Master Debating Myself

Leo vs Jeter

Series Record: MASK 3 Gus 1

After a surprising win in the Olympics debate, Marcus Antonio San Keota finds himself with a two debate lead. This week we look at two top bachelors of the past 20 years, Derek Jeter and Leonardo Dicaprio, and debate which life would be better to have. We take into consideration, career, lifestyle, and most importantly the women, oh the women.

This picture says 10,000 words.

This picture says 10,000 words.

MASK: Considering my superior debating skills, I shall go first. And for me, the choice is easy. Give me the life of premiere thespian Leonardo Dicaprio.

Gus: Nerd alert! You would choose an actor over a premiere sports star.

Stud has been replaced by the word Jeter

Stud has been replaced by the word Jeter

MASK: Is baseball still a sport? I hadn’t noticed.

Gus: You know who has noticed? The over 2 million followers on his Facebook page. How many do you have?

MASK: Same as you, dummy. Want to talk Facebook page Leo has…

Gus: No! I don’t want to talk Facebook page. Let’s talk championships, as in five World Series championships. How many Academy awards does Leo have again?

MASK: Acting is not about winning trophies. The goal is to win over the American public by either pandering, ala Tyler Perry, or earning its respect ala Leo. Pandering may lead to lots of money, but the respect earns you a better place in the history books.

Gus: It’s your fault for wanting a career with no clear standard of judging success. Jeter plays for the richest franchise in American sports and has delivered five championships as the face of said franchise. Personally, I hate the Yankees, but my hatred does not blind me to the fact that if you deliver for them and the city of New York, you’re set for life. Like Sinatra said, “if I can make it there, I can make it anywhere.”

MASK: Want to talk New York? Leo has made it with Mr. New York, Martin Scorsese. He has starred in five Scorsese films, only Deniro has been in more. Plus he helped him finally break through and win his first Academy Award for best director.

Gus: The New York Yankees are better known around the world than Scorsese. Jeter can go to any country and instantly get a celebrity bump.

He was set for life after this.

He was set for life after this.

MASK: Yeah, you’re right. Cause people around the world wouldn’t recognize the star of that little movie about a boat crashing. What was that called again? Oh yeah, mother fucking Titanic. The mother fucking is now trademarked. It was only the highest grossing movie ever, till that stupid Avatar movie bumped it off. The first movie to break the billion dollar mark. I think Leo gets plenty of celebrity bump.

Gus: Whatever, he still had to spend a significant time with Billy Zane to earn that big bump.

MASK: And Jeter had to do the same with A-Roid.

Gus: Touche. Alright, enough of this bullshit. Let’s get to the meat of the argument. Women. No one has a more impressive roster of conquests than Jeter. He’s dated both a former Miss USA winner, Vanessa Minnillo, and a Miss Universe, Laura Dutta. No other man can claim he has pulled off the Miss USA/Universe double play. Pun intended.

MASK: Please, Leo has been inside more  supermodels than the morning after pill. Any man who can score both Gisele Bundchen and Bar Rafaeli, is a first ballot bachelor hall of famer. And have you seen Erin Heatherton? A Skokie girl done good.

Gus: Please, only Dicaprio eskimo brother, Mike Rosemeyer, cares about him hooking up with Heatherton. Supermodels come and go. They need to hook up with celebrities in order to stay relevant. You know who doesn’t? Other celebrities. Jeter has pulled some of the hottest women, all in their primes. Mariah Carey, in the 90s. When she could still sing and hadn’t aged twenty years in two. This bloated, beat up version is fine for Nick Cannon, but Jeter gets the prime rib.

Take note, Nick Cannon. Jeter tapped your wife when she looked like this.

Take note, Nick Cannon. Jeter tapped your wife when she looked like this.

MASK: Want some celebs, okay. Sienna Miller in 2005, not only did they hook up, but she went out of her way to hook up with him to get back at philandering husband, Jude Miller. This shows what a stud Dicaprio is, Miller could have chosen anyone and she went with him. And how about Blake Lively, she is so hot that I’m 20% convinced she is a collective figment of everyone’s imagination.

Gus: Weak. I could match those with Jordana Brewster, right before the first Fast and Furious movie. Or Joy Enriguez, whom he stole away from A-Rod, bonus points. But I’ll just jump right to the Mt. Rushmore and play my trump card right now. He has the Jessicas, Alba and Biel, Minka Kelly, and Scarlett Johannson on his resume. This is what we call, game, set, and match. No other man on this planet can lay claim to this accomplishment. There is not a better Mt. Rushmore of women on anyone’s resume, including Leo’s.

MASK: You’re a star fucker. Sure those women are good looking, but they are overhyped because they are celebs. The supermodels that Leo hook up with may not be as famous, but many are hotter than even those four women. Just look at this slideshow for reference.

Gus: Whatever. Hooking up with a supermodel is as easy for a celebrity as kicking cats. Jeter challenges himself. Take a look at this story for reference.

MASK: The bottom line is that both have amazing success with women, but one has to work out constantly, spend a lot of time with sweaty dudes, and constantly travel to cities like Kansas City and Cleveland. The other gets to travel the world, get first class treatment everywhere he goes, work with attractive actresses, and work with the most talented directors. Leo gets his face plastered on posters around the world and is projected on the big screen playing some of the most memorable characters in film history.

Gus: Jeter may have to work out a lot to compete, but Leo has to constantly alter his mind to get into different characters. He has to go away for months at a time, living out of his trailer on long, arduous film shoots. Jeter, on the other hand, gets to play a game for a living, and he gets to do it New York City. It is a game most people play as a kid, but he gets paid millions of dollars to do it as an adult.

MASK: A game he is forced to retire from at the end of the year due to physical limitations. Athletes careers do not last as long as actors, Dicaprio will be acting for another 40 years while Jeter will only make limited appearances on TV. His fame will slowly fall off.

Gus: First of all, his legacy is set for life. Secondly, he will have the opportunity to get some privacy and have a chance to live a more normal life. The swinging bachelor life is a lot of fun, but after awhile the joy diminishes. Jeter has the opportunity to settle down and live outside the limelight. Dicaprio is forced to be paraded out in front of the American public with every film he makes.



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