Here is where I see Alex Rodriguez in 20 years: I see him standing at a lectern in midtown Manhattan — or Fresno, California, or the O’Hare Hilton — and he is smiling. It is a forced smile, an unauthentic smile he wears to all his speaking engagements, but the audience does not care. They see dollar signs, and A-Rod means dollar signs, and that’s why they are here. He warms up the $125-per-ticket crowd with amusing stories about his youth, about his adventures as a precocious, obscenely talented 17-year-old high school baseball player, and they swallow it whole. A fool and his money.

It is at this point that A-Rod begins to lie.

“When I abandoned my agent, Scott Boras, to negotiate my record, 10-year, $275 million contract with the New York Yankees in the fall of 2007, people said I was crazy. They said I left money on the table, or that I could have gotten more money from the Yankees if I had negotiated the contract with the Yankees one month earlier, before I tore up the last three years of my existing contract. What really happened was this: I surveyed the market from all angles and knew that $275 million was the maximum amount I would receive. I proceeded on a course to get that $275 million. I did not care what others said about me, but I did what I knew was right.

“Now, you might not be dealing with contracts that involve that much money — yet,” and here, there will be some chuckles, “but if you stick to your principles, you can succeed in making money beyond your wildest dreams.”

The audience will applaud wildly. A-Rod will smile, activate an overhead projection, and continue his sales pitch. He is the product. He has always been the product. His name is synonymous with wealth. But what is he selling?

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By the time he retires, Alex Rodriguez will have made close to $500 million dollars for hitting, and to a lesser degree fielding, a baseball. The New York Yankees will be complicit in this massive redistribution of wealth, having paid A-Rod around $350 million if he completes the terms of his most recent contract, but by that point, it may seem like a bargain. Forget the actual dollar amounts for a moment, and just realize that far, far worse players than Rodriguez are starting to earn more and more money as baseball’s overall health improves, and the trend points skyward. Rodriguez sought to prematurely capitalize on the expected boom, and publicly lobbied for a 10-year, $350 million contract when he opted out of his contract in October. There were no takers, and he was forced to return to the Yankees, hat in hand and without his agent, and accept their 10-year, $275 million agreement. The contract includes performance incentives that pushes its total value to $300 million if A-Rod breaks the all-time home run record which, barring injury, he should do sometime around 2014. Still, this is a good deal for the Yankees, and a terrible one for entrepreneurial A-Rod. There’s almost no way he could earn any less.

Through his first four seasons on the Yankees, Rodriguez has hit 173 home runs, more than home run kings Babe Ruth, Barry Bonds and Hank Aaron during their age 28-31 seasons. But A-Rod comes with no small amount of baggage. His clunky, obtuse ways made him a poor match for New York, even if, for his attention-starved soul, this is exactly the place he needs to be. Yankees fans, treated to a century of superstars that were either dignified (Lou Gehrig, Joe DiMaggio, Mariano Rivera), too cool to care (Mickey Mantle, Reggie Jackson) or both (Don Mattingly, Derek Jeter) have proven flummoxed by Rodriguez, who has cultivated a public image of an unapologetic masochist.

It seemed like a match made in heaven. A-Rod had come home. Fresh off a World Series loss, their second in four years, the best player since Reggie Jackson would lead the Yankees back to greatness.

Here’s a hit-list of A-Rod’s lowlights from just this year. He was: caught going into a Toronto strip club with a woman who was not his wife; fingered, in the sports quote of the year, as a purveyor of the “she male, muscular” type of stripper by a Hustler club employee; defended, by wife Cynthia, after the strip club debacle when she attended a Yankees game with the words “Fuck You” printed on her shirt, pointed right at the cameras; exposed as a shady landlord at his Florida duplexes by Selena Roberts of The New York Times, who also revealed the piddling donations Rodriguez made to his own charitable foundation; and, finally and most famously, announced he was leaving the Yankees, which he did during the eighth inning of the final game of the World Series. He has since blamed the move on his agent, Scott Boras.

Nearly every time he speaks, he puts his foot in his mouth, and he speaks constantly. He was on 60 Minutes in December, attempting to repair the public relations damage from October, and discuss the Mitchell Commission report on steroids in baseball, in which he was not cited. On television, he tried to sound confident, contrite and thoughtful in an interview with Katie Couric. He said all the right things. He said he never saw players using steroids. He said he understood why the media was so hard on him. He said that he wasn’t speaking to Boras, the agent who ostensibly put him in this mess without his knowledge. He called the situation “unacceptable” and “inappropriate.” And then he said he would keep him. Couric did not ask why.

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Alex Rodriguez was born in New York City’s Washington Heights neighborhood, but moved to the Dominican Republic with his family at the age of 4. The family eventually moved to Miami, and his father left the family permanently when Alex was 9. A-Rod was the first overall draft choice by the Seattle Mariners in 1993, and signed with the Texas Rangers in the boom market of 2000 for 10-years, $252 million. Three years later, fed up with three last-place finishes, Rangers owner Tom Hicks would trade Rodriguez to the Yankees just to be rid of him.

It seemed like a match made in heaven. A-Rod had come home. Fresh off a World Series loss, their second in four years, the best player since Reggie Jackson would lead the Yankees back to greatness. Here’s what happened instead: with A-Rod, the Yankees lost more often, watched Joe Torre leave and saw the Boston Red Sox, their historical punching bag, win two World Series titles in four seasons.

And here’s the moment where A-Rod had the chance to be a hero, despite all that. It is October 5, 2007, and we’re in Cleveland, home of game two of a playoff series between the Indians and Yankees. The score is 1-1 in the ninth inning, as the Indians recently tied the game after a swarm of flying insects attacked Yankees pitcher Joba Chamberlain, forcing him to throw two wild pitches. A-Rod is up. He has made an out in his last 18 playoff at-bats; a single here will erase not only these bad memories but those of the 2006 playoffs as well, where he was practically invisible as the Yankees fell from the sky. There have been eight pitches in the at-bat, and the ninth is on its way. The count is full.

The pitcher is Fausto Carmona, 23. In 2006, Carmona was a relief pitcher for the Indians with several high-profile blown saves to his name; all he did was enter the starting rotation in 2007 and reel off 19 wins, second-most in the league. Now here he was, 26 outs into a game where the best starting pitchers usually last no more than 21, and he’s facing the best player in baseball, a living great, with Chironomus plumosus in his face (common name: “midges”) and the game on the line.

Something has to give. Though Rodriguez has struck out twice earlier in the game, he’s obviously seeing the ball much better now; a lesser batter would be long gone, as Rodriguez has fouled off each successively awesome pitch. Carmona’s final pitch is 95 miles per hour, just below Rodriguez’ hands, in a spot where it is virtually impossible to hit and equally foolhardy not to try. Seeing this, A-Rod swings, and misses. The inning is over. The game continues. The Yankees will lose, and be eliminated from the playoffs three days later.

These are the dynamics of baseball: A-Rod can’t do it alone, and even if he could, sometimes there’s a Carmona to stop him. He’s not the first to carry the burden of “best player in the league who can’t win a title.” Neither Ted Williams nor Barry Bonds — commonly considered as two of the best five all-around batters of all time, if not the two best — won a World Series title. Each new generation of baseball fans yearns to see the emperor without clothes. Williams hated the media for it, and Bonds is more or less a misanthrope. A-Rod has carved out a third way — he plays to the media even as they tear him apart, and uses the slights as fuel for his ego and his constant, self-defeating drive for attention. “When people write [bad things] about me,” he told Sports Illustrated, “I don’t know if it’s [because] I’m good-looking, I’m biracial, I make the most money, I play on the most popular team.” On 60 Minutes, he boasted about his “strong, dominant position” in baseball. You don’t hear Derek Jeter, A-Rod’s teammate late of four World Series-winning teams, crowing about his own looks or his salary, because it doesn’t take a high school degree to know that it’s unbecoming to talk about yourself so flatteringly, and that if you do, the only thing you invite is more criticism.

If there is an athlete whose cachet A-Rod aspires to, though, it is not Jeter’s. It is that of Tiger Woods. A-Rod and Woods are both prodigiously talented and maniacally hard workers, but whereas life is a chore for A-Rod, Woods makes everything look easy. Woods smiles, and plays with the media; A-Rod scowls, and parries with reporters. Woods designs golf courses and donates heftily and visibly to his charities of his own making; A-Rod barely gives to the A-Rod Family Foundation, according to the Times’ Roberts. Woods accepts the attention that comes along with his status as golf’s greatest winner, but told ESPN.com that he’d “much rather have anonymity but still go out and kick everybody’s butt… As long as everyone I competed against knew I beat them, and for me to know as well — that would be enough.”; A-Rod confuses the attention over his clunky, failure-prone personality with status as the game’s most popular player.

And then there’s dad. Woods’ father, who passed away in 2006, was his mentor, sidekick and hero. You can probably draw a straight line from their relationship to Woods’ singular mental toughness. The opposite could probably be said for Rodriguez, but only he knows for sure. If A-Rod is the model athlete in any way, it is through his public embrace of therapy, which he says has helped him tremendously (And his wife, Cynthia, is a psychologist). But that room is closed.

Add all this up, and that’s why I can see him on that lectern. The product A-Rod’s currently selling — himself — is the “powerful, dominant” figure who can impress people with numbers, money and looks. Woods’ strength comes from the core, and emanates outward. The attention bores straight into A-Rod, and that’s why that smile at the lectern won’t be authentic. He’s not selling a way to be happy, or even a way to be rich. He’s not selling a solution. Hucksters don’t sell solutions. He’s selling an escape.

In a way, A-Rod has more in common with Rudy Giuliani, the world’s most famous New Yorker and to whose presidential campaign A-Rod donated money in 2007, than he does with Woods, Jeter or any other athlete. Giuliani would almost certainly have been relegated to low-level political huckster status after his up-and-down mayorship, except for 9/11; if Rodriguez can pull off a miraculous late career championship, his past will similarly be forgotten. He has the chance to make his own escape.

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Back to 60 Minutes. A-Rod’s apologies for October are letter-perfect (“If I was a fan, I would have been very, very upset”), but they still seem phony and rehearsed. He comes off like a politician and speaks in a slightly accented monotone. His hair is perfect.

But later on, there’s a rare window into the real A-Rod, when he led the baseball knowledge-starved Couric on a tour of his training facility. He hit baseballs for her, explaining with the editorial ‘we,’ how he has learned to keep his arms close to his body to swing with maximum efficiency. Couric cooed as A-Rod dialed the pitching machine up to 90 miles per hour and rhythmically raked pitch after pitch back into the wall. She asked him about his thought process, and he said he often visualized being in Yankee Stadium, with two outs in the ninth inning. The next pitch came, and he cracked it harder than all the others. He stopped. That was it. That was the moment. The one people have been waiting for. He turned to Couric and positively beamed. “Home run,” he said.

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