1. Vin Baker

Baker had a great NBA career, playing in four All-Star games and earning nearly $100 million. In the 1995-96 and 1996-97 seasons, the power forward scored more than 20 points a game for the Milwaukee Bucks. He could've had even better numbers, but his career was derailed somewhat by struggles with alcoholism. After he retired (or rather, couldn't find a NBA team who would sign him), Baker also squandered his millions and was arrested on a drunk driving charge in 2007.
But Baker turned his life around, and he took the humble approach. In addition to working as a part-time minister at his church, he's a barista at a Starbucks in Providence, Rhode Island. And he was selected by the company for the management track — hopefully he can manage multiple Frappuccino orders better than he managed dealing with Michael Jordan.

2.Steve LArgent

The first superstar—and for a great long while, the only superstar—to suit up for the Seattle Seahawks, Largent was a legend in the Pacific Northwest. When he retired in 1989 after a 14-year career, the wide receiver held records for most career receptions, most receiving yards, and most TD receptions. He was enshrined in the Pro Football Hall of Fame in 1995, the first year he was eligible. And by the time of that honor, Largent was actually a sitting member of Congress.
Yep — in 1994, Largent was part of the "Republican Revolution" that swept into the House of Representatives during the midterm elections, with Largent representing a district in his home state of Oklahoma. Largent left Congress in 2002 to run for governor of the state. He lost to Brad Henry by just 6,300 votes, and moved on to become a lobbyist for the cell phone industry. The jury's still out on whether he supports pretending your football is a phone after you score a touchdown。

3.Shandon Anderson

This versatile forward/guard plugged in holes in the lineup for Utah, Houston, New York, and Miami over a ten-year NBA career that he finished out with an NBA title with Miami in 2006. Also, Anderson had been a vegetarian since the early '90s, but upon retiring, he realized that not only were there not many vegetarian restaurants around, but he didn't know how to cook very well either.
So, he went to culinary school. Several times. First he attended the Living Light Culinary School in California, then the Raw Cooking School (also in California), and then the Natural Gourmet Institute in New York City. In 2010, after completing an internship at the NYC vegan restaurant Candle 79, Anderson opened his open high-end vegan Thai restaurant in Atlanta called Drink Art. (Unfortunately, it closed down in 2014.)

4.Joey Harringson

In 2001, Harrington quarterbacked the Oregon Ducks to one of their most successful seasons ever: an 11-1 record, a win in the Fiesta Bowl, a #2 ranking and, for Harrington, a finalist spot in the Heisman Trophy running. The Detroit Lions drafted him with the #3 pick, thinking he'd be the franchise player to turn around their perpetually poor showings. They were wrong, as is typical of the Lions: Harrington floundered in the NFL and bounced around the league, mostly as a backup, before leaving the turf in 2009.
He then returned to his hometown of Portland and dove into charity work, starting the Joey Harrington Foundation, serving on the board of multiple charities, both funding and serving meals at a homeless shelter and exploring the idea of opening a medical clinic to serve Portland's substantial homeless population. Oh, and he's also an accomplished jazz pianist, just to further drive home that fact that, even as a failed pro athlete, he's very much a winner.

5.Karl MAlone

Karl Malone, member of the 1992 Olympic Dream Team, is the #2 scorer in NBA history, trailing only Kareem Abdul-Jabbar. He's also an incredibly successful, and varied, businessman. He owns an Arby's, a cattle ranch, three Jiffy Lubes, two Burger Kings, a used car lot, a body shop, a real estate company that builds malls, and a deer farm. But his favorite venture of all of it is his Louisiana timber operation. Spanning thousands of acres, he hauls all his own timber, by himself. This is actually something Malone has been interested in for more than 20 years—when he was an active player in the '90s, he ran his own trucking company until it collapsed under financial issues. The Mailman's faring much better as a businessman these days, and now delivers lumber rather than mail, it would seem.