By Jonathan Bernhardt

First things first: $100 million is a whole lot of money.

That's the commitment the Tampa Bay Rays made to Evan Longoria on Monday, extending his contract an additional six years and keeping the star third baseman and face of the franchise in a Rays uniform for the next decade. There are kids in elementary school right now that will get kicked out of prom before Evan Longoria is a free agent again.

Longoria missed much of 2012 with hamstring injuries, which made it easy to forget that when he's healthy he's one of the best third basemen in baseball. The six-year, $100 million extension is very similar to the one the Washington Nationals inked with their own third baseman, Ryan Zimmerman, last winter, and while Zimmerman is very good, Longoria hits better, fields better and is a year younger.

So even within the confines of a contract extension -- where the team that holds the player's rights doesn't have to bid against anyone else, just come to an agreement with the player and his agent -- Longoria signed for less than might reasonably be expected for a player of his talent, age and history. Zimmerman even had a similar lost 2011 campaign before inking his extension, and there was a year of escalating television deals and resulting mega-contracts between then and now. There's a decent argument to be made that by signing this extension with the Rays, Evan Longoria walked away from a free-agent contract worth maybe twice as much.

Which brings us back to the first point: $100 million is a whole lot of money. That most people won't make that in their whole life goes without saying; any given group of one hundred people making that their entire lives is even a bit unlikely, the way wages are trending in this country. Anytime someone is willing to guarantee a person $100 million dollars to do something as morally stain-free as "play baseball for a decade," it's pretty hard to judge him for signing up. Assuming you play your cards right financially (read: under no circumstances whatsoever invest in steakhouses) that's not just lifetime money; that's great-grandkids' lifetime money.

So even if there's a decent chance that Longoria could have gone out and gotten something in the $22 million a year range on the open market come winter 2016, that's all there is: a decent chance. A whole lot of things could go wrong between then and now for the third baseman to have that free-agent paycheck slashed, starting with his hamstrings. Third basemen don't fall apart at the rate that second basemen do, but it's not exactly a low-impact position, especially if a player is prone to leg injuries -- the position is called the hot corner because of the quick, jerky reactions that the guys playing it need to make while standing in the firing line of every right-handed pull hitter in baseball. If that's not agreeable to Longoria's lower legs as he ages, he could find himself on the disabled list or in the DH spot more and more as the years go on, and that means less money come free agency. Or, he could sign the contract for $100 million right now and never have to worry about money again.

It's not the school of thought that another elite third baseman, Alex Rodriguez, subscribed to in his contract dealings -- A-Rod is almost as notorious for getting paid as he is for hitting the baseball -- but Rodriguez is a first-ballot Hall of Famer who's been recognized as a generational talent since his late teens. And even though it worked out for him, gambling financial security on being able to reach free agency in your late prime without any whammies isn't for everyone. Especially not people being offered $100 million, which, I'm not sure if I've mentioned this, is a whole lot of money.

This isn't the first time Longoria has shown a different, more risk-averse approach to contract negotiations than his peers. His last contract, signed in 2008, was also for six years but only ("only") $17.5 million. As Longoria was in his early twenties and looking like a budding perennial MVP candidate, this was hailed as a brilliant signing by Rays GM Andrew Friedman, billed as the "best contract in baseball." Best is relative, of course, and here it refers to the point of view of management; baseball's a team sport, and since fans are all but guaranteed to privilege their teams over the players on them, that's how they assign value. It was certainly the most team-friendly contract in baseball, given the quality of the player and value of the deal. (Note: $17.5 million? Still a lot of money.)

But this most recent deal might qualify for true Best Contract in Baseball status because of what it represents for everyone involved. For the Rays, it locks up a guy who, if he keeps playing like he's playing now over the life of the deal, is going to be a perennial All-Star with a borderline Hall of Fame floor (the Hall hates third basemen, so who really knows what Longoria would have to do to make it in -- it would probably involve a ring and an MVP award or two). For the Rays' fans, it keeps the face of the franchise in town and involved for the next decade, something every other fanbase in the AL East has been treated to at one point or another in recent history but which has been sorely lacking in Tampa.

And for Longoria, well, $100 million is a whole lot of money.

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Bernhardt is a freelance sportswriter who has contributed to Baseball Prospectus, The Classical and ESPN's Sweet Spot blog network, among others. You can follow him on Twitter @jonbernhardt.