Extending Chris Sale: Examining eight comparable cases

While most of the White Sox enjoyed an off day, Chris Sale went to work early on Wednesday, throwing the equivalent of four innings and 65 pitches against an assortment of the organization's minor-league hitters to rave reviews from Don Cooper.

Projecting his schedule from this point, he's on track to make the Opening Day start on April 1. Robin Ventura remains mum on the subject, as he is wont to do, especially with matters regarding inessential titles.

Before it gets to that point, it's possible that he could earn another honor by receiving the Sox's second-ever five-year contract for a pitcher.

Other media outlets have expounded upon Dan Hayes' report on Tuesday of extension talks between Sale's side and the White Sox. We discussed it Wednesday morning, and with the dearth of other news, it gave me time play with MLB Trade Rumors' Extension Tracker (followed by a visit to Cot's Basball Contracts) to get an idea of what the sides might be talking about -- and why they're talking in the first place.

Below is a review of eight recent extensions over the last three years for pitchers with circumstances similar to Sale's. Sale's body of work isn't a perfect match due to his early bullpen work and incredible transition to the rotation, but with one full year of starting under his size-18 belt, his peer group likely levels out well enough to determine some parameters.

Just so we know what we're comparing these cases to, Sale has two years and 61 days of service time, over which he has accrued this record:

Now that we have this established, let's see where it takes us.

Madison Bumgarner: Five years, $35 million

• Service time: 1.127
• Contract: 2013: $0.75M; 14:$3.75M, 15:$6.75M, 16:$9.75M, 17:$11.5M, 18:$12M club option ($1.5M buyout), 19:$12M club option
  

Bumgarner signed this deal on April 17, 2012, and it didn't touch his 2012 salary of $560,000, although that was offset by a $1 million signing bonus. It also insured him against potential Super Two losses, although he didn't end up qualifying. His final pre-arb salary is higher than Sale's, and it goes on to be the most lucrative contract of the bunch based on the arb-year escalation. The Giants ultimately have say over his first three years of free agency, including no buyout for his final year.

Reaction from McCovey Chronicles: "It's easy to get too giddy about this move -- the Giants had Bumgarner around for a long, long time when they started the day, and they still do -- but that doesn't mean this isn't a great deal. Those options at the end, man. So good."

Jon Niese: Five years, $25 million

• Service time: 2.107
• Contract: 2012:$0.7695M, 13:$3M, 14:$5M, 15:$7M, 16:$9M, 17:$10M club option ($0.5M buyout), 18:$11M club option ($0.5M buyout)

Niese began his career by underperforming his FIP. The Mets bet on that upside by locking him up before Opening Day of 2012. The Mets could control over Niese through his first three free agency years, including club options for the last two. (Postscript: In 2012, Niese posted a 3.40 ERA and a 3.80 FIP. So far, the Mets are sitting pretty.)

Reaction from Amazin Avenue: "This one has potential steal written all over it."

Derek Holland: Five years, $28.5 million

• Service time: 2.120
  
• Contract: 2012:$1M, 13:$3.2M, 14:$5.4M, 15:$7.4M, 16:$10M, 17:$11M club option ($1.5M buyout), 18:$11.5M club option ($1M buyout)
  

Holland is a decent comp in terms of service time and momentum, as the Rangers signed him coming off a breakout season (and postseason). Finalizing the extension on March 20, 2012, Texas gave him a significant raise for his final pre-arb season, but the rest of his raises are more typical of this ilk. Like everybody else, it potentially takes care of his first three free agency years, with two club options.

Reaction from Lone Star Ball: "Those are very team-friendly option numbers, and pretty well solidifies my opinion that this is a great signing for Texas."

Trevor Cahill: Five years, $30 million

• Service time: 2.011
  
• Contract: 2011:$0.5M, 12:$3.5M, 13:$5.5M, 14:$7.7M, 15:$12M, 16:$13M club option ($0.3M buyout), 17:$13.5M club option ($0.5M buyout)

While Cahill is nothing like Sale in terms of style, he signed this deal coming off a similarly successful season, and in the same service-time situation. He made the All-Star team and finished ninth in AL Cy Young voting. He signed the deal on April 11, 2011, which overwrote his $440,000 in his final pre-arb year. It's tied for the highest guaranteed salary of the bunch in his first free-agent year, plus two club options afterward.

Jaime Garcia: Four years, $27 million

• Service time: 2.151
  
• Contract: 2012:$3.25M, 13:$5.75M, 14:$7.75M, 15:$9.25M, 16:$11.5M club option ($0.5M buyout), 17:$12M club option ($0.5M buyout)

The Cardinals and Garcia struck a deal during the 2011 All-Star break, so here's a template if the Sox and Sale wait until midseason. Garcia was in the midst of a fine encore, with a 9-3 record and a 2.23 ERA at the time. And we're back to the standard first free-agency year guaranteed, followed by two club options.

Reaction from Viva El Birdos: "The Cardinals were able to negotiate two club option years in 2016 and 2017 when Garcia will be 31 and 32, respectively. If he's performed well during the prior seasons, the club options value him along the lines of a 2-3 win pitcher. The club will get the opportunity to reassess Garcia's value prior to having to make that decision. That's a tremendous opportunity to retain a top performer or cut bait if a player has fallen apart for any reason."

Clay Buchholz: Four years, $29.945 million

• Service time: 2.069
  
• Contract: 2012:$3.5M, 13:$5.5M, 14:$7.7M, 15:$12M, 16:$13M club option ($0.245M buyout), 17:$13.5M club option ($0.5M buyout)

Buchholz's service time comes closest to matching Sale's, as does his potential-realizing performance leading up to the extension. He led the league in adjusted ERA, made the All-Star team and finished sixth in AL Cy Young voting. He certainly took a different route in getting there, thanks to injuries and a little bit of typical Boston turbulence.

This extension became official on the same day as Cahill's. It's not quite the same, because it didn't touch his last pre-arb year, but it's pretty much identical afterward, including the sizable jump from his last pre-arb year to the first year of free agency.

Reaction from Over The Monster: "A perhaps unintended side effect of the contract could be the mental effect on Clay. Considered by some to be something of a head case, having all this taken care of for the next four years--not to mention the aforementioned financial security--could help him to take things easier."

Ricky Romero, Five years, $30.1 million

• Service time: 1.132
• Contract: 11:$0.75M, 12:$5M, 13:$7.5M, 14:$7.5M, 15:$7.5M, 16:$13.1M club option ($0.6M buyout)

Ignore the service time figure -- Romero and the Blue Jays hammered out their deal in August of 2010, so his deal is basically the same as a guy in his last arb year. The structure of his deal is unique because it's frontloaded relative to the pay scale. He received a $1.25 million signing bonus, and he made more in his first arb-eligible year than his peers here. However, he won't get a raise from his last arb year to his first open-market season, although Romero potentially has an exit advantage with just one club option year.

Yovani Gallardo: Five years, $30 million

• Service time: 2.112
  
• Contract: 2010:$0.5M, 11:$3.25M, 12:$5.5M, 13:$7.75M, 14:$11.25M, 15:$13M club option ($0.6M buyout)

Gallardo signed this extension with the Brewers on April 8, 2010, overwriting his final arb-year salary of $450,000. It gave him full no-trade protection through 2012, then 10-team no-trade lists afterward. Here's another deal where it only has once club option after his first free-agency year. Gallardo seemed to get more concessions than the others.

Reaction from Brew Crew Ball: "Gord Ash told reporters it's 'rather unique in how the deal is structured.'"

Takeaways

The Sox could very well sign a second pitcher to a five-year contract, even though John Danks broke that barrier in a thoroughly unsatisfying fashion. Then again, if the Sox and Sale took a little time coming to terms, they could start the clock on his first arb year and limit it to four. A return to the days of four-year caps for pitchers might not apply to this.

Sale's trajectory doesn't seem like it should be weighed heavily or uniquely. Although his outstanding relief work bolsters his career rate stats, he has plenty of company in the starter group. Bumgarner, Holland, Cahill and Buchholz each struck deals after triumphant seasons, and all of them were in the same neighborhood.

It seems like the Sox would be behind the curve if an extension failed to cover Sale's first free-agency year with two club options afterward. Maybe Sale would be more aggressive in negotiations because of economic conditions and a settled CBA, but I wouldn't assume that to be true. At the very least, the environment could allow the Sox to work out one club option to cover the second free agency year, a la Gallardo or Romero.

We don't have a read on Bumgarner's post-extension path yet, but almost every other pitcher has remained on track to outearn their contracts to varying degrees. Even Holland, who disappointed in 2012, is still in good shape. It gets hairier with Romero, who had all sorts of issues with his repertoire in 2012. The frontloading offsets some of those concerns, at least.

The Cardinals are living the most dangerously, as Garcia had shoulder problems throughout the second half of 2012 and opted against surgery. That's the kind of crisis it takes to thwart this kind of deal, and even then, it's not as bad as extending a pitcher late in the game like Danks. And so far, the early returns for Garcia are positive.

Speaking of Danks, if you were to retrofit his year-to-year salaries into this kind of five-year contract, it would come out to five years and $32 million. Given that Danks had considerable momentum (and innings) coming into his arb years, that pretty much represents Sale's earning potential over the next half-decade, independent of pot-sweetening tactics.

Basically, if you're mentally allocating money for a healthy, happy Sale for the near future, set aside $30 million -- something along the lines of $3.5 million, $5.5 million, $7.5 million for his arb years, plus $12 million for his first free-agency year. That leaves wiggle room for a pre-arb raise, a signing bonus, or other Rick Hahn flourishes.

That Danks signed an extension after maxing out a year-to-year path suggests that finances alone won't get in the way of a Sale extension. It would take a dire set of circumstances for such a commitment to be a bad pursuit. If both sides can't come to terms, it'd be because one side is more nervous than it lets on, the other side is exceptionally exuberant, or an uneven combination of the two.