New York Yankees Season Preview: The Rich Get Richer–But Not Healthier

Both the Yankees and Dodgers look primed to win it all in 2020. This season will be New York's, though.

Editor's note: Welcome to SI's MLB preview. Click here to view every team's outlook in 2020, including predictions, projections and, yes, a preview of the 2030 preview. Click here to read the Yankees fantasy preview.

Every few years the Yankees decide to flex their financial muscles. In 2009 they signed CC Sabathia, Mark Teixeira and A.J. Burnett en route to a title. Five years later the Bombers brought in Jacoby Ellsbury, Brian McCann and Masahiro Tanaka, with lesser results. Now, they’ve signed righty Gerrit Cole to a nine-year, $324 million deal, the largest ever for a pitcher.

Cole was the one that got away, New York’s first-round pick in ’08 (No. 28) who chose to attend UCLA instead. He would be the No. 1 choice in the draft three years later, developed by the Pirates then unleashed and perfected by the Astros. Last season Cole whiffed 326 batters; since the mound was lowered in 1969, only Randy Johnson and Nolan Ryan have struck out more.

The Yankees have been an ace short the last few Octobers, including in ’19, when no starter pitched into the seventh in nine postseason games. Meanwhile, for Houston, Cole averaged 7 1/3 innings over five playoff starts, going 4–1 with a 1.72 ERA.

New York is certain to be in the title mix, especially now that the Red Sox have unloaded outfielder Mookie Betts, the second-best player in baseball. (The Rays are a threat, but only if everything goes right.) Even with concerns about the rotation behind Cole (Luis Severino, who was an All-Star in ’17 and ’18, will miss ’20 after Tommy John surgery), the Yankees enter the season with the same dominant offense and shutdown bullpen that nearly got them to the World Series. With Houston, the team that stood in the way of the Yankees’ winning the AL pennant in ’17 and ’19, now diminished, in part because of Cole’s departure, the Yankees are better positioned than they have been in years to win title number 28.. — Joe Sheehan

Projected Record: 105-57, 1st in AL East

Aaron Boone’s “Savages in the Box” won 103 games in ’19 despite a wave of injuries.
Now they have Gerrit Cole—and largely the same roster from last season.

Key Question: How many games will Giancarlo Stanton play?

Giancarlo Stanton faces the most pressure of any player because the $325 million man played in just 18 regular season games, five in the postseason—just two of the six in the ALCS—and he's likely to begin 2020 on the injured list. If he wants to change what’s ultimately been a disappointing first two seasons with the Yankees, he has to stay healthy. — Matt Martell

Player Spotlight

Moving Up: Jordan Montgomery, SP

Montgomery missed most of 2018 and ’19 after Tommy John. The lefty, now healthy, provides a credible replacement for the injured James Paxton.

Moving Down: J.A. Happ, SP

Happ’s ERA has risen for three straight years, and he allowed 34 homers in ’19. It’s hard to expect the lefthander, who turns 38 in October, will bounce back.

Watchability Ranking: Please Watch

The Yankees originally seemed like a must-watch on the strength of their roster alone… but 2020’s apparent reprise of 2019’s next-man-up contest is eminently watchable in its own way. (Who’s this year’s Mike Tauchman? See, it’s intriguing!) — Emma Baccellieri

Preview of the 2030 Preview

Jasson Dominguez, OF: Dubbed “The Martian” and compared to Mike Trout when he signed at 16 from the D.R. in ’19, Dominguez has followed Jason Heyward’s career path (minus the elite glove): ups and downs, more good than bad, but the prevailing feeling is disappointment over his unfulfilled potential. One good year before free agency could boost both Dominguez and the Yankees, who are reeling from two sub-.500 seasons after six straight playoff appearances. Manager CC Sabathia’s job is on the line. — Craig Goldstein