When a musician uses another’s work within his own song, it’s called sampling. When a musician flips his own work, it’s called a remix. Billy Beane is doing a little of both by extending Trevor Cahill.  

Throughout the early 1990s, Cleveland general manager John Hart locked up as many young players as he could, including Jim Thome and Manny Ramirez. Beane and his younger disciples have since made pre-arbitration deals sexy, but locking up talented youth isn’t just for the progressive these days, as even the old fogies have gotten in on the act. Whereas Hart mostly focused on positional players (although he did extend Charles Nagy), Beane is quite accomplished in the fine art of starting pitcher extensions. Talented starting pitcher trios and contract extensions have come in cycles for Beane since he became Oakland’s general manager.

The Big Three of Tim Hudson, Mark Mulder, and Barry Zito ruled the American League West a decade ago: Hudson’s sinker, Mulder’s devastating three-pitch combination, and Zito’s curveball and changeup were the stuff of legend. Beane managed to ink each of them to an extension within a two-year span. Hudson (four years, $9.1 million) came first in August 2000, Mulder followed 13 months later (four years, $14.2 million), and Zito got his (four years, $9.3 million) in May 2002.

Hudson would go on to toss 902 innings for the A’s beginning the season after signing the extension, posting a 3.12 ERA in those innings and averaging 32 starts per campaign. Mulder would start only 89 more games for the A’s following his payday, boasting a 3.72 ERA. More importantly, perhaps, Mulder averaged 207 innings per season. (He would go on to throw a total of 311 innings after being traded to the Cardinals and is now retired from baseball.)

Zito would remain in Oakland the longest out of the trio, sticking with the A’s through the 2006 season. Over the life of his extension, Zito would average 34 starts per season, totaling 894 innings pitched with a 3.86 ERA. During that 2006 season, the A’s complemented Zito with Dan Haren, Rich Harden, and Joe Blanton, who would later form their own Big Three.  This trio was more right-handed (in fact, entirely right-handed) and sported a combination of jaw-dropping stuff (Harden), deep arsenals (Haren), and gooey midsections (Blanton).  With a new assortment of would-be aces on his hands, Beane again sprang into action, extending Harden (four years, $9 million) and Haren (four years, $12.65 million) within the span of a single season, with Harden signing in April 2005 and Haren following suit in September.

Harden’s deal is difficult to assess, as he gave the A’s roughly 280 innings after signing (including the entirety of the 2005 season). The quality was good (a sub-3.00 ERA), but the quantity was lacking. Haren’s deal was a more unqualified success; although he would pitch only 68 more games for the A’s, he did so well enough (3.59 ERA) to net a large return, which included a doughy southpaw named Brett Anderson.

Anderson and Cahill have fronted the A’s rotation since 2009. The former signed an extension in April 2010 worth $12.5 million over four seasons, and Cahill received his own deal a year later. While a few pundits have described Cahill as the Athletics’ ace—and he did start for them on Opening Day—that ‘s probably an exaggeration of his abilities.

Cahill still has his merits, though, as he made a drastic improvement from 2009 to 2010. His SIERA dropped from 5.08 to 4.16, and his ERA fell from 4.63 to 2.97. Cahill also made only two starts that lasted fewer than five innings. While the A’s may have expended more resources than normal on their relief corps this winter, teams ultimately would rather see their starters go deep into ballgames than call on the bullpen early, so Cahill’s tendency toward longer outings is another point in his favor.

PECOTA certainly seems to believe in Cahill: his weighted-mean projection calls for him to toss 190 innings with a 3.61 ERA, good for 3.5 Wins Above Replacement Player. Another attribute in Cahill’s favor is his health. The only injury history to show up on his player page is a three-week trip to the disabled list early in 2010 for a stress reaction in his left shoulder. At 6’4” and 220 pounds, Cahill certainly looks the part of a reliable workhorse, and in light of the extension, it’s safe to conclude that the A’s—who enjoy the richest information about any of the pitcher’s preexisting ailments , as well as his conditioning and workout habits—expect him to continue to play the part as well.

Beane broke from tradition in awarding Cahill a five-year extension with a guaranteed payout of $30.5 million, as well as club options for the 2016 and 2017 seasons that would pay the pitcher $13 million and $13.5 million, respectively. Club options are always smart additions to deals from the team’s perspective, for obvious reasons. The cost certainty allows teams to project performance and assess whether the player’s production is likely to match his paycheck. If it is, the team can keep him; if it’s not, the team can still leverage that cost certainty to extract value in a trade with a team that does consider the player worthy of the price.

Like most deals conceived in a player’s pre-arbitration years, this one looks fairly team-friendly. Players at this stage of their careers tend to have less leverage and less immediate earning power than those already entrenched in the arbitration process. The combination of the pre-arbitration timing and club options raises another rare option available to the A’s: they could always trade more money to extract further service down the road.

That sounds obvious—after all, every team trades cash for performance—but if in two seasons Cahill has become Tim Hudson Junior and the A’s have a pile of money to throw his way, an obvious tradeoff will come into play. The A’s could eliminate some of their built-in advantages (from this contract) for a reduction on Cahill’s wages (when compared to his market value). The A’s themselves actually managed this very situation with Eric Chavez and have extended Mark Ellis twice, although the second time he was technically on his way to free agency.

In all of Beane’s years at the helm, he has dispensed only one starting pitcher extension that can be considered a poor idea in retrospect: Harden’s, which tanked because of injury. That successful track record does not ensure Cahill’s success—he could still turn into another Bobby Crosby—but it could suggest that Cahill possesses attributes shared by previous extension signees. The results will take time to assess, but it’s hard to argue against Beane given his past extension exploits—and if Oakland’s previous extension trifecta is any indication, Gio Gonzalez’s agent may want to keep his phone charged and close at hand over the next few months.

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What do you make of Cahill's upped strikeout rate? I know it's an extremely small sample size, but he was striking out more people in ST as well and reports have been that his curveball has been much sharper, so I was wondering if it means the predictions of a statistical regression were overblown.
The reports about his curveball are interesting, but I'd take them with a grain of salt at this point. As you note, it's a small sample. Weird things can happen, even if there is a possible explanation built-in.
He did have decent K numbers in the minors though. He may have been just trying to play it safe before he lets it all lose. Or I assume the organization forced this approach.
"Sh*t"? Really? Is this supposed to be edgy? Or are we simply not supposed to take this publication seriously?
I take it you are not familiar with Billy Beane's famous quote in Moneyball that his shit don't work in the playoffs.
It plays off a direct and famous quote of Billy Beane's, cpaddock. So no, they're not trying for 'gangsta cool'.
I really don't think Harden's contract can be labeled as a failure at all. I quote - "he gave the A’s roughly 280 innings after signing (including the entirety of the 2005 season). The quality was good (a sub-3.00 ERA)" I feel like getting 280 innings of sub-3.00 era baseball for $9 million is a deal most teams would jump at, not to mention the additional value of whatever return the A's got in trading him, however minor it was. Calling the contract a failure seems harsh, even if Harden was unreliable and didn't live up to expectations.
The A's got next to nothing in return for trading Harden (with Chad Guadin): Josh Donaldson, Sean Gallagher, Matt Murton and Eric Patterson.

You can play the line out with Murton for Corey Wimberly and Patterson for fabian Williamson, but why bother?

The real problem is Billy Beane keeps signing retread veterans to be his position players. I mean, for how many consecutive seasons has he signed a mediocre token veteran outfielder? It seems like this year he's just handing out money to keep the union happy.

Mark Ellis : $6M Option exercised
Brian Fuetes : 2 years/$10.5M (2011-12), plus 2013 club option
Kevin Kouzmanoff : 1 year/$4.75M (2011)
Hideki Matsui : 1 year/$4.25M (2011)
Conor Jackson : 1 year/$3.2M (2011)
Rich Harden : 1 year/$1.5M (2011)
Ryan Sweeney : 1 year/$1.4M (2011)

It would've been better to just save the money and play the kids, service time be damned. See what Chris Carter, Eric Sogard, and Steve Tolleson could do in a full season.

I think the real "problem" for Beane is the fact he has 30 million to put together a winning ball club. GIven the talent he has with Gio, Cahil and Anderson, Beane feels he has a better chance of winning with re-tread position plaer veterans opposed to unproven minor leaguers.