Brian Cashman’s 5 best free agent signings since the Yankees’ last World Series

Former Yankees pitcher Hiroki Kuroda. (Paul Sancya/AP)

The Yankees have not been to a World Series since 2009, or roughly 72 years in pinstripe time.

Their drought is now approaching the 17-year one from 1979-1995, which preceded sweeping changes and one of the greatest stretches of dominance in the history of American sports. The last championship run, a swan song for that gilded age in the Bronx, was largely the product of smart and aggressive practices by the front office. One trip to the free agent grocery store got them CC Sabathia, A.J. Burnett and Mark Teixeira, integral parts of the 2009 championship team.

Since then, trades have netted the likes of Giancarlo Stanton, Chad Green and Curtis Granderson, but free agency has been more of an adventure. There have been some misses — aside from the Jacoby Ellsbury debacle, remember the Travis Hafner, Stephen Drew and Kevin Youkilis experiments? — but there have also been some moves that left Brian Cashman on the right side of history.

When the lockout is lifted and the flood gates open again, the Yankees’ general manager needs to fill up his cart again. Whether it’s the game-breaking shortstop that fans have pined for all winter — or more realistically, a series of smaller moves that cost the Steinbrenners a pack of chewing gum and some shoelaces — the club needs another win in free agency, something that’s been few and far between since the first Obama administration.

For now, here are Cashman’s five best free agent pickups since the 2009 parade include a very Yankee-esque big splash, a batting champion, a controversial closer and two underrated boosts from Japan. HIROKI KURODA

Beginning this list with Kuroda tells you just how underwhelming Cashman’s post-2009 track record has been. While Kuroda was better than most remember (all three of his Yankee years included an ERA under 3.75 and a Wins Above Replacement total above 3.0), his tenure didn’t leave much of an impact at all.

Kuroda started only two playoff games for the Bombers from 2012 to 2014, which were also his age 37 through 39 seasons. Cashman was able to originally sign the righty to a one-year, $10 million deal and subsequently bring him back on two modest extensions because of his age.

Placing any sort of confidence in a late-30s pitching arm is risky business. If the franchise wants to try that plan again, they have some options, albeit very unappetizing ones. Zack Greinke (38) and Jake Arrieta (35) are still available, but those two would need a miracle to replicate Kuroda’s mojo. If there is someone out there who can give Cashman three straight years of Kuroda-like presence, he’ll likely be much younger and much more expensive than the Japanese veteran was in 2012.


From a pure on-field results standpoint, Chapman has been one of the best relievers of the last five years. Off the field, he is by all accounts a bad person.

Chapman was suspended for 30 games in 2016 for an incident in which he allegedly choked his girlfriend and fired eight shots in his garage while she was in the house. That suspension technically happened while Chapman was still a trade acquisition for the Yankees. When he returned from the suspension during the 2016 season and the Yankees were clearly not postseason-bound, Chapman was shipped to the Cubs.

After that year, the Yankees brought him back on a five-year, $86 million free agent deal and later inked him to a three-year extension worth $48 million. There’s a conversation to be had about the ethics of welcoming Chapman back while knowing what he did. Cashman was apparently fine with it as long as he kept saving games, and Chapman has done that. His 144 saves, 2.72 ERA and 14.3 strikeouts per nine innings all have helped the Yankees win games, but for many, Cashman’s willingness to have Chapman around at all is a stain on his career.


LeMahieu has lived several different lives in his short time with the Yankees.

In 2019, the contact machine hit .327 and drove in 102 runs. In 2020, he was even better, leading the American League in batting average, on-base percentage and OPS, though that will always carry the asterisk of being during the 60-game pandemic season. During those two years, playing under his first free agent contract with the Yankees, he was one of the game’s greatest bargains. In 2021, he fell back to earth hard.

LeMahieu’s numbers from last year show a perfectly average hitter. His .268 average and .349 on-base percentage aren’t catastrophic, but when paired with the complete disappearance of his power, they become cause for concern.

LeMahieu has plenty of time to play up to the expectations of his six-year, $90 million contract, which he signed right before sharply declining. It’s hard to imagine a guy who’s posted a .300 batting average in five different seasons being as lost as he was last summer, but LeMahieu is still a feather in Cashman’s cap. The 2019 and 2020 playoff appearances don’t happen without him, and should the Yankees return to glory, it’d likely be because of a return to form for the three-time All-Star, not in spite of him.


Other than Sabathia, Tanaka was the Yankees’ best pitcher from 2009-2020. His seven years in Major League Baseball will always leave a little to be desired, but he more than delivered on his $155 million agreement.

A 3.74 ERA, 1.13 WHIP, 114 ERA+ and 18.9 WAR across seven years is objectively good. Argue about it with somebody else.


The lone unquestioned win of Cashman’s recent free agent hauls now also has a major demerit following Cole’s implosion in last year’s Wild Card Game.

Still, there are maybe three or four pitchers in existence who can reasonably claim to be better than Cole since he joined the Yankees. He’s the leader in strikeout rate, WHIP and WAR among qualified AL pitchers during that span, and the beauty of the situation is that he’s got seven more years on his contract to continue dominating.

The best way for Cole to erase the memories from last October at Fenway is to come out firing in 2022. Given his natural abilities, competitive nature, and status as an unassailable regular-season ace, there’s good reason to believe he’ll do just that.[More Yankees] The Yankees’ top 3 priorities when the MLB lockout ends, according to scouts »

If he’s supported in the rotation by another Cashman gem, the Yankees might just find themselves on the brink of ending this drought.