Chances are Ian Desmond regrets a decision or two on the business side of his MLB career. He could be in the midst of a seven-year, $107 million extension with the Washington Nationals, but instead bet on himself and paid for it dearly.

Desmond hit the open market last winter for the first time following a lackluster 2015 campaign, and finding a new home wasn’t easy. Having draft-pick compensation attached to him didn’t help, either.

It got to a point where Desmond, an All-Star shortstop in 2012, settled on a one-year, $8 million at the end of February with the Texas Rangers to play the outfield. You don’t see many shortstops having to do that in advance of their age-30 season to facilitate finding a job.

Unlike the first time, Desmond’s second bet on himself to rebuild value and re-enter free agency the next winter appears to have worked. He turned into the Rangers’ everyday center fielder, hitting .285/.335/.446 with 22 home runs, 21 stolen bases, 86 RBI and 107 runs scored in another All-Star campaign.

A Different Story This Time Around?

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