Top Could-Have-Beens of NYY History: Drew Henson
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Henson was seen as a possible "can't miss" prospect in two different sports, but it wasn't meant to be in either.
Earlier in this ongoing "What Could Have Been" series, we took a look at some stars from the world of football that were at one time part of the Yankees' organization, but ended up finding more fame on the gridiron.
Of all the sports to have some crossover, it makes some sense that the most common pairing is baseball and football. There's less of an overlap in seasons than there are with basketball and hockey. There's also some common skills that work for both sports, meaning there's been tons of players who've plied their talents in both sports at one point in time. In the case of Drew Henson, he was good enough to make the top level of both sports, but not quite good enough to have a fruitful career in either.
Years In Yankees Organization: 1998-2000, 2001-03
How They Left: Released in 2004
Career MLB Statistics: 8 games, 9 plate appearances, .111/.111/.111, 1 single, -40 OPS+, -52 wRC+, -0.1 rWAR, -0.1 fWAR
Born in California in 1980, Henson was born the son of Carol and — football coach — Dan Henson. His family moved around a decent amount as his dad went from job to job, but they eventually settled in Michigan, where Dan had become an assistant coach for Eastern Michigan University. It was there at Brighton High School where Henson truly began to stand out on both the diamond and the gridiron.
As a high school senior, Henson hit .608 with 22 home runs in baseball, while throwing for 5,662 yards and 52 touchdowns as his team's quarterback. He was making waves nationally, having been named the National High School Baseball Player of the Year by multiple outlets, while the powerhouse likes of Michigan and Florida State recruited him to play football.
Henson eventually committed to Michigan for football, after fellow quarterback/baseball player Chris Weinke — himself a draft pick of the Toronto Blue Jays — opted to return to football and give up on professional baseball. However as far as baseball went, that did cause his draft stock to slide. Despite his status as the recognized best high schooler as a senior, many teams passed on him in the 1998 MLB Draft with the expectation that he wasn't going to play the sport long term.
One team that remained interested in him was the New York Yankees. Henson fell to the third round, where the Yankees selected him with the 97th overall pick. In order to get him in the fold long term, the Yankees agreed to let him go play college football in the fall.
On the football field, it took Henson a little while to get any meaningful playing time at Michigan, as he lost out on the starting quarterback gig to some guy named Tom Brady. He finally grabbed the starting spot to himself for the 2000 season, where he helped the Wolverines to a 9-3 record and a top-10 finish in the nation.
Over in baseball, Henson had very quickly impressed his Yankee coaches and teammates. Featuring some prodigious power, he OPSed .840 in 10 games in rookie ball in 1998, and followed that up with an .825 OPS and 13 homers in 69 games in High-A in 1999. By 2000, he was cracking the Top 25 prospects in all of baseball according to Baseball America.
Henson would briefly leave the Yankees system as he, along with Jackson Melian, Brian Reith, and Ed Yarnall were traded to the Reds for Denny Neagle in July 2000. However after wrapping up the 2000 season with the Reds, Henson was traded back to the Yankees in March 2001 for Wily Mo Peña. Shortly after that, he made his commitment to baseball fully, signing a six-year, $17 million deal with the Yankees. That meant he would forgo his senior football season at Michigan, but also a likely very high selection in the 2002 NFL Draft.
That's about when Henson began to stall out a bit. While he had steadily made his way through the minors prior to that, he put up an OPS of just .616 in Triple-A Columbus in 2001, even though his power — 11 home runs in 71 games — was still there to an extent. He repeated the level next year, and Baseball America even bumped him up to the No. 9 prospect in the game. But Henson only marginally improved with a .736 OPS in 128 games. The Yankees did give him a September call-up in '02, where he went 0-for-1 in three games as a pinch-hitter or pinch-runner.
The 2003 campaign saw Henson again return to Triple-A and fail to make meaningful progress. While the Yankees had been hoping for him to grab the bull by the horns and take the third base spot for himself, they gave up the hope that he would and traded for Aaron Boone at the deadline. I think we all remember what happened after that — though Henson at least got his first career hit in what would be his final career game: September 28, 2003.
Despite Boone infamously then injuring himself that winter, the Yankees were not prepared to give Henson a real shot at third, even before the megatrade for Alex Rodriguez. In February 2004, Henson left the Yankees' organization with the intention to return to football.
After focusing on baseball, Henson did not go remotely as high as he could've in the NFL Draft, but the Houston Texans had taken a flier on him with a sixth-round pick in the 2003 draft. However, the Dallas Cowboys and owner Jerry Jones had long been intrigued by Henson's potential, and they traded for his rights not long after Henson announced his return to football.
Henson would make sporadic appearances for them and a couple other teams over the next couple years, but he couldn't make the football thing stick either. Henson would spend a couple years in the Yankees' organization as a minor-league hitting coach, where he did work with the likes of a very young Aaron Judge. As of 2020, he was again trying to make the switch, having spent some time working with the Steelers and hoping to catch on somewhere as an NFL scout. Henson was inducted into the Michigan Sports Hall of Fame in 2021.
For the amount of talent he had in both, it's fairly remarkable that Drew Henson could not carve out a career in either baseball or football. Maybe regularly going back and forth hurt his chances for both sports, but other players have managed to do both to some degree of success. Maybe, he just didn't quite have enough to make it at the top level of either sport. Either way, Henson's ride was a wild one.
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