From flipping closers to Carlapalooza: Brian Cashman's greatest hits -- and misses -- in 20 years as Yankees GM

Howard Earl Simmons/NY Daily News Archive via Getty Images

In two decades as GM of the New York Yankees -- 40 percent of his life -- Brian Cashman has accomplished a lot. He has been a part of five championship teams. He has never allowed his franchise to finish below .500. He has survived in a job that once was just a temporary position.

But now he is earning something that has mostly evaded him: respect.

Respect as one of the great GMs in the game, and one, along with Theo Epstein and Billy Beane, who might have a pathway to Cooperstown. If Cashman, 50, can build a new dynasty, it's hard to imagine he won’t end up there one day. By quickly rebuilding with a farm system featuring Aaron Judge, Gary Sanchez and Luis Severino, among others, and now reloading (Giancarlo Stanton), he has turned the Yankees around quicker than a driver can cut you off on the Major Deegan.

Cashman has always had the respect of his peers, from how he dealt with George Steinbrenner to how he routinely made good decisions to better his franchise. He is well-liked.

But outside of the industry, with the media and fans, there has always been a “but” his last name could summarize: Cash Man. In other words, yeah, sure, Cashman has had success, but he's also had boatloads of money.

As he marks his 20th anniversary on the job on Saturday, money has certainly helped. He needed a nearly half-billion dollar class of 2014 (Masahiro Tanaka, Jacoby Ellsbury, Brian McCann and Carlos Beltran) just to keep the Yankees above .500 that year. But when you look at Cashman’s tenure, there are more hits than misses. We narrowed it down to his four best -- and four worst -- moves as GM.

The Top 4

1. The Aroldis Chapman deals: In the Chapman trades, Cashman showed his inner-Boss, doing whatever it takes to win. Before the 2016 season, with Chapman being investigated in connection with domestic violence allegations, Cashman pounced, sifting through the Cincinnati Reds' discount bin after their deal with the Dodgers fell through. He traded four middling prospects (Rookie Davis, Eric Jagielo, Caleb Cotham and Tony Renda) for Chapman, knowing in the back of his mind he might later deal Chapman at greater value.

Half a year later, Cashman flipped Chapman to the Chicago Cubs in a trade that brought back potential future star Gleyber Torres. Then he brought out his wallet and re-signed Chapman for five years and $86 million. You might not like the method, but the results are undeniable.

2. The Bobby Abreu trade: By 2006, the Yankees had already figured out their first-round pick in 2005, C.J. Henry, wasn’t who they thought he'd be, so Cashman quickly cut bait. In return for Abreu and pitcher Cory Lidle, Cashman included Henry, catcher Jesus Sanchez, and pitchers Matt Smith and Carlos Monasterios in a deal with the Phillies. Abreu would be a Yankees success story for three seasons.

3. The Didi Gregorius trade: Cashman has shown a remarkable ability to replace legends. While there might never be another Mariano Rivera in terms of impact and longevity, the Yankees’ closer role really hasn’t missed a beat since Rivera retired. The same can be said at shortstop, as Cashman’s deal to bring in Gregorius to replace Derek Jeter has been sensational.

Gregorius was acquired as part of three-team deal prior to the 2015 season. The Yankees gave up pitcher Shane Greene, who improved in 2017 after two subpar campaigns in Detroit. Gregorius, still in his late 20s, looks as if he could be an All-Star any year now.

4. Stealing Nick Swisher from the White Sox before the 2009 season. Swisher had been terrible with Chicago, but Cashman got a big assist from his sabermatricians when he was brought a study showing Swisher had hit into bad luck.

Cashman gave up a three-player package (Wilson Betemit, Jeff Marquez and Jhonny Nunez), for Swisher, who became a fan favorite and an important member of the 2009 World Series championship team.

The Bottom 4

1. Signing Jacoby Ellsbury: This contract seems destined to go down as the worst in Yankees free-agent history. Ellsbury has given the Yankees little during the first four seasons of his seven-year, $153 million contract. Now, he won’t even start unless there are injuries, trades or severe underperformance. He very well might be the team’s sixth outfielder in 2018 behind Aaron Judge, Giancarlo Stanton, Brett Gardner, Aaron Hicks and Clint Frazier.

2. Signing Kei Igawa: Cashman swung and missed on this one. He signed the Japanese pitcher to a five-year, $20 million deal and received a 2-4 record with a 6.66 ERA in 71 2/3 major league innings.

3. Signing Carl Pavano: Pavano -- snagged by the Yankees after his famed "Carlapalooza" free-agent tour -- was injured again and again, which Cashman defended. At the end of the day, this was more wasted money, as Pavano’s four-year deal for slightly less than $40 million led to a 9-8 record with a 5.00 ERA, those multiple injuries and a whole lot of ridicule.

4. The Jeff Weaver trade: Weaver was acquired in 2002 via a three-team trade with the Tigers and A's, with lefty Ted Lilly the main player leaving the Yankees. Weaver did OK when he came over in July, going 5-3 with a 4.04 ERA. But he struggled mightily his second season, finishing 7-9 with a 5.99 ERA. Most memorably, he gave up the game-winning home run in Game 4 of the 2003 World Series when Joe Torre turned to Weaver instead of Rivera in a tie game. Lilly went on to make two All-Star teams in his career; the Yankees likely would've been better off just keeping him.