Kiermaier extension: Behind the thought process that goes into long-term deals

PORT CHARLOTTE — This should be easy, right?

Agreeing to a contract extension that pays you tens and tens of millions of dollars to stay with your team and keep playing the game you love would seem like a pretty automatic decision.

But it's not always so simple.

Centerfielder Kevin Kiermaier is the latest Ray to sign on, agreeing to a six-year, $53.5 million contract, with a seventh-year option that could push the total value to $64 million, for reasons he happily will share this morning at a Charlotte Sports Park news conference.

These deals require major commitment. The player and team to invest in each other. And to make significant tradeoffs.

Evan Longoria, who has signed two long-term deals with the Rays, said there were a number of factors in deciding to say yes, including precedent.

"The first one I was really anxious, and I'm sure (Kiermaier) was as well, and you just wonder like, 'Is this the right decision? I have all this time ahead of me. I don't know what I'm doing,' " Longoria said.

"What it comes down to is trusting yourself and your ability first but also your agent and the homework that they've done in knowing that you're going to be fairly compensated. … You don't want to sign a bad contract because you have to think about other players and how you are not only setting yourself up but for the future of the game."

Longoria's first deal, finalized a week into his 2008 rookie season, guaranteed him $17.5 million over six years and up to $44 million over nine. It was criticized, branded with the code words "team-friendly" and lumped onto some "worst contract" lists. That's because some agents and/or union officials felt he set the bar too low for future players.

"It was kind of frowned upon, but for me, kind of like it was for (Kiermaier), it's your first fortune," Longoria said. "You're looking at turning down all this money, and there's a lot of unknowns when you haven't played this game at the highest level for very long. So for me, it was like, I can have this security for myself and my family and just play and relax.

"The second contract (a six-year, $100 million deal he is starting this season) was more personal, like, let's weigh all the options, so a little more went into it."

There can be a lot.

The player gets the financial security and accompanying peace of mind while giving up the potential for greater earnings by going year-to-year and getting to free agency sooner. The Rays get cost certainty and additional years of control that could provide a considerable below-market bargain, but they take on the risk of paying through injury or poor play.

Though the Rays don't include no-trade clauses, the deals can afford a player a few extra years in town. But those reasonable salaries and extra years of control also can make him more attractive to other teams, with Matt Moore the latest such example in last year's trade to the Giants.

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All of which allowed starter Jake Odorizzi to feel good about turning down a deal two offseasons ago that would have guaranteed him close to $30 million over six years and could have exceeded $50 million over eight.

"There's pros and cons, and you're committed to this for whatever it is, six, seven, eight years," Odorizzi said. "Sometimes it boils down to, and I hate to say it, but the dollar amount. We all know the money in this game and the value of players and what your value is. And sometimes it just doesn't match up. That's just the circumstances.

"It's a tough decision, really. It's tough to say no to that large amount of money that a lot of people will never see. It's something that if you say no to, you can't think about it. We had talks and we didn't agree. I completely forgot about it because you can't think about the what-ifs of it from outing to outing, like if I'm not doing well, like, 'Oh, man, what if I would have taken the deal and eased my mind, could I be pitching better now? Is this weighing on me?' But for me it was easy."

So maybe it is easy, after all.

Marc Topkin can be reached at mtopkin@tampabay.com. Follow @TBTimes_Rays.