Yankees: Remembering Brian Cashman’s Best Trades on His Birthday

Brian Cashman is a trade-making God for the New York Yankees. Happy birthday!

New York Yankees GM Brian Cashman remains one of the best in the business — he hasn’t lost his fastball at all through the age of 53, which he turns on this very Friday.

In order to celebrate the Cash God/Ninja Cash’s day right, we figured we’d dive back in to some of his greatest deals of all time.

Buckle up — there’s a lot of them. He’s good at this.

5. The Bobby Abreu Trade

Bobby Abreu was an All-Star, and then suddenly he was a Yankee.

When Brian Cashman pulled the trigger on the Bobby Abreu trade with Philadelphia in the summer of 2006, the rest of MLB was uniquely positioned to rip off the Yanks and demand the world of them.

After all, who would possibly make concessions to the team that had made the ALCS back-to-back seasons, and sported an overstuffed lineup already?

Somehow, Cashman still managed to own the Phillies in this deal. Legitimately…how?

Abreu went to the Yankees at the ’06 deadline, along with pitcher Cory Lidle, in exchange for reliever Matt Smith, 2005 first-round pick CJ Henry, and low-level minor-leaguers Jesus Sanchez and Carlos Monasterios. The NYY got Abreu for 2.5 years, and although they didn’t win a World Series with him in right, he knocked in over 100 runs in ’07 and ’08, living exactly up to his end of the bargain.

As Jayson Stark wrote at the time, “I know for a fact there were teams that offered better prospects for Lidle alone. I don’t get it.” Just baffling.

4. Wilson Betemit for Nick Swisher

Somehow, the New York Yankees jumpstarted their ’09 World Series hopes with Nick Swisher.

Sometimes (often?), it’s the small deals you never expect to matter that end up dictating the trajectory of an entire season.

On Nov. 13, 2008, Cashman pulled off a classic heist when he imported Nick Swisher, coming off a down year with the White Sox, and surrendered utility man Wilson Betemit, 2004 first-rounder Jeff Marquez, and Jhonny Nunez (who spells his first name incorrectly).

Swish, who hit just .219 with 24 homers in 2008 with a Sox team that did make the postseason, carried the Yankees’ lineup immediately upon his arrival in ’09 (without A-Rod behind him), and finished the year with 29 homers and a .371 OBP, putting an iconic stamp on the staid franchise. If Swish doesn’t team up with AJ Burnett and start pieing people in the face, do the 2009 Yankees reach their eventual highest heights? Truly, we can’t guarantee it.

Without Cashman’s buy-low move, the 2009 season wouldn’t have felt nearly as magical.

2. The David Justice Trade

David Justice arriving in New York sealed the Yankees 2000 World Series bid.

Cashman had to do some rare heavy lifting in 2000. Coming off back-to-back World Series titles, nothing in the Bronx looked the same as the millennium turned, except the names in the lineup card. This offense needed a wake-up call, big time.

Faced with the availability of a few big names (yes, Cashman considered Sammy Sosa), the Yanks ultimately pulled the trigger on former Braves and Indians rival David Justice, and he did not disappoint. It cost Ricky Ledee, Jake Westbrook, and Zach Day.

In 78 games, Justice triple-slashed .305/.391/.585 in the Bronx, rocking 20 homers and 60 RBI. And when the lights shone brightest, he punched New York’s ticket (token?) to the Subway Series, ruining Arthur Rhodes’ life in Game 6 of the ALCS.

He returned to the Boogie Down in 2001, but the magic was gone, and Justice retired after the 2002 season in Oakland.

But he’ll forever be the missing piece to a three-peat, whom Cashman uncovered when confronted with a number of options. Perfect fit.

1. Aroldis Chapman-Gleyber Torres Swap

Aroldis Chapman received his Chicago Cubs World Series ring, then went back to the Yankees.

The Aroldis Chapman gambit, beginning-to-end, was probably the most ruthless move of the Cashman era. It’s also set the Yankees up for their next decade of success. This one was a win-win-win-win.

The NYY acquired Chapman at a steep discount following the 2015 season, knowing he’d be facing a domestic violence-related suspension. The charges ended up being dropped, and Chapman missed 30 games, but he was acquired in exchange for Eric Jagielo (the guy picked before Aaron Judge), Caleb Cotham (now a coach!), Tony Renda, and Rookie Davis.

Months later, with the Yanks unable to repeat their magical 2015 Wild Card campaign and falling out of the race, Chapman was sent to the eventual World Champion Chicago Cubs, who were in desperate need of a closer and a workhorse. Despite blowing Game 7 of the World Series under great duress (Joe Maddon, what were you doing that series?), Chapman’s team picked him up in extras, and the deal worked out for Chicago!

Except, well…for that half-season, Cashman finagled GLEYBER TORRES, Billy McKinney, and Adam Warren in the deal. And at the conclusion of the World Series, Chapman cakewalked right back to the Bronx. Two months later, Cash had every piece of this deal back in pinstripes, and a future icon in Torres secured.

Talk about a masterwork.

Honorable Mentions

Brian Cashman has made so, so many great trades that don’t make the top five. Pour one out for these genius maneuvers.

2005: Shawn Chacon for Ramon Ramirez and Eduardo Sierra

2009: Curtis Granderson in a 3-Way for Austin Jackson, Phil Coke, and Ian Kennedy

2014: Didi Gregorius/Shane Greene Mega-Deal

2016: Justus Sheffield and Clint Frazier for Andrew Miller

2018: Luke Voit for Gio Gallegos and Chasen Shreve

2018: Zack (nee Zach) Britton for Josh Rogers, Dillon Tate, and Cody Carroll