On December 18, 2008, Sabathia signed a seven year $161 million contract. With added extensions he had 11 years of contracts with the Yankees receiving $219 million.
It all started so well for both Sabathia and the Yankees. In his first four seasons he won 74 games. In 2009, he led the Yankees with a 19-8 record. With his leadership, the Yankees won the World Series.
The next three seasons Sabathia continued his dominance However each year his wind dropped from the prior year. He won 21, 19, 15, and 14 games.
Starting in that fourth season, production started to drop in all areas. After 8 years, he had four good seasons and four very poor ones.
He did have a comeback year. In 2017 he had a 14-5 record with 3.69 ERA. However, this would be his last good season for the Yankees.
His final two seasons were, at best, mediocre. 9-7 and 5-8 and were hardly performances justifying the huge money the Yankees were paying. In the end CC Sabathia pitched 11 seasons for the Yankees. He was great for three years and good for two. The other six seasons he won 32 games and lost 41.
How does one measure the success of a contract? The Yankees had some great years with CC Sabathia as their ace starter. The problem is they paid him eleven seasons and a very high level but only received 3 great seasons.