When first baseman Steve Pearce lofted Baltimore’s second home run of the ninth inning over the left field fence at Yankee Stadium last Thursday night, Derek Jeter remained in his crouch at shortstop. He didn’t even turn around. The Orioles had tied the game at five with three runs off dependable closer Dave Robertson and suddenly a collective hush fell over the 48,600 faithful assembled to give the Captain his send-off. This wasn’t supposed to be happening. Could Derek Jeter possibly lose his last game in pinstripes? Then, like seemingly every clutch moment he had on a baseball field, the stars aligned for Derek Jeter one final time.

“It was above and beyond anything I’ve ever dreamt of,” Jeter told the press minutes after winning the game on an opposite field (of course) single in the bottom of the ninth.

What’s next for a man who has spent nearly every day of his adult life adhering to a strict routine? Who, by his own admission, has never gone to a summer bar-b-que because he’s been at the ballpark almost every weekend from March through September (and well into October) for 20 years? What does the future hold for a one-man sports marketing brand whose mere appearance among the great unwashed masses sparks hero worship on a Michael Jordan-esque brand?

For a man facing such unique uncertainty, one thing seems assured: as his life moves into its next phase, Derek Jeter will do whatever he wants.

“It’s hard to imagine anyone having a greater reputation than Derek Jeter does right now,” says longtime sports agent Jerrold Colton, who has represented the likes of NFL stars Boomer Esiason, David Akers and Leigh Bodden. “I don’t think you could have a better public figure athlete to identify [your business] with than Derek Jeter. He embodies everything you could possibly want to convey about your company, whether it be character, loyalty, longevity, high morals or success.”

It’s hard to know exactly where Jeter’s business deals will take him. It seems assured he will continue his work with his Turn 2 Foundation, which has put $19 million in grants into programs promoting healthy lifestyles for kids. Big-name endorsements with Gatorade, Nike and Movado, estimated to net him $9-$10 million a year , are expected to follow him into retirement. Yet one could imagine the Captain’s post-playing career reaching well beyond the realm of foundation caretaker, company pitchman or motivational speaker.

Last year, Jeter announced a partnership with Simon & Schuster publishing to start his own imprint. In January, he became a partner and brand development officer of health food marketer Luvo. In terms of the breath and reach of those companies, one could envision Jeter becoming a sports entertainment mogul on par with other successful athletes-turned-businessmen like Jordan and Magic Johnson.

“It all depends on how he wants to chart his course,” says Rob Roche of RSR Sports Management. “I could see him in broadcasting and possibly ownership or front office of a team.”

Jeter has expressed an interest in ownership. His name recognition and vast reserves of good will built up over 20 blemish-free years in New York could make him a popular candidate to front an ownership group. It seems unlikely that Jeter would have enough on his own to purchase a marquee franchise, though his holdings are vast. Jeter made north of $265 million as a member of the Yankees. That, coupled with his earnings from endorsement partners, puts his total career earnings around $400 million, according to Forbes.

One thing that seems highly unlikely is politics, though given Jeter’s outsize popularity, it doesn’t seem utterly ridiculous. A New York Magazine reporter got Jeter to admit he voted for Barack Obama in 2008, but it was a bit like pulling teeth.

“I don’t have to get into politics,” Jeter says. “My job is a baseball player, so I stick to what I know best.”

As Jeter celebrated his final walk-off moment at Yankee Stadium Thursday night, awash in the cheers and swamped by teammates, questions of the future could certainly wait. Fans may not know where his post-playing days will take him, but a jersey retirement ceremony and a day in Cooperstown are among the few events that are assured.

“The good part,” Colton says, “is I don’t think Derek Jeter is going to disappear.”

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