One thing every guy wants to be labeled as is successful.
How one actually defines that word is pretty transparent, but in sports, success in our book is measured by championships.
With winning comes money, and these old guys have plenty of it—while also proving that they've still got what it takes to have some serious swag.
They may have gray hair and wrinkled skin, but I'd suggest taking notes, because these are the coolest (and richest) old guys in sports.
Net Worth: $14 Million
He might not be one of your favorite announcers, but former head coach Jimmy Johnson is definitely a guy I'd like to drink with.
Johnson proved that when he was caught doing the Dad dance a few years back.
On top of his bottle turning, Johnson's outgoing personality seems like he'd be the perfect guy to have around to pick up the bar tabs and holler at lovely ladies.
Net Worth: $40 Million
Honestly, the only reason why I'm adding six-time Major winner Lee Trevino on this list is because of his cameo in my favorite movie, Happy Gilmore.
Even though Trevino regrets the move to shake his head and remind everyone that "Grizzly Adams did have a beard," he's still a cool dude to me.
Plus, he's been struck by lightning and laughs it off like it's nothing—which takes some serious (golf) balls to do.
Net Worth: $2.5 Billion
Though Mavs owner Mark Cuban might have a loud mouth, he's got one of the largest bank accounts on the planet too.
For his openness and actual passion about his franchise, Cuban is one of my favorites.
If you follow him on Twitter, you can hear all about his crazy life, which sounds like a damn trip if you ask us.
Net Worth: $10.2 Billion
The owner of prestigious Premier League club Chelsea, Roman Abramovich isn't shy about showing-off his wealth.
With a stable of enormous mansions and yachts to compete with other billionaires in the world, he definitely knows how to play hard.
Seeing that his club has succeeded as much on the field as his bank account has—and that he's married to one fine piece in fashion designer Dasha Zhukova—Abramovich is definitely one happy man.
Net Worth: $5.7 Billion
Sure, Heat owner Micky Arison might have had some problems with his Carnival Cruise ships in the past year or so—actually costing him his job—but if you ask him about his success as a team owner, he'll just smile from ear-to-ear.
As the guy who writes the checks to stars like LeBron James and Dwyane Wade, Arison's Heat have won the past two NBA titles, giving him three total since taking over the club in 1995.
We'd say giving up your day job for that is quite the trade off.
Net Worth: $500 Million
Besides being one of the greatest ballers of all-time, Magic Johnson has shown that his infectious personality on the court is quite successful off of it as well.
As the King of Los Angeles, Magic led the Lakers to five NBA championships during the '80's, ending his stylish career as the NBA's leading assist man (since broken), while revolutionizing the point guard position.
He's now part owner of the Dodgers, is an analyst for ESPN and a huge advocate in philanthropy and other business opportunities.
Net Worth: $50 Million
OK, so there are a hell of a lot of people who don't like NBA commissioner David Stern—as if the boos he gets at nearly every public appearance didn't prove that.
But after running the league for nearly 30 years, he's helped the game evolve into something that very few could have envisioned it being back when he started his post.
Stern's reign began in 1984 with the likes of Hakeem Olajuwon, Michael Jordan and Charles Barkley, and will end next February with guys like LeBron James and Kevin Durant as the global icons he helped put on display for the league.
Net Worth: $2.7 Billion
As the owner of the Dallas Cowboys, Jerry Jones has single-handedly run the franchise under with the term "America's Team" solely in his skull.
Whether true or not, Jones' confidence is what makes him so appealing, as he truly loves the moniker "Everything's Bigger in Texas," as he proved with his $1.2 billion stadium.
And in case you doubted his power, he has cats cleaning his glasses for him, so there's always that little piece of spoilage.
Net Worth: $80 Million
In order to persuade three future Hall of Famers to sacrifice both money and stats in exchange for titles, a dude has to have some serious pull.
That's exactly what Pat Riley has then, because he was able to make it happen for Heat fans back in 2010 by getting LeBron James and Chris Bosh to play alongside Dwyane Wade in South Beach.
In addition to winning an NBA title as a player (Lakers, 1972) and five as a head coach, Riley's efforts in getting the "Big 3" together have led to the Heat capturing the past two NBA titles.
And he still has some serious style.
Net Worth: $45 Million
If you asked a number of NFL players, they'd probably tell you they don't like the dictatorship of commissioner Roger Goodell.
But, save for a few, they have to respect what the guy has done for the sport.
Helping football evolve into a more global entity, Goodell's effect can be seen both internationally, in the rulebook and in holding players accountable for their actions.
If that's not influential and cool enough, his bro hugs on draft night should be enough to convince you he's got some cred.
Net Worth: $200 Million
Besides being a nine-time Major champ, golfing legend Gary Player has managed to be one of the coolest dudes to ever play the links.
We don't want to see it, but there's no denying it's a cool (and bold) move for "Mr. Fitness".
New Worth: $18 Million
Is it just me, or does former Brazilian soccer stud Pele always have that trademark smile plastered across his face?
Like seriously, I've never seen him unhappy.
Can anyone blame him though?
Regarded as the greatest player to ever wear a soccer jersey, the three-time FIFA World Cup winner achieved numerous honors during his playing career that catapulted him into the ambassador he is for the game now.
His involvement in various philanthropic ventures only adds to his coolness factor.
Net Worth: $10 Million
Want to know what a true winner really is?
Just talk to former Celtics great Bill Russell, whose 11 NBA titles in 13 seasons shows that he absolutely dominated the hardwood.
As the ultimate champion, the NBA honored Russell by naming the Finals MVP after him back in 2009, showing that the award is both for play in the postseason, as well as the dignity, class and respect that Russell has.
Net Worth: $675 Million
You've got to wear pink to drink, right?
If that's the case, golfer Arnold Palmer does it just fine, rocking that pastel-colored shirt in this picture—I'll forgive him for the bucket hat.
Net Worth: $2.3 Billion
Since taking over ownership of the team over two decades ago, the Patriots' Robert Kraft has proven that he's one of the most influential and successful owners in all of sports.
Not only has he paved the way (with a little help from guys named Belichick and Brady) for three Super Bowl titles, but he's made the organization the premier franchise in the NFL, and possibly all sports.
If that's not enough to prove he's cool, the dude founded the MLS' New England Revolution. Kraft is also huge when it comes to philanthropy and, oh yeah, is dating a smokin' hot model named Ricki Noel Lander, who is 40 years his minor.
Net Worth: $45 Million
Former NBA head coach Phil Jackson might not have the deep pockets that some of the other guys on this list do, but is there any doubt he's still a rich, cool dude?
First, he's won the most titles of any coach in NBA history (11), while also adding two from his playing days.
Second, he's engaged to Executive owner of the Lakers, Jeanie Buss, meaning he's got quite the chip in his pocket on all basketball-related decisions for the storied franchise.
Lastly, and my personal favorite, he's on Twitter, and has the best avatar on the planet, rubbing his 11 rings in everyone's faces.