The 20 Most Excruciating Hypothetical Questions in Sports

Dan Carson@@DrCarson73Trending Lead WriterMarch 26, 2013

The 20 Most Excruciating Hypothetical Questions in Sports

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    Few activities are more entertaining than arguing over a good hypothetical situation with friends.

    Who would win a fight: Bruce Lee or a Kodiak bear? Which would you rather get locked in a cage with: a starving panther or a talkative Skip Bayless?

    Countless hours have been spent arguing these kind of hypothetical points, and perhaps the most entertaining questions/scenarios involve the uber-competitive world of sports. 

    The following are 20 of the most grueling, strange and difficult quandaries facing mankind today. Some are serious, others are downright foolish, but they all must be approached with a sense of humor and a willingness to tackle weird and painful scenarios with cold and (somewhat) logical reasoning.

    If you’re ready, click on. And may the strongest/weirdest fan win.

1. Win the NIT or Lose Early in the NCAA?

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    Would you rather: win the NIT tournament, or lose in the second round of the NCAA tournament to Lehigh?

    Just thinking about this one burns, but there are positives to both scenarios despite the cancerous amounts of buzzkill inherent in each occurrence.

2. The Ray Lewis Quandary

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    Would you: get a barbed-wire tattoo laced with Skip Bayless quotes around your arm if it would save the world from a Ray Lewis comeback in the NFL?

    Some things to consider: Lewis’ comeback would be one of the most covered sports events of all time, and it would involve winning the 2014 Super Bowl amid a swirling vortex of PED rumors involving “mastodon powders.”

    Would that be worth getting a barbed-wire band with the words “Blake Griffin didn’t even jump that high” woven throughout?

3. Fight: Mike Tyson or John Rocker?

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    Would you rather: fight Mike Tyson in a boxing ring on live television? Or tangle with former Atlanta Braves psycho John Rocker in a dark alleyway? 

    Note: Both are in the craziest prime of their careers. And both overheard you talking about having a superior education compared to theirs.

4. Taking One for the Home Team

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    Would you: work once a week in the stadium of your team’s biggest rival for a season, picking up their garbage, working the turnstile and silently enduring their drunken trash-talking, if it meant your team would win the national championship/title game/tournament cup?

    There’s nothing worse than having to endure the drunken, ignorant smack-talking of rival fans—except doing it in silence, as you clean chili dog from beneath the seats in their crap hole stadium.

5. The Problems of Parenting

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    Would you rather: your child grow up to be the greatest curler to ever broom the ice? Or the goofiest wrestler in the WWE?

    Real parents have to say “Whatever makes my child happy is what he should do.” However, hypothetical parents on an Internet site have to choose between a future of ice sweeping or mankinis.

6. Knuckleball or Fastball?

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    Who would you rather have pitching for your team in Game 7 of the World Series?: R.A. Dickey on a smoking hot streak, throwing quivering knuckleballs? Or Randy Johnson (in his prime) raining down 100+ mph bird-killers? 

    Randy Johnson was one of the best pitchers ever, but R.A. Dickey’s throws one of the most dominant pitches baseball has ever seen when he’s on.

7. Canning Gary Bettman

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    Would you: take a slapshot to the butt if it doing so meant Gary Bettman retired from his position as NHL Commissioner?

    No pants. Bare bottom. And the player shooting the puck is Zdeno Chara, who cranks a healthy 108 mph slap shot.

8. Take a Free Kick to the Pills, or Watch This Commercial?

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    Would you rather: take a Roberto Carlos free kick to the groin just once, or have to watch this Armani commercial featuring Cristiano Ronaldo every time you opened your Internet browser. 

    They’re both excruciatingly miserable, and I don’t know which one would cause more damage in the long run.

9. Listen to All of Manti Te'o's Hoax Calls for a National Title?

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    Would you: listen to all of Manti Te’o’s phone calls with hoaxer Ronaiah Tuiasosopo if it meant your team won the BCS championship?

    Keep in mind, you’re listening to every single hoax-y one of them. And in case you wanted to know, here’s a sample of what they might sound like.

10. Taming the Black Mamba

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    Would You: handle a live black mamba in order to never hear another word on SportsCenter about Kobe Bryant’s passive-aggressive relationship with Dwight Howard for the rest of the season?

    No gloves. No snake stick. 

    I’m talking about a bare-handed snake slapping here. But since the season is well underway, you get to choose whether the mamba is in a box or on open ground. And you only have to tag it and say “You’re it.”

11. The King, His Airness or the Diesel?

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    If you were the Miami Heat, would you: rather have current LeBron James on your team? Or Michael Jordan in his prime (1986-1990-ish)? Or would you rather replace Shaquille O’Neal in his prime (1993-1997-ish)?

    We all know LeBron James is playing some of the most dominant basketball ever played right now, but that guy Michael Jordan wasn’t too bad, either.

    Some things to consider—you have Dwyane Wade on your team. Not exactly a terrible scorer, ball handler and all-around competitor. 

    You also have Chris Bosh on your team. So there’s that.

12. The Next UCLA Coach: Tubby Smith or Andy Enfield?

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    If you were the athletic director at UCLA, would you rather: replace Ben Howland with FGCU's Andy Enfield or Minnesota's Tubby Smith as the head coach of your basketball program?

    Do you like the flavor of the minute, or a guy with proven staying power?

    Tubby has a long, distinguished track record as a coach in the NCAA. He has an NCAA Championship in his pocket (1998) and was fired Monday after going 124-81 in six years as head coach of the University of Minnesota. That’s a .610 winning percentage in the Big Ten, and certainly nothing to scoff at.

    Enfield, on the other hand, is red hot right now. In two years he has turned Florida Gulf Coast University into an NCAA tournament threat and has had previous success assistant coaching in the NBA and at Florida State University.

13. Curing the Curse

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    Would you rather: eat a whole, uncooked goat to cure your team’s curse and win a World Series?

    If it meant curing the Curse of the Billy Goat, or any other baseball demons your team may have and winning the World Series, would you chow down a raw goat? 

    You wouldn’t have to eat the hooves or the horns, of course. We’re not animals.

    Those would be ground up into a smoothie and drank through a silly straw.

14. A Dairy Important Dilemma

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    Would You: give up cheese for the entirety of the college basketball season if it meant your team not losing to godawful, motherloving Wisconsin? 

    To everyone else they’re a middle of the pack team led by a mole-faced carrot king, but as an Indiana basketball fan, Mike Brusewitz and the Badgers are my personal hell-born Kryptonite. 

    Their deadfish style of basketball destroyed my homeworld and knocked my team out the Big Ten Tournament, forcing me to adopt the same superstitious respect for Wisconsin basketball that I have for my girlfriend’s pet bird.  

    On paper I have all the advantages, but when it gets out of the cage with me in the room, it goes straight for my eyes and I scream like a little whipping boy.

15. Sit in Average Seats or the Best Seats with a Catch?

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    Would you rather: sit in your normal seats at a game? Or sit front row/court side/owner’s booth at any sporting event you ever desired to attend—but you’re not allowed to eat, drink or use the bathroom for the entire contest.

    I’ve tried to think all the angles on this one, but it’s just a cruel, terrible proposition. That is, unless you're sitting courtside with Arrested Development's Will Arnett.

16. Jadaveon Clowney Hit or DeAndre Jordan Dunk?

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    What would you rather watch: POV footage of Jadaveon Clowney’s monster hit taken from inside Vincent Smith’s helmet? Or POV footage of DeAndre Jordan’s thunder dunk on Brandon Knight?

    What would you rather see: Clowney coming at you like a metro train or the saucer-size eyes of Brandon Knight vanishing beneath your mighty dunkitude. 

    Either way, you can’t really lose.

17. To PED? or Not to PED?

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    Would you rather: use PEDs and become one of the greatest players of all time in your respective sport without ever being caught? Or choose not to use PEDs and be a benchwarmer on a team of stars your entire career?

    It’s a question of conscience, and probably a more difficult proposition to hash out than most people would like to admit.

18. Attend the Longest Cricket Match Ever, or the Longest Stand-Up Ever?

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    Would you rather: watch the world’s longest cricket match (105 hours) in an air-conditioned, catered booth? Or watch Dane Cook re-performing the world’s longest stand-up routine (seven hours) with an Irish brogue in a hot boiler room under a Hardee’s? 

    As mentioned before, the booth would be nice and comfy, featuring all the snackeroos and beverages you could want. Dane Cook, one the other hand, would be speaking in a  bad Irish accent and doing a set about anything that pops into his head.

19. Let Your Daughter Be a Ring Girl for Tickets?

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    Would you: let your daughter be a ring girl for a Mayweather-Pacquiao boxing match if it got you ringside tickets?

    First off, we’re assuming your daughter wants to be a ring girl in this scenario. We’re not monsters.

    Second off, this one is dripping with all kinds of awkward funk.

20. The Best of All Photobombs?

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    Who would you rather photobomb: Tiger Woods during his first green jacket ceremony at The Masters? Or Dallas Cowboys owner Jerry Jones on the giant screen at Cowboys Stadium? 

    Photobombing Woods’ green jacket would be a moment in history no one would ever forget. But photobombing one of the grumpiest looking owners in NFL history on one of the biggest screens in the world isn’t anything to scoff at.