godzilla" to the Yankee faithful.