But no one was prepared for the one-year, $US8 million ($NZ12.1 million) deal he signed with the Texas Rangers this weekend.
It is a tiny contract for a player who won multiple Silver Slugger Awards and averaged a Wins Above Replacement (WAR) of 4.4 in the three years before 2015.
Even worse, the Rangers are moving Desmond to left field, where his value is immediately undercut.
So, to sum up: Ian Desmond basically lost nine figures - $NZ151.7 million - betting on himself.
Now he is searching for the positives.
"This is a new chapter," Desmond was quoted as saying by the Dallas Morning News.
"I'm going to embrace the challenge."
Former Washington Nationals general manager Jim Bowden said on MLB Network Radio he'd "never seen a worse contract for a player".
"That's a shocking number," Bowden said.
"What a great job by (Texas Rangers general manager) Jon Daniels to hang around long enough to get Desmond for one year at eight.
"So he went from 107 million to losing 99 million over the last 12 months? You want to talk about a humbling sport?"
Perhaps Desmond turned down the offer because he'd seen the astronomical figures earnt by former Colorado Rockies player Troy Tulowitzki ($NZ242.7 million) and Texas' Elvis Andrus ($NZ182 million) in their new contract dealings at the time, and he thought he could match that.
But the 30-year-old's biggest problem was that instead of maintaining his impeccable standard, he only got worse.