Sink into comfortable obscurity.
To be fair, Shaq makes a bigger pain in the ass of himself on the same sports analysis program.
Shaq undoubtedly made a lot of money from his basketball contracts over the course of his career, but I sometimes wonder if he’d invested poorly (or had been taken advantage of by agents or managers), because he appears in so many ads now, for just about anything. Either he really likes working, or he needs the money.
He actually has made quite a bit of money in investments. He owns some Krispy Kremes (though his most famous store burned down recently) and Papa John’s in Atlanta. He just likes working and making money.
And apparently a lot of 5 Guys restaurants:
The OP talks about having hundreds of millions of dollars. That’s enough that you could invest in hedge funds, venture capital or private equity. Some of these supposedly make really high returns, but they’re also expensive. Hedge funds, for instance, take two percent annually and twenty percent of profits. You might be better off just passively investing in index funds. Buy a couple of houses someplace nice and enjoy retired life why you’re relatively young.
I’m loud, obnoxious, boorish and think I know a lot more than I really do and share my “knowledge” with others whether they want to hear it or not, so retired I’d be a shoo-in for color commentary on ESPN. Or The Ocho.
I’m glad to learn that that’s the situation, even if he makes a lot of goofy ads. 
I don’t think Stephen A. Smith or Colin Cowherd actually played any pro sports.
This is something I’ve wondered. With jerks like Deion Sanders, Charles Barkley, or Shannon Sharpe, at least they busted their chops in the big leagues so they have the credentials. But just what exactly makes someone like Skip Bayless or Stephen A. Smith’s opinion any more qualified than yours or mine?
Bayless and Smith were both sports journalists/columnists for various newspapers before winding up on TV. (And, Smith played college basketball.) But, otherwise, the only thing that makes their opinion more “qualified” is that someone at ESPN or FS1 is willing to pay them a lot of money to bloviate on TV every day.
I’d invest in boring things, buy a couple properties near my family and in places I want to visit a lot. And travel.
Decent change I’d go back to school.
The same reason why anyone is invited on TV to talk about something: the promoter of the program thinks that what they have to say is worthwhile. Presumably they say things that at least sound good, and hopefully make predictions that tend to work out. I’d much rather hear people that have genuine insight into a sport than a random player who was just gifted athletically.
IIRC, both Bayless and Smith were well respected newspaper journalists (Bayless more than Smith). But like with cable news, they were basically told that in order to get ratings on 24/7 sports networks you need to get into the hot takes business. Bayless originally was on ESPN in The Sports Reporters show hosted by Dick Shaap. He was very different back then.
So it’s kind of a don’t hate the player, hate the game sort of situation.
Do I have to pick one? Can’t I do both? 
Go into politics?
Worked for this guy.
And this guy
In the U.S., some successful athletes who later went into politics include:
- Bill Bradley (basketball, then U.S. Senator)
- Jim Bunning (baseball, then U.S. Congressman and Senator)
- Jack Kemp (football, then U.S. Congressman and Cabinet secretary)
- Steve Largent (football, then U.S. Congressman)
Bradley, Bunning, and Largent are all in their respective sports’ Halls of Fame.
Why not Kemp? (Doles running mate if memory serves)
Yes, Kemp was Dole’s VP candidate in 1996. As to why he’s not in the Hall of Fame – it’s a good question. He was one of the AFL’s best quarterbacks throughout that league’s existence: he won two AFL titles (and played in five championship games), was a five-time All-AFL selection, and was the league’s MVP in '65.
He’s probably one of the best quarterbacks not in the Hall, and I think one could argue the case that he should be in. It’s possible that his career was overshadowed by other successful AFL quarterbacks who did get elected to the Hall, including Len Dawson, George Blanda, and Joe Namath.
Kemp had a relatively short career comparatively to other big AFL QBs which worked against him.
Is there any other quarter back in American football who has won two titles and hasn’t gotten in?