Wolverine, Yankee, Cowboy: The Drew Henson Odyssey
Imagine standing under centre in The Big House, Michigan Stadium, bedecked in yellow and blue, 110,000 fans peering at you in expectation, living and dying with your every twitch.
Imagine receiving a Thanksgiving snap at Texas Stadium, the one with the hole in the roof so God could watch his favourite team, a blue star on your silver helmet, 65,000 diehards watching, dreaming, yearning.
Imagine striding to the plate at Yankee Stadium II, The House That Ruth Built, swathed in the famous pinstripes, 55,000 aficionados assessing your performance.
Imagine being teammates with Tom Brady, Derek Jeter and Tony Romo, Roger Clemens, Calvin Johnson and Mariano Rivera.
Imagine being coached by Larry Carr, Joe Torre and Bill Parcells.
Imagine being paid by George Steinbrenner and Jerry Jones.
Millions have harboured such aspirations.
Many have enacted them in the backyard.
A few have experienced one of these fantasies, playing for the Michigan Wolverines, Dallas Cowboys or New York Yankees.
But only one man has ever experienced the full gamut: Drew Henson, the 6-foot-5 quarterback-turned-slugger whose career encompassed three of the most iconic teams on earth.
This is a full retracing of his unique odyssey.
***
Drew Henson was born on 13 February 1980, in San Diego, California, the son of Carol, a physical education teacher, and Dan, a college football coach. The Hensons hopscotched across America, trailing the patriarch as he coached at San Jose State, Utah and Arizona State. When Dan took a job at Eastern Michigan, the family settled in Brighton, 45 miles from Detroit, where Drew became a three-sport star at the local high school. (1)
In three seasons of high school football, Henson completed 400 passes for 5,662 yards and 52 touchdowns – marks that rank second in the all-time Michigan high school annals. On the baseball diamond, Henson set national high school records for career home runs (70), RBI (290) and runs scored (259), while logging a 14-1 pitching record, and a 0.86 ERA with 174 strikeouts, as a flame-throwing senior. Named the 1998 high school baseball player of the year by USA Today, Baseball America and Gatorade, Henson also averaged 22 points per game in basketball and a 4.0 GPA in the classroom, honing a prodigious reputation. (1) (2)
Naturally, scouts and recruiters beat a path to Brighton High School, keen to catch a glimpse of its burgeoning unicorn. Every college in the country wanted Henson, who narrowed his football options to six: Stanford, Tennessee, USC, FSU, Michigan State, and Michigan. Concurrently, Dick Groch, an esteemed Yankees scout, trailed Henson, convinced he could become a big league pitcher within three years. (3) (4)
Groch famously discovered Derek Jeter, another Michigan prodigy, and practically begged the Yankees to draft the skinny shortstop out of Kalamazoo. Years later, even Jeter bought the Henson hype, as he called Drew in 1996 to recommend Casey Close as an agent. Henson heeded Derek’s advice and hired Close to field a slew of recruitment pitches. (5)
One such pitch came from Bo Schembechler, the legendary former coach of the Wolverines, who remained tethered to Michigan as an emeritus grandee. Schembechler, who also briefly served as president of the Detroit Tigers, told Henson to contemplate how badly he wanted to be the Wolverines’ quarterback. Henson obliged, and committed to Michigan the next day. (2)
That commitment did not deter the Yankees, however, and Groch arranged a Tampa baseball workout for the 18-year-old phenom. Mark Newman, the Yankees’ director of baseball operations, also travelled to Michigan to meet Henson, who told him, “I would rather hit a home run in the World Series for the Yankees than throw a touchdown in the Super Bowl.” George Steinbrenner, the Yankees’ win-at-all-costs owner, was characteristically enamoured with such a bold statement, and The Boss approved a gamble to select Henson in the 1998 MLB draft despite his football commitments. (3)
Following through, the Yankees picked Henson in the third round, 97th overall. “We’re selling, man,” said Brian Cashman, the team’s general manager, of subsequent attempts to lure Henson away from the gridiron. “Selling the major league experience and our tradition. We’d love for him to play only baseball, but if that’s unrealistic, we’ll try to help him decide to do both.” (6)
The pinstriped pitch included lunch with Steinbrenner, who was asked by Carol Henson about his satirical portrayal in Seinfeld. (7) Shortly thereafter, the Yankees gave Henson a $2 million signing bonus, with the promise of a further $2.7 million if he gave up football. (2) Drew demurred on the secondary bounty, but accepted the first, reiterating his desire to pursue dual paths as a Yankee and Wolverine. That made him a campus millionaire and placed a target on his back from the outset.
Henson reported to the Gulf Coast Yankees in the summer of 1998 and received his introduction to professional sports. In 10 games, the mountainous third baseman hit .316 with an .840 OPS. At that point, the media machine clicked into overdrive, unable to resist such a cartoonish fantasy. In an August 1998 edition of Sports Illustrated, Leigh Montville pondered whether Henson could break Roger Maris’ fabled Yankee single-season home run record, while quoting a Brighton High baseball coach who labelled Drew ‘the next Michael Jordan.’ (8)
Michigan coaches poured fuel on that fire when Henson reported for football training camp, comparing Drew to Jim Thorpe and John Elway – who, incidentally, was also drafted by the Yankees before starring with the Denver Broncos. (9) (10) “He is without question the most talented quarterback I have ever been around,” said Wolverines coach Larry Carr, while Henson’s arrival was greeted as ‘the second coming of Roger Staubach.’ (11) (12)
There was just one problem for the hometown hero: a skinny junior from northern California who had risen from seventh on the Michigan depth chart to become the starting quarterback. Tom Brady was his name, and Drew had previously encountered him at a summer camp run by his father. (2) Many Michigan fans clamoured for Henson to start, citing his local roots and intoxicating pedigree, but Brady excelled like a cyborg metronome, leaving Carr in a bind amid a brewing quarterback controversy.
“At a Michigan team autograph session, about 500 people lined up from midfield to the end zone to spend a fleeting moment with Henson,” wrote Ian O’Connor, “while the ignored Brady stood in the stadium tunnel with a student assistant named Jay Flannelly. Brady signed three autographs that day, tops, and never took his eyes off that endless line to Henson.” (13)
Many cite that moment as the genesis of Brady’s single-minded quest for sporting immortality – a ‘me against the world’ schtick putting a chip on his shoulder while sharpening his focus through a coldblooded prism. Understandably, Carr could not overlook such an epochal surfeit of motivated talent, so Brady remained the ostensible starter in 1998, with Henson getting into seven games as a backup.
A tricky situation brought out the worst in some. Drew’s father lobbied vociferously for his son to receive more playing time, and often appeared at Michigan practices. When Carr told Dan Henson not to come by, the helicopter parent parked on a nearby overpass and peered into the facility, studying his son’s game. (14)
Unperturbed, Brady led Michigan to a Citrus Bowl triumph over Arkansas, and Henson had a couple months off before reporting to Yankees spring training. Many students spent spring break in Florida, of course, but very few scrimmaged with Jeter, Rivera, Posada and Pettitte.
Henson subsequently spent the 1999 baseball season at High-A, with the Tampa Yankees, clubbing 13 homers in 69 games while posting a .280 batting average and a .345 OBP. Besotted with Henson’s potential, Newman, the Yankees’ minor league honcho, called Drew a ‘Jeter-type player’ while noting the ‘Ruthian, McGwire-esque’ bombs that left observers slack-jawed. (15) (16)
Come fall, such astonished glances were produced by tight downfield spirals, as Henson again dipped in and out of Wolverine action. In a tough spot, Carr trialled a makeshift rotation in 1999 that saw Henson and Brady split the first half of games, with the hot hand taking over in the second period. That plan was soon scotched, though, as the older Brady won out with remarkable consistency. (17) “I’m a student at the University of Michigan, and I’m a New York Yankee,” Henson philosophised. “How much more can a kid want?” (18)
Indeed, for Drew Henson, the idea was always to pick one sport in which to turn professional. Technically, the $2 million Yankee signing bonus made him a professional baseball player, but it was more an administrative formality to keep him in the organisation than a long-term commitment. A subsequent major league deal loomed, while college football’s fierce amateurism left Henson in a holding pattern. He would taste the best of both worlds before deciding his ultimate path.
When Brady was drafted 199th overall by the New England Patriots in the 2000 NFL draft, that path became a little clearer – for Henson, at least, if not for Cashman, Newman and the Yankees. With a glaring opportunity to start as the Wolverines’ quarterback, Henson was determined to play football during his senior year. Yankee executives grew frustrated and began to shop Henson in trade talks. The Cubs sent a scout to watch Henson in Double-A amid rumours of a deal sending Sammy Sosa to New York, before Cashman dealt Drew to Cincinnati with two other prospects in return for Denny Neagle. (19)
Henson was actually hitting well at Double-A at the time of the trade, with seven homers and a .287 average in 59 games. He did not perform well in the Reds system, however, with a foot injury contributing to a measly .172 average in 16 games to round out 2000.
That foot injury kept Henson off the gridiron, too, for the Wolverines’ first three games. Upon returning, though, Henson played the best football of his collegiate career, tossing 16 touchdown passes in eight games while steering Michigan to a famous victory over traditional rivals Ohio State and, ultimately, a share of the Big Ten championship.
Most NFL draftniks pencilled Henson atop their nascent big boards for the 2002 draft, while the Michigan quarterback became a consensus favourite for the Heisman Trophy in his senior year. An NFL future seemed increasingly likely, with the expansion Houston Texans interested in selecting Henson first overall. As such, Henson told the Reds they only had a ‘20% chance’ of signing him to an extension due to their perceived financial limitations compared to their NFL counterparts, clarifying the situation further. (20)
The Yankees never stopped loving Drew Henson, though, and Cashman fancied one last crack at selling the pinstriped dream before he finished up at Michigan and became the first quarterback in Texans history. Perhaps encouraged by subterranean chatter, in March 2001, the Yankees traded Wily Mo Pena – a bonafide prospect in his own right – to Cincinnati for Henson and Michael Coleman. “Our intent is to convince him to play baseball,” said Cashman. “That’s always been our intent since we drafted him.” (20)
As time wore on, indeed, Henson’s desires narrowed: he either wanted to play in the NFL, or become a Yankee. Only the mystique and aura of sports’ most powerful juggernaut could lure Henson from the gridiron – to hell with your humdrum Cincinnati or dreary Kansas City. It was pinstripes or shoulder pads, and 2001 figured to be a determinative crossroads in that conundrum.
Within four days of reacquiring Henson, however, the Yankees paid a whole heap of cash to make that problem go away. Building on previous failed offers, the Yankees blew Henson away, offering the 21-year-old a six-year, $17 million, baseball-only contract. Sensing a final chance to realise his Bronx dream, Henson accepted the offer and left Michigan before his senior year began. “To me, there would be no greater goal than to help win a World Series for the New York Yankees,” he told reporters after making a life-changing decision. “I will keep memories of the University of Michigan close to my heart.” (21)
For his part, Cashman was ecstatic, crowing that ‘we got back at the NFL for taking Elway away from us.’ (21) Yet almost immediately, conspiracy theorists claimed Steinbrenner – an Ohio State alum and donor – overpaid for Henson to leave Michigan without a quarterback. (22) That Henson-led defeat to the Wolverines stung Buckeye fans, to the point where Henson was booed during games at Triple-A Columbus, in Ohio, despite playing for the hometown team. He also received hate mail, creating a difficult environment in which to develop. (23)
To wit, Henson struggled throughout the 2001 season, his first as a baseball-exclusive athlete. The Yankees assigned two-time World Series champion Clete Boyer to personally tutor Henson at Triple-A, where he logged a .222 average and .249 OBP with 11 home runs in 71 games. (24) Baseball America was still bullish on Henson’s prospect rating – Allan Simpson ranking him 22nd, ahead of Albert Pujols, Adam Dunn, Jimmy Rollins and Carl Crawford; and Will Lingo placing him fifth, ahead of Ichiro Suzuki, CC Sabathia, Roy Oswalt and Miguel Cabrera (25) – but the first glimmer of doubt began to percolate among Yankee decision-makers.
Henson improved in 2002, benefitting from 128 games at Triple-A and earning hyperbolic comparisons to Mike Schmidt. (26) While 151 strikeouts subdued a .240 average and .301 OBP, Henson clubbed 18 homers and 30 doubles. When major league rosters expanded in September 2002, the Yankees promoted Henson for a cup of coffee – more to observe and learn by osmosis than contribute to a 103-win, division-wining juggernaut.
Nevertheless, vaunted Yankee manager Joe Torre put Henson into three games – as a pinch-runner for Bernie Williams and Jason Giambi, and as a pinch-hitter for Robin Ventura. Henson struck out against Dámaso Marte in that lone plate appearance, late in an 8-1 loss to the White Sox, but learned a lot from his dynastic colleagues, regardless.
Meanwhile, despite taking David Carr first overall in the 2002 NFL draft, the Texans took a flier on Henson in the sixth round a year later, selecting the Yankee 192nd overall. There was no suggestion that Henson hankered for a football return, but Houston reserved his NFL rights anyhow, hedging on any future change of heart.
Seemingly unmoved, Henson spent another full season at Triple-A in 2003, cracking 40 doubles and 14 homers while contributing 78 RBI in 133 games. Alas, a lack of plate discipline dogged Henson, whose seasonal OBP slipped to .291, saddled by an ominous 3.8 strikeout-to-walk ratio. Warning lights flashed on the dashboard in Yankee command, poor underlying metrics casting doubt on their top prospect.
Still, Cashman again promoted Henson to the big leagues in September 2003 – this time for more than three weeks, with a locker next to pitching behemoth Roger Clemens. (2) Henson got into five games as the Yankees successfully defended their AL East crown, with sporadic plate appearances against the Red Sox, White Sox and Orioles doing little to convince of an impending breakout.
Nevertheless, on the season’s final day – 28 September, 2003 – Henson chopped a ball up the middle off Baltimore’s Eric DuBose. In fairness, José Morban, the Orioles’ shortstop, should have made a play on the bounding ball, but it evaded his lunging grasp and trickled into left-centre field for a base hit – the first, and ultimately the last, of Henson’s major league career.
To that end, the Yankees sought third base reinforcements at the 2003 trade deadline, frustrated by Henson’s .679 OPS in 1,339 Triple-A plate appearances. Acquired from Cincinnati, solid veteran Aaron Boone made the hot corner his own, and a sense of foreboding coloured Henson’s predicament when Boone hit a famous pennant-clinching, walk-off home run against the hated Red Sox in Game 7 of the ALCS. New York lost the subsequent World Series, but it seemed unlikely that Henson would dislodge the newfound hero in 2004.
Even when Boone injured himself in an offseason basketball game, tearing an anterior cruciate ligament then watching the Yankees tear up his contract, Henson was overlooked as a potential replacement. Miguel Cairo and Enrique Wilson were prioritised as internal replacement candidates, as Henson’s hopes of a pinstriped future dwindled to dust.
Receiving the message loud and clear, Henson announced his baseball retirement on 3 February, 2004, foregoing the remaining three years and $12 million on his Yankees contract to pursue NFL opportunities. Less than two weeks later, the Yankees sent Alfonso Soriano and Joaquín Arias to Texas for Alex Rodriguez, the game’s most prodigious star, who agreed to play third base for New York, in deference to Jeter. (2)
At 24, meanwhile, Henson faced a far more uncertain future. The Texans held his NFL rights, but Carr was firmly ensconced as Houston’s starting quarterback – so much so, general manager Charley Casserly publicly shopped Henson and worked to facilitate a mutually beneficial trade. A hastily arranged showcase drew 21 NFL teams, and five – Buffalo, Cleveland, Dallas, Green Bay and Miami – expressed genuine interest in a deal. (27)
Ever the showman, Cowboys owner Jerry Jones had a penchant for such attention-grabbing reclamation projects. In fact, the Cowboys already had two former baseball players – Quincy Carter and Chad Hutchinson – cosplaying as quarterbacks, to little effect. Naturally, Jones wanted Henson in blue, white and silver, despite the three-year gap on his football resume. Jerry pressed his functionaries to clinch a deal, and Dallas sent its third round pick in the 2005 draft to Houston for Henson, who received an eight-year, $3.5 million guaranteed contract. (28)
However, as always seemed to be the case for Henson, an emerging superstar blocked his path to self-actualisation. First, it was Brady. Then – in retrospect, if not in reality – it was A-Rod. And in Dallas? Well, a young Tony Romo was finding his feet as the Cowboys’ next franchise quarterback, enriching the fine lineage connecting Troy Aikman, Staubach and Don Meredith. And in another quirk of fate, Romo had, like Brady, worked with Dan Henson at summer instructional camps, honing skills that became roadblocks to his son’s success. (2)
In truth, however, Bill Parcells never really took to Drew Henson. A feted coach playing out the string in Dallas, Parcells often chafed at Jones’ razzle-dazzle schemes, which generated tabloid headlines more efficiently than NFL wins. A hard-nosed football lifer, Parcells seemed personally offended by Henson’s past preference of cowhide over pig skin, and Drew received limited opportunities to quarterback America’s Team.
Ironically, when he did enter the fray, Henson performed well for Dallas. Debuting against Baltimore in the fourth quarter of a lopsided loss on 21 November, 2004, Henson went 6-for-6 and threw a 1-yard touchdown pass to Jeff Robinson. Henson did start four days later, in the Cowboys’ traditional Thanksgiving game, against the Bears, before 64,026 at Texas Stadium, but a big interception served as confirmation bias for Parcells, who pulled the former Wolverine in favour of Vinny Testaverde. Bizarrely, Henson never played for the Cowboys again, and Dallas cut him in August 2006 after an NFL Europe stint with the Rhein Fire.
From there, no longer a prized prospect, but rather a cautionary tale, Henson caught on with the Vikings’ practice squad. He never saw game action for Minnesota, and washed up with the 0-16 Detroit Lions in 2008 as a 28-year-old ‘bust.’ A transient teammate of Dan Campbell and Calvin Johnson on his hometown team, Henson registered two passing attempts late in a 47-10 drubbing by Tennessee, but was subsequently released when Detroit drafted Matthew Stafford first overall in April 2009.
And with that, a can’t-miss, three-sport phenom retired, for good, before his 30th birthday. After riding a relentless rollercoaster for a decade-plus, Henson took some time to travel and decompress, visiting China, Thailand and Spain with his wife. (7) He worked with psychiatrists and therapists to flush the frustration of unrealised greatness, and called college football games for ESPN. (29)
Between 2012 and 2017, Henson returned to the Yankees as a scout and minor league hitting instructor, working with a young Aaron Judge, before interning with Mike Tomlin and the Pittsburgh Steelers in 2019. (2) Tomlin was defensive coordinator with the Vikings when Henson passed through, and the two maintained a relationship. An NFL coaching career never materialised for Henson, though, as his divergent instincts led to various entrepreneurial ventures, including stakes in a boat charter business and a money management firm. (29)
Michigan voted Henson into its baseball hall of fame in 2020, and he received his day in the sun a year later due to Covid-19 restrictions. By that point, Tom Brady had seven Super Bowl rings and was about to enter the penultimate season of a glittering 23-year NFL career. Cashman was still Yankees GM, with five championship rings of his own. Meanwhile, Henson lurked in suspended potentiality – an unshakeable caveat attached to his story, an unwanted asterisk next to his name.
***
The common synopsis portrays Drew Henson as a gargantuan bust, with perhaps the most unfulfilled potential in modern sports history. “The greatest athlete that never was,” concluded Joel Sherman. “Drew Henson couldn’t miss in two sports – yet he did.” (2)
Undoubtedly, Henson is a great ‘what if’ of contemporary sports, whose butterfly effect strains credulity. If he bloomed into an elite professional quarterback, there may be no Brady-Belichick dynasty in New England. If he panned out as a slugging third baseman, there may be no A-Rod in pinstripes, and no Boone in the Yankee dugout. And if he enacted the grandiose hallucinations of Jerry Jones, there may be no Super Bowl drought in Dallas.
However, any notion of Drew Henson ‘failing’ is relative to the context of the expectations placed upon him – by scouts, coaches, fans, reporters and even his own father. Sure, Henson fell short of those expectations, but in a conventional setting – in the realm of mere humans – he can also be viewed as astonishingly successful.
If failure is playing for the Michigan Wolverines, New York Yankees and Dallas Cowboys, sign me up.
If failure is taking playing time from the greatest quarterback who ever lived, God help the rest of us.
And if failure is telling your children about the time you collected an MLB hit and an NFL touchdown pass, we need to recalibrate our standards.
Yes, in one sense, Drew Henson only logged one hit and one touchdown pass. But also, in another sense, Drew Henson logged one hit and one touchdown pass! That is an amazing accomplishment, and a glass half-full reading cites Henson as one of the most phenomenal athletes to lace a pair of cleats.
Of course, we can compare Brady’s seven Super Bowl wins to Henson’s barren stat sheet, but that is unfair. Besides, Drew has always been very self-deprecating and gracious regarding his former teammate. We should show the guy more respect, quite frankly, because he achieved incredible things while grappling with unbelievably tough choices at a delicately young age.
Before turning 20, Henson was likened to Jim Thorpe, Michael Jordan, John Elway, Roger Maris, Roger Staubach and Mike Schmidt. He embarked on a whirlwind journey featuring Brady and Jeter, A-Rod and Romo, Stafford and Judge. Schembechler and Steinbrenner fought for his signature over dinner. Torre and Parcells pencilled his name into lineups. Jones and Cashman dreamed on his potential. And through it all, the kid remained humble, never putting a foot wrong while carrying himself with grace.
An argument can even be made that Drew Henson never received a fair shake. His final MLB game came at age 23, whereas Judge debuted with the Yankees aged 24. Henson was a raw power hitter who lacked plate discipline, and reps would have been essential to him unlocking consistency. He never got those reps, and constantly played catch-up while spreading himself thin. Likewise, in Dallas, Henson did enough to earn further looks, but Parcells’ stubborn reluctance to grant such opportunities expedited an exit.
Alas, in hindsight, it was not meant to be, but Drew Henson should not be synonymous with untapped promise. This, after all, was a guy signed by three of the most powerful sporting institutions in the world. A guy caught between two major loves, who could not commit to one. A polarising polymath, whose like we will never see again.
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