Drew Henson Went From Yankees Third Baseman to Dallas Cowboys Starting Quarterback

Originally a starting quarterback at Michigan, Drew Henson later defined the two-sport athlete. 

Think about how many kids growing up want to hit home runs for the New York Yankees or throw touchdown passes for the Dallas Cowboys. Considering how slim the chances of even making either league are, the odds of suiting up for both teams — outside of Deion Sanders — are even less.

Don’t tell that to Drew Henson. Within two years, Henson went from manning third base next to Derek Jeter on the Yankees to starting games at quarterback for the Cowboys. 

Drew Henson played third base for the New York Yankees

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Best known as Tom Brady’s successor at Michigan, Henson didn’t follow his former teammate into the NFL — at first.

Henson instead opted for a professional baseball career with the New York Yankees. A third-round pick of the Yankees in 1998, Henson signed a six-year, baseball-only contract worth $17 million with the team in March 2001.

The Yankees re-acquired Henson’s rights after trading him to the Cincinnati Reds in a package deal for reliever Denny Neagle.

Although the Yankees had Robin Ventura at third base in 2002, Henson made his debut during September call-ups. Henson played in three games that year and struck out in his lone plate appearance.

He also scored a run after pinch-running for designated hitter Jason Giambi. Henson went 1-for-8 across five games during the 2003 season.

The Yankees acquired Aaron Boone, now the team’s manager, to play third base. When the Yankees needed a new third baseman in February 2004 after Boone suffered a knee injury playing baseball, the team didn’t consider Henson.

At that point, Henson gave up on baseball and pivoted to football.

Henson later started at quarterback for the Dallas Cowboys

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Originally, the Houston Texans drafted Drew Henson in the sixth round of the 2003 NFL draft.

Houston later traded Henson to the Dallas Cowboys in the spring of 2004 for a third-round pick in the 2005 NFL draft. Houston used that pick on Oklahoma State running back Vernand Morency, who played two seasons with the Texans and another two for his hometown Dolphins.

Having given up on baseball, Henson joined the Cowboys for offseason workouts. Henson opened the 2004 season backing up Vinny Testaverde, the starting quarterback, and second-year reserve Tony Romo.

Henson went 6-for-6 for 47 yards and a touchdown in his NFL debut, a 30-10 loss to Ray Lewis and the Ravens. When Testaverde couldn’t play four days later because of an injury, Henson started against the Chicago Bears on Thanksgiving Day.

Henson only completed four of his 12 passes for 31 yards and an interception. Head coach Bill Parcells relieved Henson and threw Testaverde in at halftime.

However, because Henson started the game, he was credited as the winner in the Cowboys’ 21-7 victory.

Where is Drew Henson now?

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Drew Henson spent the rest of the 2004 season and all of 2005 on the bench. 

After stints in NFL Europe and with the Minnesota Vikings, Henson again saw playing time in 2008 on a Detroit Lions team that finished 0-16. Henson had a 20-yard pass, an incompletion, and two fumbles in a Week 13 loss to Kerry Collins and the Titans on Thanksgiving Day. 

Ten days later, Henson was sacked in a 20-16 loss to the Vikings. Detroit released Henson in April 2009, which marked the end of his professional sports career. 

Henson spent two years calling college football games, then rejoined the Yankees as a minor-league coach. He worked with future All-Star sluggers Aaron Judge and Gary Sánchez before becoming a scout.

Henson told the New York Post in April that he hopes to earn a job with an NFL team. He spent part of the Steelers’ 2019 training camp as an intern under Mike Tomlin.

Earlier this year, Henson worked with quarterbacks — including future first-round picks Justin Herbert and Jordan Love — at the Senior Bowl in Mobile, Ala.

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