Professional athletes definitely have it made, don't they?

Not only do they play a sport for a living, but when they finally do call it quits—typically around the age of 30—they've often made some serious money, allowing them the financial freedom to do as they please.

While we've seen cases of athletes going flat broke after playing, others have been able to keep up their lifestyles, showing us that their retirements are way cooler than ours will ever be.

20. Dave Whelan

Though Dave Whelan didn't have a lengthy career thanks to a brutal knee injury in 1960, the former Blackburn defender took the £400 the club gave him after his injury and told him to basically, "Bug off."

With help from that little "investment," he was able to build multiple businesses and sell them for millions of British pounds, allowing him to purchase his hometown club, Wigan Athletic.

He may be from Britain, but he's the epitome of the "American Dream."

19. Kareem Abdul-Jabbar

Kareem Abdul-Jabbar might be the greatest scorer in NBA history, but he's had a pretty darn successful career off the hardwood, too.

It started with some cameos in a couple movies and has expanded to a couple other roles over the years.

He's due to take the plunge into the water in the new reality show Splash, which should be extremely awkward for the seven-footer to try.

18. Pele

When people say the name Pele, it's usually prior to a conversation about the greatest soccer player to ever live.

But even after the Brazilian player won three World Cup titles—actually playing in two finals—he became even more popular after his career ended.

He's an ambassador for international football and has built an empire around various endorsements and speaking events.

17. Jamal Mashburn

Success means different things to different people, but regardless of your definition, we can probably all agree that Jamal Mashburn  achieved it.

After an NBA playing career that spanned 11 years and earned over $75 million in salary, he's become a poster boy for exactly what athletes should do once ending their playing days are over, building an empire in various business ventures.

16. Dennis Rodman

We all remember "The Worm", Dennis Rodman, for being a little out there and extremely flamboyant during his NBA Hall of Fame basketball career, but ever since calling it quits, he's been able to build off that personality.

He may have gone broke—never a good look—but he'll most likely always have a career in reality TV because of his different ways of doing things.

And who knows, with his recent trip to North Korea, maybe there's a bigger role for Rodman than any of us know?

15. Warren Sapp

Thanks to Warren Sapp's loud mouth during his playing career, he's been able to land himself a pretty lucrative job with the NFL Network.

The massive former DT has caught news lately for his diss of Pats' head coach Bill Belichick, only proving that he just can't help but sharing his opinion on things.

14. Nolan Ryan

During his pitching career, Nolan Ryan was one of the most feared pitchers an opposing batter could face.

As a front office executive for one of his former teams, the Rangers, he has proven to build the organization into one of the most feared in the major leagues.

He may be catching some heat lately on defining his role, but the guy's a retired millionaire and Hall of Famer, so we say let him do what he wants!

13. Charles Barkley

Charles Barkley is one of the best personalities on television, offering his hilarious garb on TNT broadcasts to help entertain us.

He's been with the network since 2000, which has helped him build quite the rep with co-hosts Shaq, Kenny Smith and Ernie Johnson.

It may not be basketball, but we'd say he's enjoying what he's doing every day.

12. Terry Bradshaw

Terry Bradshaw might be one of the most annoying announcers in sports, but he gets paid a lot to be that way, so we're sure he doesn't give a damn.

On top of his broadcasting career, the four-time Super Bowl champ has had a number of endorsement deals and has one of the hottest sports daughters in history, country singer Rachel Bradshaw.

11. Deion Sanders

While growing-up, Deion Sander—"Prime Time"—was the definition of everything people hated in sports.

He was cocky, brash and successful—and made sure everyone knew it.

Though the Hall of Fame DB may have grown up, he's still able to show some of those same traits as a co-host at the NFL Network, in addition to a number of endorsement deals that help him get paid quite nicely.

10. Michael Phelps

Michael Phelps may be new to this list, but make no mistake, the greatest Olympian in history has gotten quite comfortable outside of the pool.

At just 27 years old, he has an entire life to live in luxury thanks to his accomplishments in the pool, which includes a spot on the Golf Channel show The Haney Project, which should help him improve in one of his other sporting passions.

9. Chad Ochocinco

With No. 85, Chad Ochocinco, currently out of the NFL, we're going to go ahead and put him under the retired category—though he'd probably jump at the chance to play again should a team come calling.

In the year since he last played, Ochocinco has remained extremely active on his Twitter account, while still staying in the public eye by doing pretty much the same things that made him a celebrity in the first place—being loud and visible anywhere he can.

And who knows, maybe he'll make a comeback on reality TV if the gridiron thing really is over? 

8. Dwayne "The Rock" Johnson

We're not sure if it's a good or bad thing that former WWE Superstar Dwayne "The Rock" Johnson has randomly become one of the most sought-out action stars in Hollywood.

Regardless of the answer, Johnson is enjoying his run on the silver screen.

Turns out all that acting during his wrestling matches have actually benefited him more than anyone would have ever thought back then.

7. Michael Strahan

Just as former New York Giants defensive end Michael Strahan used to do on the football field in sacking the opposition, he's done the same thing on television.

OK, so he did have that flop of a show a couple years ago, but besides that awful decision, the big man is the host alongside Kelly Ripa every morning, gets his football fix on FOX's NFL Sunday's and is relied heavily on by the league for numerous events.

6. Mike Tyson

"Iron Mike" Tyson may have been brute in the ring, but since removing the gloves, he's shown a more comedic side.

We're sure Tyson would much rather be pummeling someone, but the acting role seems to be a better fit for him—regardless of what he might be on while on set.

5. Thomas "Hollywood" Henderson

Of all people, it might be a little odd to see Thomas "Hollywood" Henderson in our top five, but there are plenty of reasons for him being here.

The former Dallas Cowboys linebacker played in three Super Bowls in his career (winning one)—and admitting to one of the funniest stories ever from an athlete.

The best part though? He won $28 million in the Texas Lottery in 2000, saying he "doesn't do a damn thing," and that he "doesn't start that until after lunch," when asked about what he does everyday since winning the lottery.

Can't argue with him there.

4. Michael Jordan

Michael Jordan's definitely had his ups and downs since leaving the hardwood 10 years ago, but almost rarely does he ever find himself on the losing end.

Let's see here, he's engaged to a model who's 16 years younger than him, still owns his own division of Nike (Jordan Brand) and, oh yeah, is the majority owner of the Charlotte Bobcats.

The 'Cats are arguably the worst team in the NBA—which drives the ultra-competitive Jordan insane—but for even having the chance to own a pro team, Jordan's living the life.

3. John Elway

Former Broncos QB  John Elway has earned quite the reputation as a front office leader thanks to his aggressive moves over the past several years as Denver's Executive VP of Football Operations.

With two Super Bowl wins during his last couple seasons playing, he's hoping to help guide his beloved franchise to even more—while avoiding all the hard hits this time.

2. Magic Johnson

There's really not much more to be said about Magic Johnson that you probably don't already know.

1. He's one of the best point guards in NBA history.
2. Has become a business mogul thanks to numerous opportunities he's started.
3. And finally. he's purchased an ownership stake with the L.A. Dodgers.

He may have been forced to retire from the league due to HIV, but things have been looking pretty good for him ever since he did.

1. Shaquille O'Neal

As a shoutout to a friend of our's who actually helped pitch Shaq's successful TNT segment, "Shaqtin' a Fool," we know firsthand how much the big fella loves retirement.

Shaq's always been a kid at heart, dancing around, singing and trying his hand at everything he can, except now he actually has all the time and money in the world to try them all—while also possessing the personality for it.