Drew Henson

He was a two-sport phenom who never made his mark in either one as a pro (though he did make millions). Now he's back in the game, bird-dogging for his old baseball team, trying to find future studs and sweating the details

IT'S THIRSTY THURSDAY at Bright House Field in Clearwater, Fla. Women with sunburned shoulders and wedge heels clomp around the ballpark with a drink in each hand. Hooters waitresses serve a corporate party in a section near the third base dugout. Silver-haired dudes in Tommy Bahama shirts gravitate toward the two-for-one specials at the straw-roofed bar looming over the leftfield stands. It feels as if happy hour is masquerading as a baseball game.

Seven rows behind home plate Drew Henson—the former Yankees third baseman and Cowboys quarterback—is as oblivious to the revelry as the fans are to him. A white towel over his shoulder, he cracks a lemon-lime Monster energy drink to stave off the heat of a soupy May evening while he evaluates the Clearwater Threshers (a Phillies affiliate) and Charlotte Stone Crabs (Rays) of the Class A Florida State League. Henson, 35, once drew comparisons with the Broncos' John Elway and the Phillies' Mike Schmidt. Now he's working for the Yankees as a scout—one of the defining prospects of the past generation trying to identify the stars of the next one.

Minutes before the first pitch a thunderstorm chases Henson under cover, where he pulls up one of his four iPhone weather apps and laughs about how his new job requires him to forecast more than playing potential. "Hurry up and wait," he says.

Henson knows the feeling. In the rush to fill the impossible expectations that came with his astonishing career statistics at Brighton (Mich.) High—52 touchdown passes and 5,662 yards and a then national record 70 home runs—Henson didn't stick to a single sport long enough to allow him to thrive as a pro. He'll never know the answer to the million-dollar question, as he calls it: What if he'd dedicated the raw talent in his 6'5", 220-pound body to just one game? Instead, his final MLB and NFL statistics serve as a cruel tease: one major league hit (a single off Orioles lefty Eric DuBose in 2003) and one NFL touchdown pass (to wide receiver Jeff Robinson against the Ravens in '04). Each ball sits in his home office.

He wound up less of a star and more of a stargazer. He split snaps with Tom Brady (Michigan), fielded alongside Derek Jeter (New York) and passed to Keyshawn Johnson (Dallas). He played for three Hall of Fame coaches—Lloyd Carr, Joe Torre and Bill Parcells—and signed with two of the most driven owners in sports, George Steinbrenner and Jerry Jones. (Henson's mother, Carol, once asked of the man everyone called Mr. Steinbrenner, "George, what do you think of your character on Seinfeld?" Drew and multiple Yankees officials nearly choked on their steaks.)

"I've had so many different experiences and played for different coaches and franchises," Henson says over tacos one night. "I've seen what's worked and what hasn't worked." Then he adds with a wry smile, "And I've been on the 0--16 Lions."

That woeful 2008 team in Detroit was Henson's last gasp. In the spring of '01 he left Michigan football after three seasons to pursue baseball full-time. A righthanded hitter, he played 501 games in the minors but only eight in the big leagues. Then, as he was showing signs of breaking through in baseball—Henson hit 40 doubles and 14 home runs in Triple A in '03—he walked away from the remaining $12 million of a six-year, $17 million contract to try the NFL because he missed having a ball in his hand. He signed with the Cowboys for $3.5 million. But a lack of reps and three years away from the gridiron limited his chance for success. He played for the Cowboys, Vikings and Lions, starting just once. "There's no doubt in my mind that if he had even played one more year [in Ann Arbor]," says Carr, "he would have been very successful in football."

The Lions cut Henson days after picking Matthew Stafford No. 1 in the 2009 draft, prompting an interval of travel and self-discovery. With his wife, Madeleine, he hopscotched the globe with a spontaneity that a regimented sports life had never allowed. They blew off a flight because they were on a hot streak at the blackjack tables in Macau, watched Muay Thai fighting in Bangkok and saw Drew's favorite soccer team, Barcelona, eliminate Real Madrid in the 2011 Champions League semifinals. "It was almost like doing retirement in reverse," Madeleine says.

AT HOME in Dallas, Henson dabbled in finance and broadcasting, but he missed the camaraderie and competition of sports. He called the Yankees in the late spring of 2012, and they hired him to help coach during the Instructional League that fall—meaning the day after he and Madeleine told friends and family they were pregnant, they announced they were moving to Tampa, where they now live with two-year-old daughter Perry. Henson worked as a hitting coach in the Gulf Coast League in 2013 and '14, then transitioned to scouting this season. "You don't know where it's going to lead," Henson says. "But I like the thought of putting teams together and profiling the right types of guys. I find it fascinating."

Henson doesn't enjoy delving into the psychology of his career—"That's been done," he says—but Madeleine saw a change once he started going to the park again every day. "When he was done playing, it kind of felt like, Why was I given all this talent, and it didn't turn out the way I thought?" she says. "I felt like there was a period of searching. Going back with the Yankees was kind of like that aha moment."

Earlier this year New York paired Henson with veteran scout Joe Caro, and the duo met for two to three hours a couple of times a week. Caro's advice ranged from prudent—sign up for Marriott and Hilton rewards programs—to practical. "That dude can sweat with anyone," says Caro, 56, who has been with the Yankees for 22 years. "I told him, 'You're going to need more than a handkerchief. Don't be afraid to take a towel from the hotel room.'" Henson, an eager student, arrives at the stadium with a white towel draped on his shoulder à la John Thompson Jr.

SCOUTING A baseball game is an intricate operation, which Henson is still learning. Splayed in front of him in Clearwater are three charts, each a different color, that he fills out during the game. There's one for each pitcher and the last is to evaluate the Charlotte hitters. (Henson says experienced scouts can do both teams' hitters at once.) He tracks every pitch by type and notes the arm action, arm angle, location, delivery and velocity. He uses a stopwatch to time batters running to first, catchers throwing to second and the pitchers' release to the plate. "It's slowing down for me," he says. "It was going real fast the first few months and still is at some points."

Caro thinks his student is progressing just fine. "He struck me as a humble guy who wants to do well at his craft," he says. "Lots of times very good players do not become very good coaches or scouts. They never had to work at it."

Henson has embraced the scout's life and the challenge of projecting what a 17-year-old prospect might develop into at 25. He covers about 15 minor and major league teams and will cover them for five games—to see each starter—and then files a report on all 25 players that takes 30 to 40 minutes per man. Henson, like many former pros, had no idea how detailed a scout's work was. "I'd like to go back and see some of my grades at different ages," he says. "It may have helped."

Any objective input would have been useful to cut through the attention, expectations and notoriety Henson began to attract in high school. SI profiled Henson in 1998, when he was 18, citing the number of Yahoo! search results his name generated to quantify him as the first über-recruit of the Internet age. Even at the Yankees' Triple A affiliate in Columbus, Ohio, the former Wolverine heard boos from Buckeyes fans during every at bat. These days he's only recognized by the occasional octogenarian memorabilia junkie who'll ask him to sign cards. Taking two-week trips to Jacksonville; Charleston, S.C.; Myrtle Beach, S.C.; Hickory, N.C.; and Raleigh can mean that some days his only in-person conversation is scout talk between innings. ("Was that a slider or a slurve?") He has seen the endless promotions to enliven parks, from Game of Thrones night in Durham, N.C., to Frozen night in Bowling Green, Ky. Instead of monotony or loneliness, Henson has found fulfillment. "It's fun," he says. "I'm getting to do something I love, in an organization I grew up rooting for and playing for."

The feeling is reciprocated by the Yankees, who value Henson's work ethic and perspective. Henson made more than $10 million in his playing days and invested well, which may make his willingness to traipse to small-town ballparks night after night seem strange. But Henson grew up in sports. His father, Dan, was a college football assistant, and his mother worked as a high school phys-ed teacher. "Drew doing this isn't a head-scratcher if you know him," says Billy Eppler, the Yankees' assistant general manager.

Henson is new to his job, but he has hopes of advancing. "I'd like to be in the room sharing an opinion with people who work for a major league club," he says. For now, he sweats through Thirsty Thursday—another night in another park—and relishes the grunt work. It feels good to be back in the game.

He'll never know the answer to the million-dollar question: What if he'd dedicated the raw talent in his 6'5", 220-pound body to just one game?

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Photograph by Chip Litherland For Sports Illustrated

SCOUT'S TAKE The son of a football coach and a gym teacher, Henson follows about 15 teams for the Yankees from his base in Tampa.

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DUANE BURLESON/AP (MICHIGAN)

TAKING THE LONG VIEW He was the starting QB at Michigan but left to play for the Yanks, who called him up from the minors for just eight games.

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CHRIS O'MEARA/AP (YANKEES)

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CHIP LITHERLAND FOR SPORTS ILLUSTRATED

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