Once Ticketed for 2-Sport Superstardom, Drew Henson Travels New Big League Path

Scott Miller@@ScottMillerBblNational MLB ColumnistJune 8, 2015

B/R via Getty, AP Images

Drew Henson is on the run. Sure, he's been flushed out of the pocket before, plenty of times. But never quite like this.

The plan was to drive to Rome, Georgia, last week. Then he was diverted to the Dominican Republic. And now he is back, clearing customs, a brief stop home and then back to see more prospects in the Single-A Florida State League.

Where scrambling once meant eluding defensive linemen from Ohio State and the Minnesota Vikings, now the word has taken on an entirely new meaning for Henson. And he loves it.

"I really like scouting," he says. "It's different because, instead of the coaching side where you're trying to help guys improve, you're evaluating. It's a different mindset.

"I'm evaluating pitchers and catchers and learning a lot, because I played third base and have never broken down some of these mechanics.

"So it's been a cool two months."

It is early June, which means it is time for another major league draft, which means, wherever Henson is and whatever he's doing, it is both a nostalgic and bittersweet time of year. Forget, for a moment, these cool past two months. Henson, 35, has packed a lifetime of learning—and scrambling—into the past six years.

The New York Yankees' third-round pick in the 1998 draft after a stellar high school career for Brighton (Michigan) High School, during which he crushed a then-schoolboy record 70 home runs, talent evaluators at the time practically had a spot carved out for his plaque in Monument Park.

But, wait. Also a quarterback for the University of Michigan, Henson split time with legend-in-the-making Tom Brady in 1999 before taking the Wolverines' starting job upon Brady's departure for the NFL. Henson was the Houston Texans' sixth-round pick in the 2003 NFL draft.

The next Bo Jackson? Deion Sanders?

Not so much.

Not every draft story ends with standing ovations and retired numbers.

Dallas Cowboys  quarterback Drew Henson  releases a warm-up pass before play  against the Philadelphia Eagles November 14, 2005 at Lincoln Financial Field in Philadelphia.  The Cowboys defeated the Eagles 21 - 20.  (Photo by Al Messerschmidt/Getty Images)
Al Messerschmidt/Getty Images

Henson wound up living the dream of every baseball-saturated little boy by wearing Yankees pinstripes…for eight whole games.

He also lived the dream of every football-crazy kid by playing in the NFL, first for Dallas and then Detroit. He even started a sacred Thanksgiving Day game for the Cowboys. His NFL ledger: nine games, one start, one touchdown pass.

But by 2009, at 29, he was finished with both sports. A has-been. In many eyes, a never-was.

"You come around and say, 'OK, I'm 30 years old, what am I going to do for my next career?'" Henson says. "What am I going to put my energy into?"

On this Saturday afternoon, his wife, Madeleine, is at the grocery store and their daughter, Perry Flynn, 2, is running around the house, showing off for dad. Dad? His itinerary is laid out clearly in front of him: lunch for Perry Flynn, knock off a few things around the house before packing his suitcase again, the rescheduled trip to Rome next week.

From his football days, he knows: The clock is always ticking.

From his baseball days, something else: Life is nothing more than a series of adjustments.

Drew Henson

So Henson rolls out, always searching downfield, innately knowing to double-check the signs while he's moving.

Time was, the scouts were watching him.   

Now, he settles in with the scouts to watch the prospects.

He reunited with the Yankees in the fall of 2012, after hanging up his cleats for good, smack at the beginning of the chapter entitled, What Am I Going to Do With the Rest of My Life? He spoke with Mark Newman, the Yankees' senior vice president of baseball operations from 2002 to 2014, and the club happened to have an opening for a hitting coach at the rookie-level Gulf Coast League. Maybe we can see if there's a fit, they figured.

That lasted through the 2014 season, when a pro scouting job opened. Maybe let's try this, get some experience, see how things go and learn another part of the game, they figured.

"I've always been intrigued by how you put together a team," Henson says. "Being in the Dominican Republic, evaluating 16-year-olds, doing spring training scouting as Billy and Cash are trying to finalize the roster. I find it very interesting."

Cash is Brian Cashman, the Yankees' general manager since 1998. Billy is Billy Eppler, Cashman's right-hand man and the Yankees' director of pro scouting.

"It's not like the NFL, where you sign a guy to help your 53-man roster, and if it doesn't work out, you move on," Henson says. "Here, you try to project."

So, no, this is not quite how Henson once envisioned his career with the Yankees would go.


KATHY WILLENS/Associated Press

He was signed out of high school by Dick Groch, the scout made famous by landing another Michigan schoolboy. Derek Jeter.

"I'd met him after ninth grade, playing ball in Michigan," Henson says of Groch. "Anytime you meet a scout from the Yankees, it perks you up."

The next two or three years, Groch was around all the time. By his senior year, Henson had something else in common with Jeter: an agent, Casey Close. Talk about a promising future.

Toru Takahashi/Associated Press

"In 12th grade, I was on the phone with a friend, and this was before caller ID, when the call-waiting beeped," Henson says. "I clicked over, and it was Derek Jeter. I told my friend, 'I've got to take this.'

"So Derek says, 'Hey, how ya doing, best of luck. I just want to endorse Casey.'"

Not long after, Henson's minor league career was underway and he was at Jeter's house near the Yankees' complex in Tampa, Florida, for dinner, along with other young Yankees.

"He was always around, always accessible for the young guys," Henson says of Jeter. "Because when he was a young player, Don Mattingly and some other veterans treated him that way. It was stuff he took from them.

"That's why you're a captain."

Being a Yankee was perfect, for many reasons. Among them: The Yanks were the only MLB organization who told him out of high school that they would work with him so he could play two sports.

So in the summers, he was a baseball player. A Yankee.

Then, around Aug. 1, they released him from whichever farm team that was developing him—Single-A Tampa, Double-A Norwich and Chattanooga—and he would return to Ann Arbor, Michigan.

From then through the spring, he was a student and a football player.

It was during the 1999 season, when Henson was a freshman and Brady was a fifth-year senior, that they split time at quarterback. That ought to tell you straightaway how good a football player Henson was. The Tom Brady? Splitting time with a freshman when he was a fourth-year junior?

CARLOS OSORIO/Associated Press

"He and I were the only guys who understood, going through a situation like that, that that was not the way the position was meant to be played," Henson says. "Coach [Lloyd] Carr told us he knew it wasn't fair to either of us, but we both deserved to play."

For many years, they kept in touch. Now, Henson says, it's been "four or five years" since he's spoken with Brady.

"I learned a ton from him," Henson says. "I pull for him.

"He made me better, and I hope I made him better. I knew he was smart, and the success he's had doesn't surprise me."

Summers during that time, Henson's baseball career didn't exactly take off. He moved through the lower levels of New York's system fairly smoothly, landing in Triple-A Columbus in 2001, when he was just 21.

It was there that things stalled. Though he walloped 70 doubles over the 2002 and '03 seasons, he didn't hit over .240. In '03, his on-base percentage dropped to .291. The Yankees called him up in September 2002, and he got into three games. They called him up a year later, and he got into five games. Big league totals: 1-for-9 (a single), three strikeouts.

There were a few significant issues.

Given his supreme talent in two sports, Henson never gave himself a fair chance by putting in the time required, especially in baseball. And the Yankees, looking for a return on their investment, rushed him through their system. It was a lethal combination.

And while all of that was happening, there was one thing about being a Yankee that was far from perfect: Their Triple-A team was located in Columbus, Ohio. Home of Ohio State University.

One of the many, many reasons Michigan hired superstar coach Jim Harbaugh this winter? The Wolverines have not won a game in Columbus since 2000.

PAUL SANCYA/Associated Press

Henson quarterbacked that day, completing 14 of 25 passes for 303 yards and three touchdowns (and he rushed for another). Ask him now what the highlight of his Michigan years was, and he doesn't hesitate before answering. Beating the Buckeyes that day.

Problem was, when he was a struggling minor leaguer, impatient to get to the majors, quarterbacking Michigan to that victory in Ohio Stadium didn't exactly play well in Columbus the next few summers. Booooo!

"We're all people," Henson says. "I understand it. In November, we win in Columbus. And in June, I'm playing for their team. The irony was there.

"It was nice to go on the road."

It is enormously difficult to make the majors no matter what the talent level and under the best of circumstances. But Henson during those years became like the umpires: Every game was a road game. Booing Henson became a spectator sport in Columbus. Literally.

Finally, following 332 games and 1,339 plate appearances over nearly three seasons in Triple-A, it probably shouldn't have been a surprise when Henson retired from baseball and decided to concentrate on football after the '03 campaign. He was 23.

"I'm pressing like a mother," he says. "I want to get to New York so bad. And the general situation, when it stops being fun, it stops being fun. It's the nature of your circumstances.

"Being there in Columbus for two-plus years, not having any fun, fighting it every day, getting booed. I lost patience with myself, and there were other opportunities.

"I wish I would have kept plugging. But it just wasn't fun anymore."

As a quarterback, the ball was in his hands. Always, he had the chance to make things happen. So now he did again.


OXNARD, CA - JULY 29:  Quarterback Drew Henson #7 of the Dallas Cowboys walks off the field during practice on the first day of training camp for the Cowboys on July 29, 2006 at the River Ridge Field in Oxnard, California.  (Photo by Stephen Dunn/Getty Im
Stephen Dunn/Getty Images

In Dallas, he met the woman who would become his wife. He got his mojo back. When Vinny Testaverde hurt his Achilles tendon in Baltimore, Henson subbed in and threw a touchdown pass. Click. There went his NFL highlight.

"Yeah, because I never had a chance to play," he says. "Against the Ravens, Ray Lewis across the line staring at you, against a really good defense…"

The next week was the Thanksgiving Day game, and with little recovery time for Testaverde's Achilles, Henson started. He led the Cowboys to a touchdown on their first drive against the Chicago Bears but then threw an interception on an out route. It was 7-7 at the half…and here came Testaverde to start the second half.

Paul Sancya/Associated Press

So it was on to the Lions, his home-state team, which "ironically, wound up being a good experience for me even though we went 0-16 because I wasn't sure if I'd get another chance, I had just gotten married in the summer of '08, and I had spent all of those years in Dallas with my wife's family, and now to be back with high school friends and college friends…"

It takes a village, right? Especially when a dream is dying.

The Lions drafted their quarterback of the future, Matthew Stafford, and let Henson go in the summer of '09. Six years after his baseball career stopped far short of where he had envisioned, now quarterbacking had failed to hold up its end of the bargain.

Free time now on their hands, Drew and Madeleine decided to travel and catch up on things that the athletic seasons had always prevented. Drew dabbled in analyst work on college football broadcasts.

One thing, though, he realized during those broadcasts: He really didn't like talking very much. He wanted to be on the side of doing things, as opposed to talking about things.

So, he reached out to Newman and the Yankees.

And now, on another draft day, Henson is evaluating kids the way the old guys once evaluated him. And yes, he can't help but become nostalgic.

"Yeah, just because that senior season (in high school) was such a whirlwind," he says. "Trying to win a state championship, balancing that with scouts coming in and wanting to see me. Walking three times a game and maybe getting one hit, and the scouts wanting me to take batting practice after the games so they could see me swing.

"I go back to April, May, June of 1998, 17 years ago, and I remember different parts. And it's funny, scouting since March, I come across a lot of veteran scouts who say, 'Hey, I saw you in '97' or 'Hey, you hit for me after a game in '98.'

"It's kind of surreal when they remember you when you were 17 or 18. I try to pick their brains. They have a lot of nuggets."

He is a numbers guy, an information guy. He wants to learn every aspect of this scouting job, maybe pass on some things he's learned to the kids who now are starting down the road he's already run.

CHRIS O'MEARA/Associated Press

Patience, that's his big regret. He wishes he had been more patient in his baseball life. Inevitably, the word "bust" gets tagged with his name but, believe it or not, there is life after 30. And it's a good life.

"Honestly, it was tough for a couple of years, for a few years," he says. "I'm removed from it now. You get a little older, you get a little perspective on things. I've always been so motivated. I've always pushed the envelope, figured I could play college football and minor league baseball.

"Then I got to Triple-A at 21 with barely a year of minor league experience. I was facing experienced pitchers. I didn't have much development. I had no plate discipline to give myself a chance to succeed. Patience was never my biggest strength.

"I would have developed over time. It was coming. I was coming slower than others because I was a part-time player until I was 21. I have no doubts that if I had kept going, whether it would be with the Yankees or anyone else, that I would have gotten to where I wanted to be."

He chuckles. Chick-fil-A nuggets gone, his daughter now is chasing the family poodle around the room with a pirate's hook. It's been said, often, that an athlete dies twice, the first time when his playing career ends. The trick is to realize there's so much more living yet to be done.

Perry Flynn occupies much of Drew Henson's days, on those rare days he finds himself at home before another scouting trip.
Perry Flynn occupies much of Drew Henson's days, on those rare days he finds himself at home before another scouting trip.Drew Henson

So he never made it to Monument Park, but here's the thing: In reinventing himself, Henson still can have a monumental impact on the Yankees.

"Have patience is what I would tell the next guy in my situation," he says. "That's one of the main reasons I wanted to come back and be in player development.

"I had such a unique experience dealing with expectations. Baseball is such an easy game to let get inside your head. Pressing is the worst thing you can do.

"Sharing stories with some of our young guys has been great for me."

And, you can be sure, for them too.

Scott Miller covers Major League Baseball as a national columnist for Bleacher Report.

Follow Scott on Twitter and talk baseball.

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