While adding Matt Holliday to the Yankees lineup has its fair share of detractors and supporters, from Anthony McCarron, we learn that the organization could have added Holliday to the team 10 years ago via the ’98 draft. According to McCarron, “Holliday could have been a Yankee out of high school,” for the Yankees “considered drafting him in 1998 even though he had a scholarship to play football and baseball at Oklahoma State.” However, the Yankees thought that Holliday, a quarterback at Stillwater High, would opt for college over a major league career, and they ultimately chose Drew Henson over Holliday, based on those concerns. These same apprehensions allowed the Rockies to draft Holliday in the 7th round of the ’98 draft, as he fell due to questions surrounding his signability.
Of course, Holliday went on to play baseball in Colorado and has been one of the best outfielders in the National League since then, while Henson—along with Jackson Melian, Brian Reith and Ed Yarnall—was traded to the Reds in 2000 for Mike Frank and Denny Neagle. Henson was later reacquired from Cincy the following year and saw a total of 9 major league at-bats with the Yankees between 2002 and 2003 before pursuing a football career in 2004 (Henson, like Holliday, was also a quarterback). Interestingly, Holliday and Henson (I believe) are both free agents right now.
I wonder who the Yankees would rather pursue this time around…
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