For Joe Maddon, the answer is easy: He'd be Jack Kerouac, beating the road for an alternative baseball generation, or the Dennis Hopper character in "Easy Rider."
Maddon, the 54-year-old grandfather who grooves to the Stones' "Start Me Up" while making out his starting lineups, is the freshest thing to hit the World Series since ... well, since the Tampa Bay Rays.
He is No. 70 in your scorebook -- the highest ever for a Major League manager. His black-rimmed glasses are already baseball's most recognizable specs since those coasters Harry Caray wore. When the Rays needed one more push over the American League East top in mid-September, he showed up with a Mohawk.
And don't ever ask him what's on his iPod -- unless you've got a lot of time to kill.
He speaks from the heart and speaks to the truth. In a pre-fab baseball world, where the conventions and strategies never change, only the people acting them out do, he builds castles in the sky out of hunches.
But while Maddon's head is in the clouds, his feet are firmly on the ground. He has traveled far, without forgetting where he came from, the close-knit Pennsylvania community of Hazleton -- 81 miles west of Philadelphia, where the 2008 World Series will resume with Game 3 on Saturday, and 380 miles from Northfork, W. Va., Phillies manager Charlie Manuel's hometown.
Two men, straight out of Norman Rockwell's America. Alike, yet different, a contrast best illuminated by this:
The night his mother passed away, Manuel managed Game 2 of the NLCS, and he stayed in the dugout through three more games before the funeral. Maddon interrupted his first season as manager to attend the law school graduation of his girlfriend on the other side of the continent.
But while Maddon is the one who somewhere along the way veered a little closer to Andy Warhol, and he now prefers a drink that comes with a cork instead of a pull-tab, Hazleton remains his anchor.
His page at a baseball Web site which offers such opportunities is sponsored by "the gang from Casamato's," a Hazleton restaurant owned by Maddon's childhood bud, Dave Cassarella and his wife, Terri D'Amato, who in their accompanying message urge, "Go Joe, shock the world!!!!"
In that world of people who spend a lifetime chasing acceptance by others, Joe needs to answer only to the person who stares back at him from the mirror every morning.
Of course, in early February, even that reflection had to be telling him, "You're nuts."
Maddon had checked in for his third Spring Training with the bottom-feeding Rays with his head keeping those castles company in the sky.
"I was worried about him," one of his pitchers, Andy Sonnanstine, would admit later.
Worried, as in, "Let's get the white coats on speed dial."
Which just raises this issue: Were someone to channel Norman Vincent Peale and ask him, "If you weren't a philosopher, who would you be?" he would answer, "Joe Maddon."
Maddon's chronic positive thinking never had a chance to blow up in his face because the young Rays, a franchise that had spent its entire 10-year existence in the loss column, broke through .500 on April 25 and just kept rising.
And if they weren't young, they couldn't have done it. A team of crusty veterans would have laughed off, rejected Maddon -- as other veteran teams have resentfully undermined managers who never played the game professionally.
As the greenest of the Rays, one-month Major League veteran David Price, said in the aftermath of their biggest triumph, Sunday night's pennant clincher over the Red Sox, "There's probably one person in this locker room that really thought we could do it, and that's Joe Maddon."
And if he was going to do it, there is no question Maddon only wanted to do it on his own terms. He hadn't devoted a lifetime to developing his own theories and ideas only to conform when finally given a chance to test them in practice.
It had been a long wait. He spent more than two decades in the Angels organization -- Minor League instructor and manager, Major League coach -- and in the shadows.
Maddon had been a finalist for the Red Sox managing job five years ago, but Boston opted for Terry Francona. But then the Rays were looking for someone to replace Lou Piniella, the Tampa native who threw up his arms in resignation and walked out on his dream job in 2005.
After listening for three years to Piniella's cynicism, GM Andrew Friedman and club president Matt Silverman and owner Stuart Sternberg found themselves listening to Norman Vincent Peale.
They liked him, and his message, which soon enough would manifest itself in all those slogans that form framed galleries inside the Rays' locker room. The fancy, lyrical words boil down to a couple of simple themes: Accountability, and faith.
"Yeah, that's kind of what the point is of all his slogans," pitcher James Shields said. "You've got to believe in yourselves before anybody else does."
You also have to be comfortable in your own skin. Maddon luxuriates in it. No one in baseball thinks so far outside of the box, whether the topic is the daily commute or late-game pitching moves.
Maddon has logged more miles on his bicycle than has Lance Armstrong. Watching some of his strategic decisions, some people think he must've suffered some spills before helmet laws: Trusting Price to close out Game 7, in what was the eighth appearance of the left-hander's entire big league career, was a classic example.
Maddon has as much confidence in himself as he wants his players to have in themselves.
Even before being offered the job of managing the Rays, he told his potential bosses that he would need a few days off in the coming season: His girlfriend would be graduating from law school in California, and he couldn't miss the ceremony.
Jaye Sousoures is his fiancee. Marriage is just around the postseason corner, and Maddon anticipates the event with continental zeal.
"I'm looking forward to hopefully successfully concluding this whole thing," he said, meaning the World Series, "and getting on a plane and getting over to Rome, getting off there and just putting a backpack on and hitting the trains and just having a good time."
That honeymoon awaits. This one is still in full bloom.