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Chris Sale and the timing of a young pitcher's first big deal

Barring a trade, Chris Sale is going to be with the White Sox until 2019. Why would he agree to a deal like that before he reaches arbitration?

Also of note: He's 87 pounds and his arm is going to fly off. Photo credit
Also of note: He's 87 pounds and his arm is going to fly off. Photo credit
Ed Zurga

Last year, there was an annoying addition to the baseball lexicon: "Matt Moore-type contract."

Hey, (team) should sign (pitcher) to a Matt Moore-type contract.

Before that, it was an "Evan Longoria-type contract", but let's focus on the pitchers here. A Matt Moore-type contract is a long-term deal given to a young pitcher with several team options at the end of it. Before Moore made his third start in the majors, the Rays guaranteed him a little over $15 million. In return, the Rays can control him for two years longer than they otherwise would have. Which naturally means it's a good idea for every team to offer, and a good idea for every pitcher to sign.

Except it's not quite so simple. With the news that Chris Sale signed a five-year, $32.5 million deal with two team options, let's look at when it's a good idea for a young pitcher to sign a contract.

Good timing - Matt Moore

Moore, an eighth-round pick, signed for $115,000 in 2007. That might sound like a ton of money to you, but consider that he spent the next four years in the minor leagues, where players are paid with buttons and old National Geographics. The signing bonus and his minor-league salaries might have added up to an average annual salary of $40,000. Not bad for a kid coming out of high school in any other profession, but consider that he passed up a college education to work in an industry that could have spit him back out in his late 20s or 30s without any money or marketable job skills.

So when there's a chance to get a guaranteed $15 million in this situation, with the downside being that you're paid "only" $19 million more to delay free agency by two years, it's not a bad idea to take it. Or, to put it in pop-culture terms, every rookie pitcher who doesn't get a big draft bonus is playing a rigged game of Who Wants To Be A Millionaire when it comes to his future earnings:

Host: Okay, if you get this right, you win the million dollars. If you get it wrong, you leave here with just $25,000. Are you sure you don't want to leave here with the $500,000 total you've already won?

Contestant: I'm sure.

Host: Here goes. In 1834, which inventor was granted a patent on a device known as "The Reaper?"

Contestant: I know this! Cyrus McCormick!

Host: Oh, no, I'm so sorry. The correct answer is "Your labrum is torn."

Contestant: Wait, what?

Host: /pushes button that drops contestant into a tank filled with electric eels

There's a risk for young pitchers to signing a contract like Moore's. That risk is that they will have to settle for moderate wealth instead of extravagant wealth. There are worse fates.

Odd timing - Matt Cain (the second time)

Matt Cain has actually signed three different long-term deals with the Giants -- the first was a four-year, $9 million contract with an option signed after his first full season. Which, while a little light, is kind of like the Moore deal. It was instant security for life, so you can't blame a player for going for it.

Toward the end of that, though, the Giants and Cain agreed to another deal for three years, $27.25 million that bought out a year of free agency. This is why it took until last year for Cain's career earnings over five years to surpass a year's worth of Barry Zito.

Of course, Cain's doing just fine, having made it through the injury gauntlet to earn a nine-figure deal. But that extra year of team control was a big deal. Cain would have been a free agent at 27, and he would have been a free agent a year earlier after this latest deal. He got to that big, monster extension after all, but it's always scary for a pitcher to postpone that kind of opportunity for a year. There's too much that can happen to pitchers, especially for one who a) had first-round money already, and b) signed a $9 million deal earlier in his career.

Bad timing - Clayton Kershaw, Tim Lincecum, David Price

As in, it would have been a little odd for them to do an extension like Sale's, so they didn't sign one. All three were high first-round picks who secured bonuses over $2 million. So if you're going back to the Who Wants To Be A Millionaire analogy, now you have a much more realistic safety net. And once they started pitching at a Cy Young level, there was no reason to sign away a couple of years of team control. All three will make more money in their arbitration years than pitchers like Moore and Sale will over the life of their long-term deals.

Now, Lincecum might have cost himself a nine-figure deal by not agreeing to an extension before the 2011 or 2012 season. Them's the risks. But he'll still have made $64 million after this season, which is almost twice as much as the value of typical pre-arbitration contracts given to pitchers. When you're almost in arbitration, and you're at a Cy Young level, it's best to wait.

The best timing - Everyone else

Jim Margalus over at South Side Sox has a great compilation of the pitchers who signed similar deals to Sale. The list:

  • Madison Bumgarner
  • Jon Niese
  • Derek Holland
  • Jaime Garcia
  • Trevor Cahill
  • Clay Buchholz
  • Ricky Romero
  • Yovani Gallardo

That's almost a perfect sample of pitchers. Gallardo would have been an expensive free agent after this year, but he has to wait until after 2015 and hope nothing happens before then. But Romero is broken, and the odds are iffy that he'll ever see a $30 million contract again. That's the spectrum of risk. Garcia can't shake shoulder issues and Buchholz hasn't reclaimed that 2010 touch yet, but Cahill and Bumgarner would be pretty close to substantial arbitration paydays. Even when the news is bad in these cases, though, it's bad in the have-scores-of-millions-already kind of way.

That's where Chris Sale was, and that's why he signed the deal with the White Sox. It's why he feels good, and it's why the White Sox feel good. It's how there can be a win-win deal that makes everyone happy. I'm not saying every good young pitcher should sign a long-term deal before their third season … but most of them should. Sale had the first-round money that might have made him comfortable, but he's also had arm scares already. Now he can share the risk.

Just ignore that this was an article about the millions other grown men should settle for, written by a writer who will be in a rented apartment until the end of time.

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