The five richest contract extensions ever given by the Yankees

For a time, until the late 2010s, the Yankees didn’t usually hand too many contract extensions per se. It was just one of The Boss’ things. George Steinbrenner was a big spender in free agency, sure, but extensions weren’t really frequent.

He wasn’t opposed to re-signing hitters who entered the market after stints with the Yankees, though, which is what happened when Alex Rodriguez exercised his opt-out clause after the 2007 season. He was signed to a mammoth 10-year, $275 million pact that wasn’t technically an extension. But Steinbrenner did hand out a few notable deals to his players before they entered free agency, and after he ceded control of the team and passed, his sons did the same. Here are the priciest extensions handed by the Yankees:

1. Derek Jeter (10 years, $189 million) - 2/9/2001

Derek Jeter was a fresh face of the red-hot Yankees that won four championships from 1996 to 2000. Rookie of the Year, World Series MVP, hitting prowess, popularity among fans and media ... failing to extend him would have been a colossal mistake.

Steinbrenner was never a huge fan of extensions, but Jeter needed to be retained. After the agreement, he delivered “only” one additional World Series in 2009, but the benefits of having him around obviously went well beyond the diamond. Jeter remained in pinstripes for the rest of his career, and no matter what he does as a team president in Miami, he’ll always be linked to the Bronx.

2. CC Sabathia (5 years, $122 million) - 10/31/2011

When the Yankees wooed CC Sabathia to New York, one of the perks of his new contract was that he would have an opt-out after the 2011 season. He was sensational in those first three years, earning ALCS MVP honors en route to the 2009 title as well. Then, after the 2011 season in which he was stellar (3.00 ERA, 2.88 FIP in 237.1 innings), Sabathia seemed prepared to potentially use his opt-out to test free agency and get a bigger contract. However, the Yankees weren’t about to let that happen.

Sabathia, then 31, signed a five-year, $122 million extension that basically tacked on another year, 2016, to his commitment with the Yankees (as well as a vesting option for 2018). He would have made $92 million over the next four campaigns with no extension, so he leveraged his opt-out to add another season. In terms of results on the field, the deal was a mixed bag, as he was great in 2012 before struggling with injuries and ineffectiveness from 2013-15. Thankfully, CC remained beloved in the clubhouse and reinvented himself as a crafty veteran with a 115 ERA+ from 2016-17, helping the Yankees return to the ALCS in 2017.

3. Aaron Hicks (7 years, $70 million) - 2/25/2019

The best season of Aaron Hicks’ career has been, by far, 2018. He accumulated 5.0 fWAR that year, hitting .248/.366/.467 with 27 home runs, 90 runs, 79 RBI, 11 stolen bases, and a career-high 129 wRC+. It made the Yankees’ trade for the former top Twins prospect in November 2015 look like a stroke of genius.

The Yankees gave Hicks $70 million in February 2019, but except for the shortened 2020 campaign (when he had a 124 wRC+ in 54 games), he has missed big chunks of playing time because of injuries. The jury, therefore, is still out on this extension, though the outlook is bleak.

4. Brett Gardner (4 years, $52 million) - 2/24/2014

In the spring of 2014, Brett Gardner was only a year away from free agency when the Yankees decided to tie him up with a four-year, $52 million extension that included a $12.5 million option for 2019. The homegrown outfielder was 31 at the time and coming off a fine season: .273/.344/.416 slash line, eight homers, 81 runs, 24 steals, a 109 wRC+, solid defense and stellar baserunning.

Gardner had a commendable 18.6 fWAR as he finished his current deal and ran through his full extension, so it’s fair to say extending him was a smart call. It was so good that even the power came to round out his game: he hit 101 homers over those six years.

5. Hideki Matsui (4 years, $52 million) - 11/15/2005

After an impactful first three seasons with the Yankees from 2003-05 in which he posted 109, 140, and 128 wRC+ marks, respectively, Hideki Matsui signed a four-year, $52 million extension in mid-November. Although he signed in mid-November, Matsui’s was technically an extension because according to the New York Times, the expiring contract said that the Yanks had to release him and allow him to hit the market if they didn’t sign him by November 15th.

The Japanese superstar remained a highly productive hitter in the middle of the Yankees’ lineup during the mid-to-late 2000s, culminating in a championship in 2009. That season, he took over the DH role and hit .274/.367/.509 with 28 homers and a 127 wRC+. He then won World Series MVP honors with an overpowering week against the Phillies.

Such was the power of “Godzilla.”