25 Smartest Moves of the Past 25 Years: CC Sabathia signed

The New York Yankees are always looking for quality pitching, no matter what (or at least they should). In late 2008, they were fresh off their first season without making the playoffs since 1993. CC Sabathia was the best pitcher available in free agency.

That 2008 Yankees rotation had Mike Mussina as the ace. He and Andy Pettitte pitched over 200 frames and were the only pitchers to surpass 115 frames. Chien-Ming Wang (4.07 ERA in 95 innings) and Joba Chamberlain (2.60 ERA in 100.1 innings) made some successful starts, but there were some ugly performances, too.

Darrell Rasner (!) made 20 starts and had a 5.40 ERA, Sidney Ponson made 15 (5.85 ERA), and Carl Pavano’s comeback consisted of 8 starts (5.77 ERA). Meanwhile, young arms Phil Hughes and Ian Kennedy had high hopes, but they both got clobbered. In eight games, Hughes had a 6.62 ERA and Kennedy had an 8.17 ERA in nine. Yikes.

Needless to say, CC and the Yankees were made for each other. Sabathia had led the Milwaukee Brewers to the postseason with a marvelous second half after coming over from Cleveland in a midseason trade. With the Brew Crew, the southpaw had a 1.65 ERA (2.44 FIP) in 130.2 innings, making multiple starts on short rest down the stretch to clinch Milwaukee’s first playoff berth in 26 years.

Sabathia entered free agency as a 28-year-old left-hander with a Cy Young Award (2007) and three All-Star berths. Of course the man was going to get paid.

Contract details: Signed to 7-year, $161 million contract (with opt-out after Year 3)

Transaction Date: December 11, 2008

NYY stats during first contract (2009-11): 101 G, 705 IP, 3.18 ERA, 138 ERA+, 3.27 FIP, 624 K, 8.0 K/9, 2.6 BB/9, 1.189 WHIP, 17.1 fWAR, two-time All-Star (2010-11)

In the middle of the Winter Meetings in Las Vegas, Yankees’ general manager Brian Cashman received a call from CC Sabathia’s camp. He wanted to meet in California, so Cash took off and met the pitcher there, as well as his representatives.

“We had the opportunity to [meet] in Vegas, but I also wanted to get the opportunity to meet the family if it was possible,” Cashman said, per MLB.com, back then. “I told them I would be more than willing to fly from Vegas to continue our efforts by meeting in California. They welcomed that idea, so I took advantage of it and bolted.”

Cashman sold the lefty into playing in the Bronx and signed Sabathia to a huge seven-year, $161 million deal, with an opt-out after the third season to give him an exit strategy — just in case the West Coast kid didn’t take to New York. Thankfully, it was the beginning of a beautiful relationship.

Those first three seasons after signing the deal were excellent: the Yankees won the 2009 World Series and the hulky lefty had 5.8, 5.5, and 5.8 fWAR finishes in 2009, 2010, and 2011; with 3.37, 3.18, and 3.00 ERAs, respectively. He surpassed 230 innings each year, and in that 2009 run to the championship, he had a sterling 1.98 ERA and .607 OPS against in 5 starts a couple on short rest), earning ALCS MVP honors for his dominance over the Angels.

Given Sabathia’s opt-out, the Yankees knew that they would have to figure out a way to keep a performer like that in pinstripes after his third season ended, especially since the 2011 rotation outside of CC was a little lacking in future potential. He could have easily walked away and found a better deal in free agency than the remaining value of the contract.

So the Yankees negotiated a new deal that tore up the last four seasons of Sabathia’s original contract, gave him an extra year, and also offered a vesting option for 2017. All told, it was a five-year, $122 million extension.

Sabathia had another solid season in 2012 (3.38 ERA in 200 frames), but his performance slipped after that as he battled both personal demons and injury: over a three-year span from 2013 to 2015, his ERA finished were 4.78, 5.28 (in 46 innings), and 4.73. Great pitchers make adjustments, though, and Sabathia — this time pitching mostly on one-year deals — was solid for a three-year stretch from 2016 to 2018, as his ERA was in the 3.00s every year. He called it a career after his one more go-around in 2019 and remains a beloved part of the Yankees community.

Overall, signing Sabathia in that 2008 winter was the right choice and paid off because it helped bring the franchise’s first championship since 2000. The southpaw was also rock-solid for most of the contract. Over the course of those three seasons covered in the original contract (2009-11), Sabathia accumulated 17.1 fWAR, or 5.7 per season. He was exactly the ace the Yankees needed.

The Yankees’ courtship that year, in the end, paid off for both sides: “It was kind of a stressful deal,” Sabathia said of the free-agency process. “I was just trying to make sure I made the right decision. Being here now and coming here and seeing the way people are, I definitely made the right choice.”