He was soon rubbing shoulders with Larry O'Brien, the former NBA commissioner, and later met current NBA commissioner David Stern, who eventually hired him to be his special assistant. A career in sports was born, and Postolos has been a fixture in the Houston sports scene for more than a decade.
Postolos has traded the thump of the basketball for the crack of a baseball bat. The 48-year-old Harvard Law School graduate is in the early stages of his new role as the Astros president and CEO, responsible for the day-to-day operations of the team under a new ownership group led by Houston businessman Jim Crane.
"I'm a big fan of baseball and have been all my life," said Postolos, who's from San Antonio. "It's a great game. I love the way it appeals to everyone. Really, so many people come to a ballpark every year, and it's a huge portion of the population you reach. I love that about the sport. I love the tradition."
Postolos is no stranger to Minute Maid Park, considering he says it's been the favorite entertainment destination of his 16-year-old son, Lucas.
"There's nothing more fun for me than going to the game with him, and we've been to ballparks around the country together," he said. "That's one of the best things about the sport, the way it lends itself to parents and children and grandparents and children enjoying the game together. I've had that same experience."
Postolos has his work cut out for him in Houston, where the Astros endured a franchise-record 106 losses this past season as they try to rebuild. It didn't take long for Postolos and Crane to begin to make changes, announcing Sunday that longtime president of baseball operations Tal Smith and general manager Ed Wade had been dismissed.
Much of Postolos' time these days has been spent trying to line up candidates to interview for the vacant GM spot and prepare for the Winter Meetings in Dallas, which start on Monday. These are difficult tasks, to be sure, but Crane has complete confidence in his right-hand man.
"He's been there with me along the way and knows sports well," Crane said.
Postolos was COO of the NBA's Houston Rockets for four years and president and CEO for four years, and he was instrumental in the development of the Toyota Center. He was also behind Comcast SportsNet Houston, a regional sports network formed in partnership with the Astros and Rockets that will begin next year.
Postolos left the Rockets in 2006 and started a company that helps acquire sports franchises. He and Crane attempted to land the Rangers and Cubs before coming through on their second attempt to purchase the Astros -- a $610 million deal that hinged on a 2013 move to the American League West.
"In terms of getting my arms around the business of baseball, Jim and I have been looking at baseball for over four years," Postolos said. "We've had a number of acquisitions where we've come close, so we've studied a number of different organizations and the industry. We've seen different managements and strengths and weaknesses of different organizations. We've been at it a long time."
And the work is just beginning. Upon buying the team, Crane said the payroll will go down before it goes up, as the Astros remain committed to getting competitive on the field through development of the young prospects they've acquired.
Crane and Postolos studied the baseball operations of the Cubs and Rangers closely when they were bidding on those franchises. They met with former Cubs GM Jim Hendry and Cubs president of business operations Crane Kenney, as well as Rangers GM Jon Daniels and club president Nolan Ryan on multiple occasions.
There's no denying Postolos has done his homework in anticipation of getting the keys to the Astros.
"It's something we're very excited to begin," he said. "You're always going to start wherever you are. We have a good understanding of both where the Major League club is and where the farm system is. We know we have to improve the system. Jim has talked about that repeatedly. We've watched the franchises that have made significant runs and how they've put the pieces together."
Postolos is confident the Astros can return to prominence.
"We look at Houston as a situation that has potential to be a dominant team," he said. "Same thing in other sports here. It's a great market, and the key is to get in position to have a good business model. You want to get into position where you know you're on the way up and the market understands and you're making decisions every day to move the franchise forward. There's no reason to look back."