In This Corner: Battle of Her Madgesty's Boy Toys

Back in the day, when Madonna sang about La Isla Bonita, we figured it to be Cuba. But could Alex Rodriguez's native Dominican Republic be where her Madgesty longs to be? Either way, one thing we know for sure, Madonna's true love is not just for the island breeze, but for the men it breeds.

Enter the ring, Carlos Leon, a Cuban American personal trainer and father to Madge's first born child, Lourdes Leon, and Alex Rodriguez, the Dominican by-way-of Washington Heights baseball player who's jockeying to become father to her next one.

A-Rod may be the pop icon's flavor of the moment, but Carlos has proven he has staying power. Which one has what it takes to become the next Mr. Madonna? We'll let them settle it in the ring...

Round One: Daddy Dearest

We know Madonna's children are at the top of her list of valued possessions. She carefully hand-picks each one, whether from a remote orphanage in a developing country, or the "specimens" from which she breeds her own. Needless to say, fatherhood abilities will be a big deciding factor in the fight for her heart (and bank account).

A-Rod isn't winning any MVPs in the parenthood category. He reportedly bolted from wife Cynthia Rodiguez minutes after she gave birth to their daughter Ella to be with his "f*cking soul mate" Madonna, and has reportedly been spending more time with the Material Girls kids than his own since his divorce.

Carlos, on the other hand, has turned it around like Kevin Federline this year. He was snapped several times holding hands with his daughter Lourdes, saying that the two "talk everyday." He also credits himself with balancing out the jet-setting lifestyle Lourdes has with her mother by keeping his little princess down-to-earth when she's in his custody.

Winner: Carlos Leon, because we wouldn't even trust A-Rod to look after our pet rocks.

Round Two: Dolla Dolla Bill, Y'All

She's living in a material world, and Lord knows she's a Material Girl. Yet somehow, Madge has always picked the ones who have been light in the pocketbook, relatively speaking. We all know Carlos Leon makes less per year than Madge spends on flying in a special breed of blueberry from Canada to her London estate (true story), and Guy Ritchie, though he isn't exactly standing in line for a welfare check, has allegedly always preferred to live—extravagantly—off Madge's riches.

Alex Rodriguez, by all accounts, is a break from Madonna's tradition of dating moochers. He has his own half-billion dollar fortune from his baseball contracts and endorsement deals. Even in our gutter-level economy, Alex is reportedly throwing down a whopping $80 million for a penthouse apartment two blocks from Madge's Central Park West triplex, just so he can be close to her without getting too much in her way. What's more, rumor has it Alex has committed to building a his-and-hers gym complex for the two of them near their respective abodes. In their workout-obsessed world, that's practically an engagement ring.

Winner: Alex Rodriguez, because it must be nice to date a man who can not only pay for dinner, but offer up hundred dollar bills for you to wipe your mouth with.

Round Three: Spiritualized

Third in priority only to her children and fanatic workout regime is Madonna's dedication to Kabbalah, the mystical offset of Judaism. Kabbalah has outlasted any of the other trends in Madge's life—men, personas, hair colors—and any beau of hers had better look good in a yarmukle, or go by way of Guy Ritchie.

Both Carlos and Alex have shown considerable tolerance for the controversial religion by attending Kabbalah classes and services with her Madgesty, but only Alex has taken the extra steps towards conversion. He donated a half-million dollars to Kabbalah earlier this year and supposedly even has his own spiritual counselors.

Winner: Alex Rodriguez, because mere tolerance may keep Madonna cutting those alimony checks, but only total devotion will win her heart.

OVERALL WINNER: Carlos Leon. We know A-Rod took two of the three rounds, but does anyone seriously think he's more than a passing fad? We have a feeling once Madge has had her fill of whipped boy toys, she'll come back to the only one that's stood the test of time as a good father, and an even better friend.