The New York Yankees had just missed the playoffs for the first time since 1993 (third place in the AL East, a fine 89-73 record that got them exactly nowhere), and Brian Cashman decided the fix wasn't subtle roster tinkering. It was buying the best pitcher on the market and building everything else around him.
On December 10, 2008, the Yankees agreed to a 7-year, $161 million contract with CC Sabathia -- the biggest deal ever given to a pitcher. Eight days later he was standing at the old Yankee Stadium in pinstripes, next to A.J. Burnett, telling reporters he wanted to be called "CC," not "C.C." Small thing. Set the tone anyway.
Cashman Gets on a Plane
Here's the part I love: this deal almost didn't happen the boring way, with faxed term sheets and lawyers on a conference call. It happened because Cashman got on a commercial flight.
The Winter Meetings were in Las Vegas that week, and by Tuesday night, December 9, talks with Sabathia's camp had gone quiet enough that it didn't look promising. Then Sabathia's side called and invited Cashman out to the Bay Area to meet the family in person. Cashman didn't wait for a private jet -- he got on a plane to Oakland that same night. (Ownership had already given him the green light to spend, which, given what came next, was doing a lot of heavy lifting in that sentence.)
By Wednesday morning, they had a deal. The Yankees' original offer had been six years and $140 million. Sabathia's side wanted more security, so the Yankees tacked on a seventh year and pushed the total to $161 million -- $23 million a season, obliterating every previous record for a pitcher's contract. There was also an opt-out after year three, in case Sabathia hated New York and wanted an exit ramp. (He never used it. Draw your own conclusions.)
He'd earned the upper hand at the table. Sabathia went a combined 17-10 with a 2.70 ERA between Cleveland and Milwaukee in 2008, and after the Brewers traded for him at the deadline, he was absurd -- 11-2, 1.65 ERA in 17 starts, working on short rest down the stretch to drag a franchise that hadn't sniffed October since 1982 into a wild card spot. That's not just a good year. That's a guy who single-handedly changes what a team believes it can be.
| Contract | 7 years, $161 million |
| Average Annual Value | $23 million |
| Agreement Reached | December 10, 2008 |
| Introduced at Press Conference | December 18, 2008 |
| Opt-Out | After 2011 season (year 3) |
| 2008 Combined Record (CLE/MIL) | 17-10, 2.70 ERA |
| 2008 Record with Milwaukee | 11-2, 1.65 ERA in 17 starts |
| Record at Time | Largest contract ever for a pitcher |
Not the Only Move
Sabathia wasn't a one-off splurge. He was the opening act of the most expensive two-week stretch in franchise history.
Three days later, on December 13, the Yankees signed A.J. Burnett to a 5-year, $82.5 million deal ($16.5 million a year), bringing back a guy with a career-long history of dominant stuff and inconsistent health. Ten days after that, on December 23, they landed Mark Teixeira away from the Red Sox, Angels, Nationals, and Orioles for 8 years and $180 million -- no opt-out, full no-trade, the switch-hitting first baseman the lineup had been missing since Tino Martinez left town.
Add it up: $161 million plus $82.5 million plus $180 million comes out to roughly $423.5 million in guaranteed money, committed in a single offseason, during the worst global financial crisis in 80 years. (NPR ran a piece basically asking how this was legal. Fair question. The Yankees didn't care.)
This wasn't a normal winter, and it wasn't supposed to be. The Yankees were about to open a new billion-dollar stadium in April 2009, and after watching October come and go without them for the first time in 13 years, ownership decided the response to embarrassment was a checkbook, not a committee meeting. Cashman would later admit he'd told Sabathia directly that the clubhouse needed him -- not just the arm, the presence.
I think it adds an urgency to get back to where this organization is supposed to be. I wouldn't say it's pressure. I would just say that people will play with a sense of urgency in the new stadium, getting back to that. It's definitely exciting.
He also copped to how brutal the process had been on him personally.
It was kind of a stressful deal. I was just trying to make sure I made a good decision, the right decision.
Did It Work?
I mean, come on.
Sabathia went 19-8 with a 3.37 ERA across 230 innings in his very first season in the Bronx (4th in the AL Cy Young voting, if you're counting), then threw eight strong innings in Game 1 of the ALCS against the Angels (Mariano Rivera closed it out in the ninth) and started twice more in the 2009 World Series, which the Yankees won in six over the Phillies. Nine years without a ring, ended in year one of a seven-year contract. You don't draw it up better than that.
Cashman took real heat that winter for spending like a drunk sailor while half the country was underwater on their mortgages. Nobody in the Bronx was complaining eleven months later.
The Long Tail
The other thing worth saying: this wasn't a rental. Sabathia stuck around for eleven seasons, retiring a Yankee in 2019 after 3,000-plus strikeouts (you can read about that milestone here) and a first-ballot trip to Cooperstown wearing an interlocking NY on his plaque. Teixeira and Burnett had shorter, messier runs -- Tex got hurt a lot in his back half, Burnett got flipped to Pittsburgh after 2011 -- but on December 10, 2008, none of that mattered yet. All the Yankees knew was that they'd just handed $161 million to a horse of a pitcher, and they were about to spend $262 million more trying to build a team good enough to deserve him.
They got their money's worth. Ask anyone who was in the Bronx that November.
Cashman Flies to the Bay Area
With talks stalled during the Winter Meetings in Las Vegas, Sabathia's camp invites Brian Cashman to meet the family in person. Cashman leaves that night for Oakland.
Agreement Reached
The Yankees and Sabathia agree to terms on a 7-year, $161 million contract -- the richest deal ever given to a pitcher -- after the Yankees add a seventh year to their original six-year, $140 million offer.
A.J. Burnett Signs
The Yankees add a second frontline arm, signing Burnett to a 5-year, $82.5 million deal.
Sabathia and Burnett Introduced
Both pitchers are introduced at a joint press conference at the original Yankee Stadium.
Mark Teixeira Signs
The Yankees beat out the Red Sox, Angels, Nationals, and Orioles for Teixeira, completing an 8-year, $180 million deal and closing out roughly $423.5 million in offseason spending.
World Series Champions
The rebuilt rotation pays off. The Yankees beat the Phillies in six games, with Sabathia starting Games 1 and 4, for their 27th championship.
Frequently Asked Questions
How much money did CC Sabathia sign for with the Yankees?
CC Sabathia signed a 7-year, $161 million contract with the Yankees, agreed to on December 10, 2008. At $23 million a year, it was the largest contract ever given to a pitcher at the time. The deal included an opt-out clause after the third season, which Sabathia never used.
Was CC Sabathia's signing part of a bigger Yankees spending spree?
Yes. Sabathia's deal was the first of three major Yankees signings in December 2008. Three days later they signed A.J. Burnett (5 years, $82.5 million), and ten days after that they landed Mark Teixeira (8 years, $180 million). Combined, the three deals totaled roughly $423.5 million in guaranteed money in a single offseason.
Why did the Yankees spend so much money that offseason?
The Yankees had just missed the playoffs in 2008 for the first time since 1993, finishing 89-73 in third place in the AL East. With a new, more expensive Yankee Stadium opening in April 2009, ownership backed a spending spree aimed squarely at rebuilding a rotation that had aged out of contention.
Did the Sabathia signing pay off for the Yankees?
Almost immediately. Sabathia went 19-8 with a 3.37 ERA in his first Yankees season (2009), finished fourth in AL Cy Young voting, threw eight strong innings in ALCS Game 1, and started twice in the World Series as the Yankees beat the Phillies in six games for their 27th title -- their first championship since 2000.