Drew Henson, the greatest athlete that never was, has a new sports dream
He was the greatest athlete that never was.
Drew Henson couldn’t miss in two sports — yet he did.
“I didn’t have the success for which I hoped or expected,” Henson told The Post in a recent interview, “but I have this wealth of life experiences.”
Does he ever. He is a sports Zelig — experiencing brushes with greatness over and over, though never getting there himself.
He ties Tom Brady to Derek Jeter more closely than a mansion on Tampa’s Davis Islands does. He played for Joe Torre, George Steinbrenner and the Yankees, and he played for Bill Parcells, Jerry Jones and the Cowboys.
He — not Jeter — is arguably the greatest schoolboy baseball player ever produced by the state of Michigan.
He — not Brady — is the last University of Michigan quarterback to beat Ohio State in Columbus.
Yet an athlete once compared to Mike Schmidt in one sport and to John Elway in another totaled one major league hit and one NFL touchdown pass. His failure at third base led to Aaron Boone, and then Alex Rodriguez, for the Yankees. His failure at quarterback led to Tony Romo’s rise for the Cowboys.
Henson signed his first pro contract with a baseball dynasty and finished with an 0-16 NFL team — the 2008 Lions. Detroit then drafted Matthew Stafford with the first-overall pick in 2009 and immediately waived Henson.
This being Drew Henson, though, his wife just happened to have gone to the same Dallas high school as Stafford, her brothers attended school with Stafford, and Henson himself just happened to be a Cowboy, so he sat in the stands with Stafford’s father and watched him in high school.
Of course, he did.
When Henson was in high school, he was convinced to go to Michigan by legendary Wolverines football coach Bo Schembechler. He also was cold-called by Jeter to recommend an agent — call-waiting clicked in while Henson was on the phone with a friend. Somehow Henson ended up living next door to A-Rod when he was on the way out from the Yankees and A-Rod was on the way in. And, of course, when Brady finally left the Patriots, he wound up on the Buccaneers, moving into Jeter’s place on Davis Islands — which is a short drive from South Tampa, where a 40-year-old ex-third baseman/ex-quarterback lives.
“And my story is not done,” Henson said.
Henson has a wife, Madeleine, and 7-year-old daughter, Perry, who goes to the same private school as the children of Bucs GM Jason Licht, though the coronavirus pandemic has the Hensons home-schooling Perry. And Henson’s hopscotch life has him eyeing football again.
After playing, there were two years at ESPN calling ACC college football games, then six years back with the Yankees, first as a minor league hitting coach who logged some instructional league time with Aaron Judge and Gary Sanchez, and then as a scout.
Last August, he served two weeks as a coaching intern with the Steelers — Mike Tomlin was the defensive coordinator with the Vikings during Henson’s cup of coffee there (really, he crisscrosses with so many notables) — and in January he was a group leader for quarterbacks such as Justin Herbert and Jordan Love at the Senior Bowl in Mobile, Ala., helping to guide practices and writing scouting reports for NFL teams.
He is hoping to join an NFL team as a scout now because — he believes — a life full of Schembechler and Steinbrenner, Jones and Torre, Playboy All-America-status and 0-16 Lions has taught him what the predicted greatness could not. About the best and worst leadership. About huge expectations and bigger downfalls. About the need for patience and fortitude and trusting yourself.
“So, I don’t have Pro Bowls and I don’t have All-Star Games, but I have this wealth of experience and can use it to help a team for the next 20 or 30 years,” Henson said. “Because I have lived these. And for scouting, I can use myself as an example and all the people I have been around.”
Henson has always been around football. His father was a college coach. When Dan Henson was quarterbacks coach at Arizona State, he recruited a kid named Tom Brady. Before his high school senior year, Brady went to a summer football camp that Dan helped run, and there was a ninth grader there. Yep, Drew.
That was the first time the quarterbacks met. Brady went to Michigan, and shortly after that, Dan Henson got a job at Eastern Michigan and moved the family there.
At Brighton High School, Drew Henson averaged 22 points a game and was All-State in basketball. He was rated the country’s top high school quarterback while also being a defensive back and USA Today’s All-American punter. On the baseball field, he set high school career records with 70 homers and 290 RBIs. Oh yeah, he also threw 95 mph as a pitcher, whiffed 20 of 21 in one game and was the consensus national player of the year as a senior (this March he was named to the Michigan Baseball Hall of Fame).
He really was a can’t-miss prospect.
As a high school junior, Henson was torn between Michigan and Florida State, loving the Seminoles because he so admired offensive coordinator Mark Richt, who (of course) went on to be Stafford’s head coach at Georgia.
“I was 15 and Bo [Schembechler, then with an emeritus role at Michigan] sat me down in his office one day and he said, ‘Drew, you are going to have to decide one thing,’ ” Henson recalled. “He knew I was good. He asked me if I knew he had been president of the Tigers. I was like, ‘Yes, Bo, I know.’ He wanted me to know he had a baseball background, too. He told me I had to decide how badly I wanted to be the Michigan quarterback. And then I committed the next day.”
The commitment was powerful. Henson told Michigan coach Lloyd Carr that no matter what happened in the June 1998 baseball draft, he wanted the college experience and was coming to play quarterback for the Wolverines. Henson would have been a top baseball pick without that. Instead, the Yankees took a gamble in the third round and gave Henson a $2 million bonus with a promise of another $2.7 million if he gave up football.
Carr had just guided an undefeated national championship team in 1997 with Brian Griese at quarterback — after he beat out Brady, among others. In 1998, there was no returning starter. But Brady as a red-shirt junior won the job, though Henson played in nine games.
The following year, Carr installed a controversial plan: Brady would quarterback the first quarter, Henson the second, and whoever played the best would play the second half. Perhaps Carr was feeling the pressure that if Henson didn’t play, he would jump full-time to the Yankees. After all, at 19 he had just hit 13 homers in only 254 at-bats at High-A before returning for his sophomore season.
With three games left, Carr decided to go with Brady, who won out, including a 35-34 overtime Orange Bowl win over Alabama in which he threw for 369 yards and four touchdowns and ran for another.
“What people fail to understand is there is competition at every position all the time,” Henson said. “And at Michigan they preach the competition. It is what develops good culture, a great team and great leadership. You walk in and want to get on the field.
“At the same time, you walk into a quarterback room that is close knit. Tom is three years older. I am looking up to him. You learn from the older players, like you do on every team. Preparation, film study, just overall knowledge of the game. From that aspect, I was learning from him. Yet, on the field you are competing for reps.
“Obviously, it is something that everyone is talking about, but you know what is going on inside. You control what you can control. You control how you prepare. You support your teammates. And then whoever they go with that is the deal, that is the way sports is.
“He was always good to me, and we got along really well. There was nothing negative about it other than the fact that you had two quarterbacks who are alternating. But everything worked itself out and certainly made me better.”
Henson said the relationship with Brady was never problematic and that when the two saw each other over the years it was always cordial, but the two haven’t spoken in years. Now that Brady is in Tampa, though, Henson said, “I hope we can go for lunch.”
Brady famously lasted until the sixth round and the 199th pick of the 2000 NFL Draft. His exit left Henson as Michigan’s starter. But first Steinbrenner made a lucrative offer for Henson to forgo his junior year and come to a franchise that had just won three of the past four World Series. Steinbrenner, once a football coach, had a fascination with the sport and once drafted Elway and tried to talk him out of an NFL career to play right field for the Yanks.
Henson turned down Steinbrenner’s pitch to Casey Close (yes, Henson did pick Jeter’s agent) to make “Drew a Yankee for life.” So the Yankees, trying to win a third straight title and needing a starting pitcher, traded Henson in a July deadline package to the Reds for Denny Neagle. Henson played 16 games with Double-A Chattanooga, then returned to Ann Arbor.
Henson, though, broke his foot and missed the first three games of his junior season, but came back to beat Ohio State (yep, the last time the Wolverines won in Columbus) and beat Auburn in the Citrus Bowl. And now came the biggest decision of his life. He could:
1) Leave for the 2001 NFL Draft. Henson said he saw his scouting grade and it was the same as that year’s No. 1 pick, Michael Vick. But Henson felt he simply did not have enough snaps as a starter to make the jump yet.
2) Return for his senior season. Henson, however, was losing his best receiver (David Terrell) and four offensive linemen (including stars Jeff Backus and Steve Hutchinson) and was concerned his performance would suffer and his NFL stock would drop.
3) Heed Steinbrenner’s siren call. The Yankees let the Henson camp know they could reacquire him from Cincinnati and fast-track him to the majors, but only if he would throw away football for good.
“Those are the three things I am trying to balance at 20 years old,” Henson said. “Plus, there was this:
“I am going on my third year of having no time off. Literally, spring practice one day, spring break, fly to Tampa, do eight days of spring training, fly back to Ann Arbor. Compete with Tom in spring ball. Finish classes. Fly back to Tampa. Play for three months. Have a week off before you begin training camp.
“My body was breaking down both mentally and physically. I didn’t know if I could do another 12 months of this constant back and forth. And that sped up the timeline of making a decision. After my junior year, hey, 12 months [a year], I am freaking tired now. I’m exhausted mentally and physically and I feel I have to make a decision now.”
In March 2001, having played 159 minor league games — none above Double-A — Henson agreed to a six-year, $17 million deal to give up football permanently. The Yankees hoped he would replace Scott Brosius at third base as soon as 2002. In a statement at the time, Henson called baseball “my passion.”
After so many years of being told he was going to have to choose one sport over another, Henson finally did. At least that is what he thought.
“It is like telling a 20-year-old kid, who has two things he loves to do, ‘Hey, you have to give up one, and you will never, ever do it again.’ And you might be the best kid in the country doing it,” Henson said. “That is a really hard thing to do. It isn’t like picking a sport. It is like retiring from the other. And that is a difficult concept to grasp.”
In football, more preparation — film study, practice, meetings — helped him. In baseball, Henson found himself overthinking every swing and miss. And one item he returns to over and over in conversation is that he learned patience too late in life. He so badly wanted to get to New York that he didn’t appreciate how little high-level baseball he had played and how much couldn’t be speed-experienced.
There was another problem. The Yankees’ Triple-A affiliate was still in Columbus, Ohio. So for three years — despite being a “home” player — the last Michigan quarterback to win in Columbus was booed during every at-bat at Cooper Stadium.
It all played on Henson — the impatience, the jeers. He didn’t replace Brosius, and by 2003 it was clear he was not close to playing next to Jeter, who had become a mentor. Plus, he was bored. The ball only came to him a few times a game, and there were just four at-bats. The Yankees traded for Boone in July 2003, and he was under control through 2004. That also was a scream to Henson.
“You have a lot of third basemen who hit homers and play good D. I think I am one of them,” Henson said. “But my quarterback skill set, I felt with all my tools, was higher than my baseball. We are splitting hairs here. I love doing both. But those are all things that went through my mind. And you only get one life. I was 23. And I could have continued playing baseball for another couple of years and the football is gone.”
Henson believes if he would have played his senior season, he would have settled on football plus he, not David Carr, would have been the No. 1-overall pick in 2002 by the Texans. Instead, the Texans took him the following year, and like Brady, he was now a sixth-rounder.
Henson had $12 million left on his Yankees contract. But he began working out as a quarterback, and on his 24th birthday, Feb. 13, 2004, the Texans, knowing they were planning to trade Henson, had an audition watched by 21 teams plus a Houston resident named Roger Clemens — next to whom Henson lockered in The Bronx during his brief Yankees tenure.
Three days later, the Yankees traded with the Rangers to obtain Alex Rodriguez to replace Boone, who had been released after blowing out his knee playing basketball, but not before hitting the ALCS Game 7-clinching homer versus the Red Sox. If Henson had succeeded in MLB, there would have been no Boone trade and homer, and probably no Boone as Yankees manager.
Rodriguez had been traded from Dallas to New York, while Henson was leaving New York to play with Dallas — he and A-Rod were next-door neighbors briefly in Harbor Island. The Cowboys traded a 2005 third-round pick to the Texans for Henson, who signed an eight-year contract at minimum salary each year (with a chance to make considerably more in roster bonuses).
The trade was engineered by Jones. But Parcells was the coach. He had his old Jets quarterback, Vinny Testaverde, and Parcells and his quarterbacks coach really liked an undrafted signee. The quarterbacks coach was Sean Payton. The undrafted signee was Romo. The tension between what Jones wanted and what Parcells wanted was real.
Henson was rusty after having been away from quarterbacking for a long time. He got just one start, his only one in the NFL, on Thanksgiving 2004 against the Bears. He led a TD drive but threw a pick-six, and Parcells benched him at halftime for Testaverde.
“I got to start a game, I threw a pick, [Parcells] pulled me, everyone knows the story,” Henson said. “Here is what I think and what I pretty much know: Jerry Jones is a gambler. He will take chances. And Parcells had found Tony and signed Tony.
“Tony should have been drafted. I trained with Tony at IMG before the draft. My father worked with Tony in college in summers. I knew Tony even before he got to Dallas. There are a lot of strange connections. Bill found Tony and signed Tony. And Jerry pushed to trade for me. So there is that dynamic. And I don’t think Coach Parcells liked me from the beginning for whatever reason. I had never had a problem with a coach. But looking back, clearly, he didn’t like me. So Jerry was always great for me. It worked out how it worked out. Parcells went with his guy. Tony turned out to be a really good play. And they won one playoff game. Make of it what you want.”
Henson doesn’t regret his time in Dallas — it is where he met his wife. That was followed by short stints with the Vikings and Lions, and then, at 29, he was done.
“I am [at peace why he didn’t make it in either sport],” Henson said. “You do go through, ‘Why am I 29 years old and not playing any longer?’ One thing about my personality is wanting to know everything — I consider myself a bright guy — and continuing things as long as I can. I took the two sports one step farther than I should have, where your natural talent isn’t different from anyone else’s and maybe they have more experience than you. You are playing catch-up in that regard.
“I was a part-time baseball player moving up the minor league ranks at an accelerated pace that, by 21, I was at Triple-A with barely a full season of at-bats. But to me it didn’t matter. I was trying to get to the big leagues the next day and be an All-Star at 21.
“So, me understanding the progression of my development and realistic expectations that were not anywhere near the expectations in my own mind, that part of it, I just needed more patience. Every step along the way, I felt I made the right decision with the information that I had. But what I lacked was being patient and letting the process play out. I learned that as I got older. …. I’m as competitive as I have always been. But when you go back through it, yeah, I would never have thought I would fail to accomplish what I did. Again, that’s life. And I am a lot tougher because of it.”
Even now, though, you hear the pull in both directions. Henson thinks if he had concentrated on football he would have succeeded, and he thinks his skills would have turned out similar to those of Kris Bryant if he had just focused on baseball.
“I’ve been asked the question a million times: What is your favorite thing?” Henson said. “I would say I love hitting a baseball more than anything, but there is nothing like playing quarterback. And having the ball in your hands. And being at that position.”
So he has gravitated back to football. He believes he was close to a job with an NFL team when the pandemic hit, and he has been asked to wait. A lifetime of experience has finally afforded him what he specifically lacked in baseball.
“Finally,” Henson said, “I learned, like even now with the virus, patience and that not everything happens on my timetable.”
So the guy who couldn’t miss, but did in two sports, waits — patiently — to be allowed back into the game.
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