Advising someone to take the biggest contract they can get I understand. Costing a guy $100 mil I don't. Put yourself in Desmond's shoes and I doubt you're so cavalier.
I've been part of a Union before long ago...you're spinning a fairy tale.
Did anyone think, coming of his 2013 season, that Desmond would only get 107 million dollars? There's no freaking way. He was THE BEST shortstop in baseball. He was hitting for power, hitting for average, stealing bases, and playing decent defense with good range. He was, legit, looking at Tulo money. 107 million over 7 years is chump change for his numbers. Hanley Ramirez, Alex Rodriguez, Jimmy Rollins, Barry Larkin, Derek Jeter, Nomar Garcipara and Ian Desmond are the only shortstops to be in the 20/20 club in the last 20 years.
All things concerned, Desmond was "due" 20+ million a year at the time he was offered that extension. Even if you use his contract numbers from his last two seasons in DC, that still equals out to 18 million per year over five years to buy out his free agency years.
I have no idea how to be in Desmond's shoes, because I would never worry about money again if I had gotten the 3.8 million he got in 2013, let along the 17 million he got the next two seasons. All of that absurd amount of money to me. I'm betting that Desmond didn't exactly know what to do either, as he was drafted in high school and had been playing in the minors for peanuts for a while. So you rely on your agent as well as veterans in the PA. And when they say you're leaving 30-50 million on the table and that taking a deal like that will affect everyone else who is looking to make some money, probably going to listen to them.