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

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.

3. David Wells for Roger Clemens

Somehow, the Yankees managed to upgrade from David Wells.

Most general managers, coming off a 114-win regular season and World Series title, would probably rest on their laurels and hold onto their third-place Cy Young finisher.

Brian Cashman, even at a young age, was not most general managers.

Well aware of the backlash that would soon hit his windshield, Cashman saw a chance for a monumental upgrade when Roger Clemens exerted a clause in his Toronto deal that allowed him to force a trade if he deemed his squad to be non-competitive. Much to everyone’s consternation, the Yankees pounced, swapping David Wells, he of the 18-4 record and perfect game in 1998, to Toronto, along with Homer Bush and lefty Graeme Lloyd.

In exchange, the Yanks got the Rocket, and Wells immediately regressed in ’99 (though he made the All-Star Game and won 20 games in 2000) and possessed significant vitriol against Cash for forcing him out of town — though not enough to prevent his return to NYC in 2002.

Clemens, arriving in New York at the age of 36, struggled to a 4.60 ERA amid an offensive explosion in ’99, but regained his form in 2000, and won the 2001 Cy Young with a 20-3 mark. Clemens also cashed in on two World Series during his time in New York, his signature moment a 15-K, one-hitter in the 2000 ALCS in Seattle.

And speaking of 2000…

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