Jose Quintana the latest pitcher to opt for early security

Chris Sale leads the White Sox rotation. He signed a five-year, $32.5 million extension last March, and said the process and result overwhelmed him:

"The last couple of weeks I have been thinking about what it was like growing up, where I came from, just a kid from Lakeland, Fla., not really thinking anything too much, going to a smaller college and getting drafted," he said. "You never think about (a huge contract) until it's here and it came and it still blows my mind."

Jose Quintana slots in nicely behind him. He just signed a five-year, $26.5 million contract on Monday, and he's thrilled beyond words:

He reached down and pinched his right arm a couple of times, looked up again and his smile continued.

"I don't know if it's real," the ecstatic Quintana said.

Next in line? John Danks, whose own experience suggests Sale and Quintana cost themselves quite a bit of money.

The last time the White Sox had two starters who were extension candidates at similar points in their careers, only one took the front office up on the offer. Back in 2009, Gavin Floyd agreed to a four-year, $15.5 million extension with a $9.5 million club option to buy out his first year of free agency. Danks declined, waiting until his last year under White Sox control to sign a five-year, $65 million extension.

It's hard to say anybody truly loses when they make $25 million, but looking at the way their careers played out to date, Floyd might have been far better off going year to year.

First, there's the matter of what Danks earned over the span of the original extension that Floyd accepted.

Through his first five years in a White Sox uniform, Danks only outearned Floyd by a couple million despite putting himself at risk. That seems fair enough, because Danks provided a touch more value than Floyd over that same stretch:

But the earnings difference transforms from a gap into a chasm when it approaches the pitchers' original free agency year (2013).

Had Floyd hit hit free agency at the end of his six years of service time, his value wouldn't have been at an all-time high. His workload dipped to 168 innings over 29 starts, his walk rate and HBP totals spiked, and he had a couple different arm problems during the year. But hey, Danks also had a down year before signing his megadeal, and Floyd put together a better finish in his. Proven pitchers tend to get paid.

Instead, the White Sox exercised that $9.5 million option, and an elbow injury ended his 2013 season after five starts. He underwent Tommy John surgery, and now he's trying to get back on track with the Atlanta Braves on a one-year, $4 million contract. (Given the Braves' problems with UCL replacements as of late, a next sizable contract isn't a given.)

Hindsight says the Sox could have spent that $9.5 million elsewhere, but it nevertheless proved the value of buying out a free agent year that early.

Had the Sox signed Floyd to a sizable extension after 2011 of the same career, they would've been on the hook for much more than the $9.5 million. Likewise, had Danks suffered his shoulder injury while on the Floyd extension, they Sox wouldn't have exercised the option in the first place. As it played out, Danks needed capsule surgery just as they started making payments on the $65 million deal, which makes $9.5 million looks like a mere deductible by comparison.

Now, the guaranteed money looks a lot different:

It's going to take a considerable rebound for Floyd to make any dent in that difference ... and yet it's still hard to say Floyd chose poorly. If it were easy, then you probably wouldn't see guys like Sale and Quintana sign their extensions so happily.

Even though Floyd made far less than he could have in an alternate universe, it's possible he'd sign the same contract if he had to do it all over again. The White Sox gave Danks his first chance, but Floyd was on his second. His Phillies career gave him an idea of how difficult it was to stick. Throw in wedding plans (Danks didn't get married until this past winter), and financial security had its pull.

And that's even before factoring in the Butterfly Effect. Perhaps if Floyd never signs the extension, perhaps he hits his first medical crisis far earlier in his career. We're comparing him to Danks, who represents just about the best-case scenario for going year to year.

But then there are guys like Daniel Hudson.

Like Floyd, Hudson put together a breakout performance in his first full season with his second team, going 16-12 with a 3.49 ERA over 222 innings for the Diamondbacks in 2011. In an interview with MLB Trade Rumors, Hudson said he had an opportunity to do an extension, and his agent laid out the pros and cons:

On talking to [agent Andrew Lowenthal] about going year-to-year versus doing a long-term extension:

He laid it all out on the table. He's very good at giving me comparables as far as where I am in my career to where certain guys were at the same point in their careers and what contracts they signed and when they signed them. Before every season he gives me these thick notebooks and explains to me where I'm at in my market level with all the other guys. Obviously going year-to-year is a little bit more risky, but you can make a little bit more money in the long run. Or you can go for the security, if the team is willing to offer you an extension before you hit arbitration. He's very good and very open at giving me his opinion, but at the same time he wasn't for or against either one too strongly. So if the Diamondbacks offered me a contract last year and he didn't think it was a good deal but I wanted the security, he would not pressure me to not sign it.

Did the Diamondbacks throw anything out there before last season?

We talked. We had short conversations, but I don't really want to get into the number aspect of it.

Since that excellent 2011 season, Hudson has battled elbow problems that required not one, but two Tommy John surgeries. In fact, he's doing a lot of consulting for the recent flood of repeat UCL victims. Throw in the other talented young pitchers to receive crushing news this season -- Cory Luebke, Kris Medlen, Jarrod Parker, Brandon Beachy, Patrick Corbin, etc. -- and maybe it would all be enough to even make a guy like Danks sign an early extension nowadays.

When it comes to contract extensions for talented young pitchers, the risk imbalance seems almost unfair for the player. The Sox have never liked five-year deals, but Hahn said these last two have been no-brainers:

"Any club, regardless of their resources, wants to make sure they're allocating them as effectively as possible," Hahn said. "There's risk any time you do a multiyear deal with any player, and the risk is a little bit heightened any time you do it with a pitcher.

"Given where we're at and where we plan on going, we know when we have an opportunity to lock up and extend control over key pieces it's a risk that makes sense. I don't think that's unique to our market. I think any club would want to get a pitcher like Chris Sale or Jose Quintana on terms similar to these."

Then again, for the layman, it seems like an equally easy call to lock in one big contract when your future can slide into a ditch with one pitch. Danks' career may show the immense financial empowerment to be gained by waiting it out, but when you see the (justifiable) excitement from Sale and Quintana in signing club-favorable deals, the road Danks chose could be the one far, far less taken for years to come.

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