Ryan is the president of the Texas Rangers, a position he has held since 2008. Just two months ago, he was part of the ownership group that purchased the team.
And now? Ryan is back in the World Series for the first time since 1969, when he was an up-and-coming starter/reliever for the New York Mets. He pitched once in that Fall Classic, firing 2 1/3 innings of shutout relief against the Orioles.
"It seems like another lifetime," said Ryan. "It really is exciting. If you had told me two or three years ago I'd be standing here today, I would have thought that was impossible. I wouldn't have thought this was realistic. This is one of those magical years. This team has heart and never thinks they're out of it. It's rewarding to be associated with it."
Between World Series appearances, all Ryan did was develop into a baseball icon. One of the best pitchers to ever step on a mound, Ryan fired seven no-hitters, the most in history. By the time he retired in 1993, at the age of 46, he had 5,714 strikeouts, a record that might never be broken.
Since that last taste of the Fall Classic, Ryan moved from the Mets to the Angels to the Astros to the Rangers -- and eventually back to the Rangers in his current capacity.
The last time Ryan lived in a state besides Texas was 1979 -- his last year with the Angels. So it was only fitting that it was Jackie Autry -- the widow of music star and former Angels owner Gene Autry -- who handed Ryan that trophy on Friday evening.
Yes, a whole lot has happened to Ryan since the last time he was part of a World Series team.
When Ryan came back to the Rangers, he wanted to help change the culture of the organization and develop a winning atmosphere, particularly on the pitching side. Clearly, he has succeeded in that mission.
"He's the type of guy, he helped put this together," said Colby Lewis, who earned the win in Game 6. "He had a lot of faith in us. The table was set. We just had to go out and do it."
Ryan could only watch. And his stomach churned while he did. After Ryan played for that championship team in New York at the age of 22, he played for four postseason entries (1979 Angels, 1980 Astros, 1981 Astros, 1986 Astros) that fell short of the World Series.
"Yeah, I was nervous," Ryan said. "When you think of how important this is and what it means to our organization and Texas and the Metroplex ... you get so close. I've been involved in a lot of postseason play where we never get to the World Series. I know how hard it is and I know what can happen. So, naturally, you worry about those things, even though you have no control over them."
How special is it to see Ryan back with a World Series team?
"Words can't explain it," said pitching coach Mike Maddux. "He'd have to answer that."
Ryan did his best to share his emotions.
"It's so exciting and just a different feeling at this point and time in my life and to be associated with a group of players like this and an organization, it's such a team effort and an organizational effort," Ryan said. "It's just a special feeling. The best thing I can relate it to is watching your children be successful."