As my esteemed colleague Rich Kaufman wrote on Tuesday, Brian Cashman deserves a lot of credit for the Aroldis Chapman trade. From the moment the Yankees bought low on him over the winter to the moment they sold high on him this week to the Cubs, the Yankees handled Chapman flawlessly.
Time will tell how the trade will actually work out, especially since it’s a much longer play for the Yankees than the Cubs. Even if Chapman pitches lights-out en-route to the Cubs first championship since Teddy Roosevelt was in office, the trade for the Yankees still has the potential to be one of the best in team history.
It got me thinking, where does this rank in the lengthy list of trades Brian Cashman has made during his tenure as Yankees General Manager?
The list starts off with a bang. The first significant trade Cashman made after receiving the keys to the Yankees Ferrari in 1998 was for Chuck Knoblauch. Despite Knobby’s yips, that trade worked out pretty well. A year later he traded away Mike Lowell, which Cashman has stated is his biggest regret as Yankees GM. Later in the same month he made a blockbuster trade within the division, bringing Roger Clemens to the Bronx in exchange for a package that included David Wells, Graeme Lloyd, and Homer Bush.
Not all the trades Cashman has made have the star power that Clemens-Wells does. There are a number of moves that amounted to nearly nothing for either side. Many involved the Yankees trading away young players with mild upside for last-ditch effort veterans. Some are slanted in the Yankees’ favor and some slanted in the opposing favor. There are no trades on the list, however, that have left Brian Cashman feeling embarrassed.
For all the praise Billy Beane receives, partially thanks to Hollywood, he did trade Josh Donaldson (who holds the second highest total WAR over the past three seasons in MLB, behind only Mike Trout) for a package headlined by Brett Lawrie. Brian Cashman may have higher expectations and a bigger checkbook to work with (although I have a theory Beane likes being the underdog, and would prefer to almost win than actually win) but no trade on Cashman’s resume is as egregious as the Donaldson swap. (Free Agents are another story, for another blog).
I’ve chosen to highlight some of the better trades of Cashman’s career where I think he actually swindled the opposing teams.
June 29, 2000: Yankees traded Ricky Ledee, Jake Westbrook and Zach Day to the Cleveland Indians for David Justice
Not only did David Justice truck-stick the opposing catcher in this YES Network throwback commercial (à la George Costanza with Bette Midler) but he also helped the Yankees win the World Series in 2000.
Justice was the Yankees best hitter in the second half of that season and helped rejuvenate a sputtering offense by hitting .305/.391/.585 with 20 long-balls in 78 games.
Looking back at the names the Yankees parted with, it’s not as if they got Justice for a bag of balls. Ricky Ledee was a nice fourth outfielder and only 26 years old when the Yankees traded him, but he never bested the .822 OPS he posted in 1999 (seriously, .822).
Westbrook and Day combined to win 126 big league games, and Westbrook was an All Star for the Indians in 2004, but other than that season in which he posted a 3.38 ERA, he never had another sub-4.00 ERA when he exceeded 100 innings in a season.
Considering the Yankees position in 2000, Ledee was never going to be more than a bench player. During the PED-era those were a dime-a-dozen (which might actually explain the .822 OPS). Day hung around the majors for 5 seasons but was also never going to have any long-term success with the Yankees. The only player you can argue the Yankees regret giving up is Westbrook, but I think if given a do-over, Brian Cashman would gladly trade him for the 2000 World Series trophy.
Still Michael Kay’s best home run call.
July 31, 2003: Yankees traded Brandon Claussen and Charlie Manning to the Cincinnati Reds for Aaron Boone
In 2002, Robin Ventura – who ironically the Yankees got in exchange for David Justice after the ’01 season – had a great year. He smashed 27 home runs and drove in 93 runs in 141 games for the Yankees, who were in desperate need of a third baseman after Scott Brosius retired.
In 2003, Robin Ventura did not have a great year. His OPS dropped 100 points and his ageing bones did not allow him to move very well at the hot corner.
On the day of the trade deadline in ‘03, Brian Cashman went to work. He first flipped Ventura to the Dodgers for Scott Proctor and Bubba Crosby (another solid trade) and then got Boone from the Reds in exchange for Claussen, a four-A starting pitcher, and Manning, who only pitched 42 innings at the big league level.
Aaron Boone’s impact on the Yankees during the regular season was marginal. While he certainly provided improved defense, his production at the plate was pedestrian (you could argue worse than Ventura’s). This trade is memorable, however, for two very important franchise-altering events that resulted from Boone coming to New York.
The first is obvious: Boone’s walk-off home run against Boston in the 2003 ALCS will go down as one of baseball’s most memorable. The second happened because Boone tore his ACL in a pickup basketball game during the offseason. He was slotted as the Yankees starting third baseman, but after the injury that would keep him out for the entire 2004 season, Cashman decided to trade for Alex Rodriguez. Opinions on the ARod trade will differ from fan to fan, but no one can argue that it didn’t alter Yankees history.
July 30, 2006: Yankees traded Matt Smith, C.J. Henry, Jesus Sanchez and Carlos Monasterios to the Philadelphia Phillies for Bobby Abreu and Cory Lidle
First of all, RIP in peace Cory Lidle. I still remember where I was the day I heard the news that Lidle died. My college roommate (a Mets fan) told me that Lidle crashed a plane into a NYC high-rise. I obviously didn’t believe him, since it was in his personality to make crap like this up from time to time (love the kid), but this time he was not joking.
Ok, onto the Abreu aspect of this trade. The Yankees desperately needed outfield help after both Hideki Matsui and Gary Sheffield suffered wrist injuries during the early months of the 2006 season. Cashman traded for Abreu and he immediately started raking. In 58 games, he had an impressive slash line of .330/.419/.507. He went on to have two more very productive years with the Yankees, averaging 40 doubles, 18 home runs, and 100 RBIs.
Who did the Yankees give up? Matt Smith turned out to be the highlight of the package for the Phillies; he pitched 12.2 innings for them over two seasons. Monasterios was the best major leaguer of the bunch (4.38 ERA in 88.1 IP), but he didn’t break into the bigs until 2010 with the Dodgers. Henry never made it past high-A ball and Sanchez, who’s position on baseball-reference is listed as “Pitcher and Catcher,” never cracked AAA.
Essentially the Yankees got an All Star right fielder, who had a debilitating fear of walls but keen plate discipline, and a starting pitcher, who if not for his love of flying dangerously close to tall buildings was in the Yankees’ future rotation plans, for a discarded pile of prospect garbage.
December 5, 2014: (3 team trade) Yankees traded Shane Greene to the Detroit Tigers in exchange for Didi Gregorius from the Arizona Diamondbacks
Do you remember April of 2015 when every Yankees fan on earth was destroying Cashman for trading Shane Greene, who had got off to a hot start with Detroit, for Didi Gregorius, who had got off to a slow start with the Yankees? Now that looks like one of the most lopsided trades in team history.
In exchange for a guy who posted a 6.88 ERA in 2015 and who has now been relegated to the Detroit bullpen, the Yankees got a 26-year-old shortstop who has turned into their best everyday player.
Since that rough April last year, Didi has completely transformed his game. He’s hit .283 with 66 extra base hits during that span, and this year leads the league with a .360 batting average against left handed pitching.
Didi Gregorius is not Derek Jeter, but then again nobody will ever be. He is however one of the only players on the current Yankees roster I would be upset if they traded. Not a bad return for a pitcher the majority of Yankees fans could not pick out of a lineup.
Some other thoughts:
- July 31, 2010: Yankees traded Matt Cusick and Andrew Shive to the Cleveland Indians for Kerry Wood: Only about a decade too late on Kerry Wood, Cash.
- December 16, 2003: Yankees traded Nick Johnson, Juan Rivera and Randy Choate to the Montreal Expos for Javier Vazquez… January 11, 2005: Yankees traded Javier Vazquez, Brad Halsey and Dioner Navarro to the Arizona Diamondbacks for Randy Johnson… December 22, 2009: Yankees traded Melky Cabrera, Mike Dunn and Arodys Vizcaino to the Atlanta Braves for Boone Logan and Javier Vazquez: I think Brian Cashman wishes he never came across the name Javier Vazquez.
- July 31, 2014: Yankees traded Kelly Johnson to the Boston Red Sox for Stephen Drew: #NeverForget
