When the Yankees signed Gerrit Cole to a record nine-year, $324 million contract before the 2020 season, a giddy Hal Steinbrenner said they would have to win “some world championships” to make the massive investment, the franchise’s largest at the time, to validate.
To be clear, Steinbrenner added “plural” for emphasis.
Five seasons later, the Yankees are 0-for-4 in that pursuit, and fittingly, it was Cole who took responsibility for keeping them alive in October when he took the mound Wednesday night for the do-or-die Game 5 in the Stadium.
This was as close as Steinbrenner has ever come to a title since the Yankees’ last successful trip to the World Series in 2009. And in reality, even with Cole ready to save their season, they were still dealing with quite a great opportunities. The Yankees were the 24th team to fall behind 3-0 in the Fall Classic, becoming only the fourth to avoid a sweep after Tuesday night’s 11-4 loss to the Dodgers in Game 4.
However, neither of these teams made it to Game 6, where Cole comes into the picture. As the Yankees played for their survival in the World Series, Cole’s pinstripe legacy was on the line, earning Steinbrenner the first of his many titles. wouldn’t happen if the reigning Cy Young winner didn’t put in a money-making performance in Game 5. The Yankees expected nothing less.
“I wouldn’t trust anyone else,” Carlos Rodon said Wednesday afternoon. ‘He’s Gerrit Cole. His resume speaks for itself: a future Hall of Famer. It will be a pleasure to watch. I’m excited to see him work.”
Cole has a lot of experience. Wednesday was his 22nd postseason start, third in the Majors since his debut in 2013, behind only Clayton Kershaw (30) and Justin Verlander (25), and he is 11-6 with a 2.91 ERA on that play -off trajectory. The only other time Cole pitched in a World Series was 2019, and with it tied at two games apiece, he won Game 5 with a seven-inning gem (3 H, 1 R, 7 Ks) before the Astros ultimately fell to the Nationals. . Cole signed with the Yankees two months later.
Now Cole has more than a ring on the line in year five of his contract. He can opt out once the World Series is over — a trademark of his agent Scott Boras — but the Yankees then have the option to retain him by activating a 10th year worth $36 million at the end of his current deal.
From the Yankees’ standpoint, they would be paying a 34-year-old Cole due to spring elbow issues that cost him the first 2 1/2 months, $180 million over the next five seasons. On the open market, Cole would clearly be at the top of the class this winter, alongside Corbin Burnes (age 30) and Blake Snell (32) – two other Boras clients.
It seems like a no-brainer for the Yankees to keep Cole after what he has meant for the franchise. Before the elbow failure — numerous diagnostic tests showed nothing more serious than nerve inflammation and swelling — Cole had been the sport’s most durable pitcher, leading the Majors with 664 innings pitched in pinstripes in his first four seasons. As the years and miles pile up, it’s only natural to worry about wear and tear, and the average velocity of his four-seam fastball dropped during his 17 starts to 95.9, down from 96.7 the year before.
Whether the velo drop is a byproduct of his gradual build-up after elbow rehab, or whether age is slowly creeping up on him, is difficult to say. Cole can still hit 99 mph when he needs to, and his final fastball – 88th pitch – of his Game 1 start, at the end of six innings, was clocked at 97.9 mph.
Cole had allowed just four hits and one run to that point, striking out four without a walk, but was still removed after a somewhat controversial decision. Aaron Boone later explained: “Cole was done. You just have to take my word for it.” It’s curious that Cole hasn’t reached 90 pitches in any of his first four playoff starts — he reached 89 in 4 1/3 innings vs. Cleveland in the ALCS — but Boone couldn’t afford to be so conservative in handling his ace in Wednesday’s crucial Game 5.
With a short bullpen, the Yankees needed serious length from Cole, whose October highlight was going seven innings (4 hits, 1 run) in the ALDS Game 4 clincher against the Royals on October 10. Cole advanced past the sixth inning only twice, both in September. He pitched nine innings in a two-hit, seven-strikeout performance against the A’s, his penultimate start, in a game the Yankees won 4-2 in the 10th. As of October, Cole is 1-0 with a 2.82 ERA, and maintaining his normal rest period — save for the nine-day break before the World Series opener — has kept him strong through the postseason load.
“I feel like I’m in good shape right now,” Cole said. “I have a spare while I’m pitching. So if I need to dip into the tank, I can go get it, and then I can go get it again. It’s not a one-time thing.”
Cole had to empty the tank on Wednesday. Without tomorrow, there are no saving bullets now. And this is what all of Steinbrenner’s money was for.

David Lennon is an award-winning columnist, a Baseball Hall of Fame voter and has covered six no-hitters, including two perfect games.