Jimmy Rollins: The Hardest Decision Is Always The Last One

Feb 25, 2016; Glendale, AZ, USA; Chicago White Sox shortstop Jimmy Rollins (7) looks on during a workout at Camelback Ranch Practice Fields. Mandatory Credit: Joe Camporeale-USA TODAY Sports
Feb 25, 2016; Glendale, AZ, USA; Chicago White Sox shortstop Jimmy Rollins (7) looks on during a workout at Camelback Ranch Practice Fields. Mandatory Credit: Joe Camporeale-USA TODAY Sports /

Jimmy Rollins can probably tell you that beyond deciding whether to swing on a 3-0 count, picking an agent, or even deciding which offer to accept as a free agent, the most challenging decision facing a major league ball player is the one that is usually the last one that occurs over the course of his career, and that’s when to “hang ’em up”. Stay too long and you’ll regret it. Get out too soon and you’ll regret it. Let baseball decide for you so you reach a point where nobody wants you, and you’ll regret it. So, how do players cope with this anomaly…….

Ken Rosenthal , the noted writer of all things baseball, recently spent some time with Jimmy Rollins , who has spent 17 years of his adult life playing baseball, and is desperately trying to find a way to play season number 18,  as a 38 year old shortstop to boot.

Naturally, the first question Rosenthal asked him was, “Why?”.

Jimmy Rollins: It’s Harder Getting Out Than Getting In

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And as you read through Rosenthal’s story, it quickly becomes clear that there is no why for Jimmy Rollins. And all there is, is the feeling from him that we’ll never understand, no matter how hard we try. Because it’s about one more year, one more Championship like the one he won a long time ago in 2008. And it’s about the comraderie among his peers, the ones in the fraternity who look at him and say to themselves, “Someday, I’m going to be him. But that’s tomorrow, how about we shag some fly balls now?”. Anything but having to think that the end is coming.

And for nearly all players, this is the one time when it really isn’t about the money because you’ve already made a bucketful and more than you ever would have dreamed of (Rollins, for example, has made $100 million in the game). No, it’s about all those intangibles that are difficult to surrender to.

And over the course of time, we have seen the best and the worst when it comes to retirement. And it is still painful to recall, for example, Willie Mays lumbering around in the Mets outfield in his 40’s, until he finally decided to quit after Game 2 of the 1973 World Series. Or more recently, watching Ryan Howard struggling through the final years of his contract with the Phillies, until the final day of his career when he would tell the assembled crowd and all of Philadelphia, “It will be with me forever”.

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A few though get out while the gettin’s good. Jeter gets that bloop single to drive in the winning run in his last at bat (video here ). Or Ted Williams hitting an unbelievable home run in his last at bat (video here ). And then of course, there’s the monumental season that David Ortiz just completed (video highlights here ).

But for every one of those stories, there are probably ten more that display the less glorious side of the game. And it’s not just relegated to players at the major league level. When I was writing a column called Reflections On Baseball, I did a piece on a player named Chase Lambin, who spent 13 years in the minor leagues without having a single at bat in the majors, before retiring last season to take a coaching position with the Mariners. It gets in your blood and it becomes part of your DNA.

And that’s maybe why Jimmy Rollins fumbles around when asked a simple question by Rosenthal, “Why, Jimmy?” Why would you agree to a minor league deal with the San Francisco Giants after all you have accomplished in the game.

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Maybe by now though, we’ve have a better understanding of what Jimmy Rollins is thinking, even if he can’t explain it himself.