SAN DIEGO — Gerrit Cole was a fan of the New York Yankees as a kid. The Yankees have also long been admirers of Cole, drafting him in the first round in 2008 when Cole was then a high school senior. Cole spurned the Yankees; he opted to attend UCLA instead, and he was selected No. 1 overall by the Pittsburgh Pirates in the 2011 draft. But Cole and the Yankees were finally brought together by a nine-year, $324 million contract reached on Tuesday night.

The Yankees were expected to be a playoff team with or without Cole — they’ve missed the playoffs only four times this century. But New York hasn’t made it to the World Series since winning it all in 2009, and Yankee GM Brian Cashman wanted Cole, whom he called his “white whale,” to help deliver a World Series title and end a decadelong title drought. After the signing, the Yankees became the Vegas co-favorites to win the World Series.

The good news for the Yankees is that signing elite free-agent pitchers has often helped clubs to World Series titles while the player was with the team — particularly for pitchers yet to play their age-30 seasons. Of the 14 pitchers in addition to Cole who entered free agency coming off of seasons of 5.0 WAR or greater, and were younger than 30 in the previous season, seven went on to be part of World Series-winning teams with their new clubs.

Cole is among the best under-30 free agent aces in history Top pitchers under 30 entering free agency by wins above replacement in their previous season, since 1976 Previous season Pitcher war year age Old Team New Team Won title w/ new team Greg Maddux 9.36 1992 26 CHC ATL ✓ John Smoltz 7.73 1996 29 ATL ATL CC Sabathia 7.16 2008 27 MIL NYY ✓ Gerrit Cole 6.79 2019 28 HOU NYY ??? Alex Fernandez 6.40 1996 26 CHW FLA ✓ Mark Langston 6.37 1989 28 MON CAL David Price 6.11 2015 29 TOR BOS ✓ Goose Gossage 6.11 1977 25 PIT NYY ✓ Carl Pavano 5.76 2004 28 FLA NYY Al Leiter 5.69 1995 29 TOR FLA ✓ Max Scherzer 5.67 2014 29 DET WSN ✓ Doug Drabek 5.39 1992 29 PIT HOU Darryl Kile 5.32 1997 28 HOU COL Mike Hampton 5.30 2000 27 NYM COL John Smiley 5.07 1992 27 MIN CIN “Previous season age” is actual age as of June 30 of that season. Source: Baseball-Reference.com

This isn’t the first time the Yankees have signed an elite, young free-agent pitcher — and the last time, it paid dividends. Eleven years ago to the day Tuesday, the Yankees signed CC Sabathia to a $161 million contract, then a record for a pitcher. The following season, Sabathia helped the Yankees to their most-recent World Series title. Sabathia was named the MVP of the ALCS in 2009 and finished fourth in Cy Young voting.

Among this group of young free agent aces, Cole is elite. Armed with command of a 100 mph fastball and an assortment of diving breaking balls, Cole is coming off the fourth-best season (6.8 WAR) entering free agency among any pitcher under age 30 in that season. He went from an underachieving pitcher in Pittsburgh to an ace in Houston after being acquired in trade prior to the 2018 season — thanks to changes to his pitch mix and a curious increase in spin rate. He compelled big market clubs to get into a bidding war for his services — even the Los Angeles Dodgers, which had taken a few recent winters off from major free-agent signings to get under the luxury tax threshold.

Cole’s deal broke the record for pitchers that had been set a day earlier by Stephen Strasburg, who re-signed with the Washington Nationals. Strasburg and Cole were easily the two best pitchers available on the free agent market this year and were among the best in history: Cole and Strasburg are coming off the 11th- and 12th-best seasons, respectively, in terms of greatest previous season WAR totals entering free agency since the advent of free agency in 1976.

Cole and Strasburg are among the best free agent arms ever Top pitchers entering free agency by wins above replacement in their previous season, since 1976 Previous season Pitcher WAR Year Age Old Team New Team Won Title w/ new team Zack Greinke 9.66 2015 31 LAD ARI Greg Maddux 9.36 1992 26 CHC ATL ✓ Kevin Brown 9.07 1998 33 SDP LAD Roger Clemens 8.24 2005 42 HOU HOU Roger Clemens 7.75 1996 33 BOS TOR John Smoltz 7.73 1996 29 ATL ATL CC Sabathia 7.16 2008 27 MIL NYY ✓ Tom Candiotti 7.05 1991 33 TOR LAD David Cone 6.98 1995 32 NYY NYY ✓ Ryan Dempster 6.83 2008 31 CHC CHC Gerrit Cole 6.79 2019 28 HOU NYY ??? Stephen Strasburg 6.51 2019 30 WSN WSN ??? Alex Fernandez 6.40 1996 26 CHW FLA ✓ Mark Langston 6.37 1989 28 MON CAL Goose Gossage 6.11 1977 25 PIT NYY ✓ David Price 6.11 2015 29 TOR BOS ✓ “Previous season age” is actual age as of June 30 of that season. Source: Baseball-Reference.com

Washington knows full well how important front-line pitching is. The Nationals and Astros met in the World Series with historically good starting rotations. Strasburg, the Nationals’ No. 1 overall pick in 2009, was named the World Series MVP. Teammate Max Scherzer, a previous owner of the record for biggest free agent contract for a pitcher, went a combined 3-0 in the postseason. The Nationals won the World Series in part by relying on their excellent starting rotation.

Scherzer’s then-record contract in 2015 was surpassed a year later by David Price’s deal with the Boston Red Sox. Price then had an excellent October in 2018,helping the Red Sox to a title. Ace pitchers have been paying off for the teams that sign them.

The Yankees’ path to the World Series gets a little easier just by virtue of not having to face Cole in the American League playoffs — after all, it was the Astros and Cole who toppled the New York in the ALCS last year. Cole then watched in frustration from the bullpen, unused in Game 7, as Strasburg and the Nationals defeated the Astros in the Fall Classic. Afterward, while sporting a Boras Corporation ballcap, he said he was no longer an “employee” of the Astros. He’s now an employee of the Yankees, who have 324 million reasons to give him as much work as possible — and plenty of World Series innings, they hope.