This post is part of our feature on Money Losers of 2008. See all 20.

Some claim that Madonna has brainwashed Yankee's third baseman Alex Rodriguez, which I find hard to believe; from what I've seen of her in interviews, she barely has adequate brain matter for herself, much less extra to share. And A-Rod; you make a bazillion dollars a year, dude. If you're going to cheat on your wife and 10- week-old daughter (you dog), this is the best you can do? A woman 16 years your senior with some serious mileage on her, um, moneymaker?

The reported affair cost them each a fortune. A few years ago, Rodriguez received a $275 million contract with the Bronx Bombers, which has come out to around $6.7 million per each postseason hit so far. (Choke much?) A-Rod's jilted wife, Cynthia, sued for divorce, and the couple was officially kaput by September. Settlement terms were not disclosed. Meanwhile, the Yankees, still in need of a clutch hitter, are shopping for Manny Ramirez, who could eclipse A-Rod's baseball star (and his star endorsement value, already damaged by the bad press surrounding his divorce).

At the same time, Madonna was buying her way out of marriage to Guy Ritchie for an estimated $76-92 million. That's a lot of material, even for her.

A-Rod was rumored to share Madonna's interest in Kabbalah, rooted in Jewish mysticism. When it comes to mystery, though, not many are as perplexing as the pairing of these two. What do they share, except funny work uniforms and too much dough? Well, not so much dough, now.

Be sure to check out more Money Losers of 2008.

In 2001, Alex Rodriguez, perhaps the finest slugger to ever play the game, inked an unprecendented 10-year, $252 million contract to jump from the Seattle Mariners to the Texas Rangers. Three years later, when the Texas management regained its sanity and realized the ruinous terms of the deal, they dealt A-Rod to the only team with the money to support such a contract, the New York Yankees.

With A-Rod and another future Hall-of-Famer at shortstop, Derek Jeter, the Yankees had the foundation to return to its status as perennial World Series champion. Unfortunately for the club, it hasn't turned out that way. For A-Rod, however, things continue to improve.

His 2007 season was a monster; 54 home runs, 156 RBIs, slugging percentage of .645, American League MVP. Unfortunately, he continued what has become a maddening tendency to disappear in the playoffs, hitting like a bantamweight in the team's loss to the Cleveland Indians.

Such a wipeout might diminish most people's bargaining value, but A-Rod took an early-out option in his contract and went back out on the free agent market. After much bluster and posturing, the Yankees awarded him a new 10-year, $275 million contract. At 32, he should be set for the rest of his career, one in which he will almost certainly eclipse the home run record of Barry "better hitting through chemistry" Bonds.

When it comes to baseball contracts, in 2007 A-Rod hit one out of the park.

Be sure to check out more Money Winners of 2007.

It was less than 3 weeks ago when Alex Rodriguez decided that the middle of World Series Game 4 was the opportune time to announce he was ditching the Yankees through a clause in his contract. At the time, Howard Stern sidekick (and lifelong Yankees fanatic) Artie Lange quipped: "Don't let the free-agency door hit you on the way out" (I'm paraphrasing to keep it clean, folks).

In the wake of this stunt, our own Georges Yared referred to A-Rod as a "crybaby extraordinaire" and a "selfish, self-centered you-know-what." Georges also noted that, "The attempt to upstage the Red Sox and Rockies should not be forgiven nor forgotten by the baseball brethren." Indeed, it was a classless move, one likely perpetrated by A-Rod's agent, but certainly given the green light by the third baseman himself.

And yet, here it is mid-November, and hijo pródigo A-Rod and the Yanks are back at the table. It's all sorts of amusing, really. This morning, it hit newswires that negotiations mediated by Goldman Sachs (NYSE: GS) officials have resulted in a new contract for the clutch player who isn't. Reportedly, A-Rod wanted to restart negotiations with the team, but chose to use a third party (Goldman representatives) instead of his agent, Scott Boras.

Yesterday, during the Boston Red Sox' sweep of the upstart and exciting Colorado Rockies, crybaby extraordinaire Alex Rodriguez decided it was "the time" to announce he was opting out of his contract with the New York Yankees and filing for free agency. He had to make a decision within 10 days after the World Series ended, not within 10 minutes of the start of Game 4.

What a selfish, self-centered you-know-what. This guy is a total and complete goofball. Sure his stats are fearsome, but he has never won at any level a championship. He had great numbers on flailing Seattle Mariner and Texas Ranger teams, but both rarely played .500 ball. After four seasons with the Yankees, Mr. No-October has taken the chicken's way out. The attempt to upstage the Red Sox and Rockies should not be forgiven nor forgotten by the baseball brethren.

This guy comes to New York and played next to Derek Jeter -- a real ball player. Jeter will never hit the home runs that A-Rod does -- Jeter has 195 career home runs in 12 seasons, compared to Rodriguez's 500 and some. But Jeter has won more games than A-Rod ever will. Derek Jeter may be one of the most clutch players and hitters to ever play the game. Jeter may go 0-4 in a game but make a diving stop at shortstop to kill an opponent's rally. Jeter may get the stolen base at the right time to start a rally: Jeter will sacrifice himself and hit the ball to the right side to move a teammate. Bottom line, Jeter is the complete player. With him, it's all about team.

With A-Rod -- it's all about him. In the playoffs, Rodriguez has been a total and miserable failure. Jeter is clutch. In the playoffs, year-in and year-out, Derek Jeter is the toughest out. Rodriguez is 0-18 in the playoffs with runners in scoring position: the ultimate barometer.

The Boston Red Sox won the World Series last night, so what is the baseball world buzzing about today? In the same way that the antics of train wrecks like Britney Spears steal headlines away from others with worthy accomplishments, we are writing about the Yankees and their messy divorce from future Hall-of-Famer Alex Rodriguez. Yesterday, A-Rod's agent, Scott Boras, announced that the third-sacker would take his option to terminate his 10-year, $252 million contract early and put himself up for auction.

In the typical classy Yankee way, Steinbrenner the Lesser, Hank, took the opportunity to blast the player, telling the New York Daily News, "He doesn't understand the privilege of being a Yankee on a team where the owners are willing to pay $200 million to put a winning product on the field."

After years of being crucified by the New York press, fans and front office for failing to hit enough to overcome a minor-league starting rotation and a gaggle of overpaid, over-aged teammates, who wouldn't want out?

The question now is who will step forward to pay A-Rod more than his previous contract? No other team enjoys the Yankees' attendance or media income. Fortunately, we're not talking Wall Street, but baseball, and business economics are not its forte. Remember that A-Rod signed his huge contract with Texas, who, when they came back to their senses and realized they couldn't cover that salary, were forced to deal him to New York while agreeing still to cover part of his salary.

Boras, known as the superagent, is too shrewd to make such a move without confidence that a least a couple of teams will contend to sign the best player in baseball. The Chicago Cubs could use his talents, although last year's signing of Alfonso Soriano tied up a lot of Chicago's cash. The Cubs could also go on the block soon, as well, and a lot of debt might not help that.

Is the most-storied franchise in baseball history for sale? The New York Times Dealbook speculates that with YES, the Yankee's television network currently up for sale, that the team itself might not be too far behind. Much of the speculation is based on a recent article in Fortune magazine. There are rumors that owner/lunatic George Steinbrenner's health is deteriorating, and he has been less openly crazy than in the past. (Full disclosure: I am a die-hard Red Sox fan, and one of the highlights of my life was watching Jason Varitek stuff his mitt in A-Rod's face.)

According to Fortune:

The topic of a sale "comes up all the time" in conversations with the other partners, says Yanks minority owner Edward Rosenthal, a retired steel executive. Adds another Yankees limited partner: "If I were handicapping it, I think we're looking at a sale of the team within three or four years."

The Yankees are estimated to be worth around $1.5 billion, but with hedge fund/private equity managers lining up to cash out their stakes with IPOs, it seems like it could go for even more -- perhaps a lot more.

Assuming The Boss's health is OK, that still raises the question: How much longer before he gets sick of losing?