But his connection to the team was really renewed this season, as his son, Reid, was hired to be Astros president on May 17.
Reid is a gregarious figure for the organization, but it's still a new job, one Nolan says is becoming second nature to his son.
"With Reid, it's like anybody coming into a new position and never holding it before. It's a real learning curve," Ryan said. "He has such an enthusiasm, a passion for baseball, that I think it's been a real good fit for him. The challenge of selling his home, changing towns, of moving here and getting his kids in school, just added to the learning curve with the ballclub.
"I think he's handled it really well. If you asked him today about his comfort level and confidence, it's much higher than it was a month ago."
Ryan also spoke about the Astros' recent bullpen woes, which his team took advantage of to the tune of six late runs in a 9-5 win over Houston on Friday night.
"I can tell you, the emphasis on bullpens have changed in my career," he said. "When I went through a rebuilding process with the Angels, we had an inexperienced bullpen, but they were used totally different. You went with your starting pitchers until the end of games."
Two Astros relievers, Jorge De Leon and Kevin Chapman, made their Major League debuts on Friday, and seven of Houston's nine bullpen arms are rookies. The Astros' bullpen has an ERA of 7.46 since June 23 and has blown five of six save opportunities during the last two weeks.
"The emphasis on bullpens now is higher than ever before," Ryan said. "And I think that the Astros are asking a lot of young kids that don't have a lot of experience to step on a Major League stage, and there's challenges there. With young players, there's so much inconsistency, and I think that's what they're seeing.
"At the end of the year, their baseball department and [Houston manager] Bo Porter will have a better feel for what areas they'll need to strengthen."