Ian Desmond blew $100 million. Don’t feel bad for him.

By now you’ve heard the story: Two years ago, Ian Desmond turned down a reported 7-year, $107 million extension from the Washington Nationals choosing to instead, as we hear so often in sports, "bet on himself" by playing two years and hoping to cash in even more in his 2016 free agency.

Then, after a horrendous contract year, the kind that makes people say "he folded under the pressure," Desmond turned down a qualifying offer from the Nationals for a little under $16 million.

After all that, Desmond waited month after month for a free agent deal, whereupon it became clearer and clearer that his payday wasn’t going to come and he’d probably have to sign a one-year deal to get back in the good graces of the free agency gods. But no one was prepared for the one-year, $8 million deal he signed with the Texas Rangers this weekend, which is an insane lowball for a guy 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. A big-hitting shortstop basically becomes a mediocre-hitting left fielder.

(Photo by Mitchell Layton/Getty Images)

So, to sum up: Ian Desmond basically lost nine figures — NINE FIGURES = $100 MILLION DOLLARS — betting on himself.

There’s a lot to unpack here, so let’s go point-by-point:

1. The first, last and only mistake was turning down $107 million. Obviously it’s easy to rip Desi’s deal in retrospect. He lost nine figures. It doesn’t take a mathematical, business genius such as Donald Trump to figure out what that means. But the problem is that everyone could see this coming from the moment Desmond turned down that nine-figure deal from the Nats. He was playing at his peak. He had received a contract that pretty much put him in line with other players of his ilk. Maybe it wasn’t the most he could have gotten, but it was close enough. 

(Richard Mackson-USA TODAY Sports)

2. The juice wasn’t worth the squeeze. This is the big one and sort of a model of gambling game theory. Desmond risked a guaranteed $107 million to play for free agency with the anticipation that he’d improve his numbers so much that he’d get his contract into the next stratosphere. 

The problem was that Ian Desmond had to realistically ask himself how much better he really could get? The big offer came after the 2013 season, when Desmond hit 20 home runs, had a .784 OPS and an OPS+ of 113, numbers that were down from his All-Star 2012. So, Ian Desmond, coming off a year of decline, figure he’d take a risk and leave $100 million on the table in hope of reversing that trend. 

He did not. His 2014 season was worse than his 2013 which was worse than his 2012. And then his 2015 is best not discussed in polite company.

Taking the risk is great. Betting on yourself shows gumption. But what was the contract ceiling for Ian Desmond? At that point, the $107 million offer would have made him the second-highest paid shortstop in the game. Let’s say he’d broken out as a 28- and 29-year old and hit 33 home runs with an OPS of .880. Let’s say he learned how to take a first pitch and walk every now and again, increased his batting average and struck out less. This was what Desmond could have only realistically hoped for. (If he was banking on tearing it up with 45 homers and Bryce Harper numbers, then that’d just have been unrealistic and stupid.)

(Kim Klement-USA TODAY Sports)

3. How much more would Desmond have received in free agency? He’d have been older, so a seven-year deal might have been off the table, but let’s say for the sake of argument that it wasn’t. What’s Desi going to get in that dream world? $135 million over seven? $150 million? In an era in which Elvis Andrus can get $120 million, that seems about right. 

4. What Ian Desmond did was play a game of high-risk/low-reward. He bet on himself at awful odds. If he played his best, he was only going to increase his yearly salary by 15-20 percent. That’s huge if you’re a regular person, but when you’re a baseball player getting $107 million, it’s less of a hit and the downside is so much greater

5. This doesn’t mean Desmond wasn’t initially lowballed. He certainly didn’t owe the Nationals anything — as he just learned, baseball is a vicious business and you’ll get chewed up and spit out, Silver Slugger awards or not. But Desmond and his representation had to realize that his dream contract wasn’t going to be that different from the offered one. The risk between getting so much better and blowing a possible $30 million was far greater than regressing and blowing $70 million. (Which is the amount most people figured Desmond had blown. A two-year, $30 million contract seemed reasonable this go-round of free agency. The minor leagues aren’t exactly teeming with big hitting shortstops. That $8 million deal is just insulting.)

(Kyle Terada-USA TODAY Sports)

6. It’s not that getting $8 million is cause for charity, just so we’re clear. But having lived in Washington D.C. and following Desmond’s career from the start, you get the sense that all the "he’s such a nice guy" accolades are true. He has a young family. He does outreach in the community. His teammates love him. He wanted to do more with his money than just buy a Lamborghini Centenario. He put all that at risk for a stupid gamble. (And, frankly, the Nats are probably pretty happy he did.)

This isn’t like when basketball players do the same thing. The sports and their salary structures are far too different. When a baller does it, he’s either unproven or coming off a bad year and signs for a little money in a good situation, relying on his talent and teammates (unlike in baseball, basketball players can hide on an off-night) to get the big contract. Baseball doesn’t work like that. It’s you and the pitcher, or in Desmond’s case, you, the pitcher and the evidently not-so-simple process of throwing the ball to first base.  

7. Desmond was a proven talent, if he didn’t like the $107 million, so be it. Maybe he’ll have the 2016 season he hoped to have in 2015 and get back on track. I hope he does. But the move to left field and the two years of struggles make that a bad gamble, something Ian Desmond knows about all too well.