Now 64, he's done it for the first time as a baseball executive in back-to-back years. His club's 15-5 drubbing of the Tigers in Game 6 of the AL Championship Series attests to that. The Rangers won the best-of-seven series, four games to two, and what's ahead of them is a highly anticipated second shot at a World Series title, beginning on Wednesday night in either St. Louis or Milwaukee.
The long road for Ryan began as a skinny, hard-throwing kid from Alvin, Texas, who went on to set a Major League record by tossing 5,714 strikeouts. But the long road for these Rangers began late in the evening of this past Nov. 1 after the Giants eliminated them in five World Series games.
In the same clubhouse where they celebrated on Saturday night, the club sat around digesting what had just happened: Edgar Renteria's stunning seventh-inning, three-run homer off Cliff Lee. Brian Wilson's punchout of Nelson Cruz to end a dream season in which the Rangers ascended to the World Series for the first time in their history.
It was then, said Rangers general manager Jon Daniels while standing on the mound not long after the game had ended on Saturday night, that this club made a commitment to do it all over again.
"The guys were sitting around trying to digest what had happened to them and I got a sense that was instantaneous," he said. "They had already shifted their focus to next year. I mean, most of those guys are back. We didn't have a lot of turnover. You saw it. They were focused all year long."
As tough as it is to repeat in the Majors today, the Rangers know that they still have the toughest assignment still ahead of them. They are the first AL team to play in the World Series in back-to-back seasons since the Yankees did it four times in a row from 1998-2001. No AL team has lost the Fall Classic in consecutive years since the Yankees of 1963-64.
In between, the Dodgers of 1977-78 and the Braves of 1991-92 were the only National League teams to do it. And now the Rangers will be stepping up to the plate, trying to complete the job that last year they failed to accomplish.
"All of this is hard work, but it's fun work," said Rangers center fielder Josh Hamilton. "This is where we want to be. It's hard to repeat, there's no doubt about it. You have a lot of teams that gear up to try to beat you. It says a lot about our guys and their determination. They want to be winners."
It was only a little more than a year ago that the Rangers came out of bankruptcy and were sold at a court auction to the current ownership group that is headed by Ryan, who now holds the club's vote at all Major League meetings.
The franchise has become Commissioner Bud Selig's poster team for competitive balance. With a player payroll of $92.1 million, they are ranked 13th in the big leagues overall and seventh in the AL. It should be noted that the nine top paying teams in MLB this year, including the Yankees, Red Sox and Cubs, either didn't make it the playoffs or were eliminated in the first round.
Last year, as the Rangers struggled for financial stability, they went to the World Series with a payroll of $55.2 million, 27th out of the 30 MLB teams.
Thus, success at this level comes with a sizable commitment from ownership all the way down to the equipment manager.
"It's amazing and exciting," Ryan said. "The hardest thing to do is repeat. But our guys -- I saw it in Spring Training -- they were determined to get another shot at the World Series and being world champions. They had that attitude all year. And it showed."
Now they have a rare opportunity. Another shot at it. A luxury Ryan never had as a player. They have the AL championship trophy in hand, but that's only for those who finish second best. Ryan said he doesn't wear last year's World Series ring. It's home in a locked box. He's determined that will change.
"Oh, there's no doubt that the hard work is still ahead of us," he acknowledged. "We haven't finished what we set out to do. We have to win four more games."