Remembering the Yankees’ best and worst trade deadline deals

The Yankees have historically been an active trade deadline team, usually buying pieces to help a playoff run. With the team looking at a similar philosophy this year, let’s take a look back at some of the Bombers’ biggest trade deadline hits and misses.

Best Trade Deadline Moves:

David Cone (1995)

For my money, acquiring Cone in 1995 was the Yankees’ best deadline move ever. Cone had just won the Cy Young the year before, and posted similarly strong numbers for the Blue Jays in 1995. After the Yankees got him, he went 9-2 that season and became a legacy Yankee for his performance down the stretch and for years to come, winning four World Series and throwing a perfect game.

Two of the three pieces the Yankees sent to Toronto never made it to the bigs, and the other (Marty Janzen) pitched just 27 games. This was an all-time steal.

David Justice (2000)

The Yankees were treading water around .500 when they acquired Justice in June 2000. While his addition wasn’t the only thing that led the Yankees to a dramatic turnaround that ended in a championship, he sure did a lot. Justice hit 20 home runs and had 60 RBI in just 78 games, and won ALCS MVP en route to the World Series.

The Yankees gave up Ricky Ledee, Jake Westbrook and Zach Day in the deal, and while each had major league careers, the Yankees wouldn’t have won it all in 2000 without Justice.

Bobby Abreu (2006)

One of Brian Cashman’s all-time steals, adding Bobby Abreu in 2006 made the Yankees’ lineup a historic group of mashers. Just look at this lineup!

1. Johnny Damon, CF
2. Derek Jeter, SS
3. Bobby Abreu, RF
4. Alex Rodriguez, 3B
5. Jason Giambi, 1B
6. Gary Sheffield, DH
7. Hideki Matsui, LF
8. Jorge Posada, C
9. Robinson Cano, 2B

Unfortunately, the team’s pitching cost them during Abreu’s tenure in the Bronx, but he more than held his own. He was one of the most productive Yankees from 2006-2008, and the four prospects the Yankees gave up to get him didn’t amount to anything.

Three trades in 2016

The Yankees were in the rare position to sell in 2016, and they capitalized on a seller’s market. They turned Aroldis Chapman into Gleyber Torres, Adam Warren and two minor leaguers, Andrew Miller into Clint Frazier, Justus Sheffield and two prospects, and Carlos Beltran into three pitching prospects.

The Yankees won all three trades. By later signing Chapman, they took everything from Chicago for nothing but a three-month rental. Sheffield helped the Yankees get James Paxton, and while Frazier has had his ups and downs, he could also turn into something more via trade. The moves became a turning point for the Yankees’ organization.

David Robertson, Todd Frazier and Tommy Kahnle (2017)

Although the Yankees fell a touch short in 2017, the blockbuster that netted the team Robertson, Frazier and Kahnle was an “all-in” move. Robertson was stellar for the next season as well, Frazier was crucial to the 2017 team’s clubhouse vibe and on-field power, and Kahnle is still producing for the Yankees today.

Meanwhile, none of the three prospects Cashman dealt to Chicago have made the big leagues yet.

Worst Trade Deadline Moves:

Ken Phelps (1988)

Before the age of analytics, the Yankees were more prone to impulse trades. Phelps didn’t do much as a Yankee, but the man they traded to get him, Jay Buhner, became a slugger on the 1990s Seattle Mariners. I’ll let Frank Costanza take it away:

Jeff Weaver (2002)

The mid-2000s Yankees teams never had enough pitching, and Jeff Weaver was a desperate attempt to fill a hole. He was OK for Detroit before, but totally bombed as a Yankee, putting up a 5.35 ERA as a member of the team, and taking a loss in a 2003 World Series game.

Lance Berkman (2010)

After the thrills of the 2009 World Series, the 2010 team was almost as good in the regular season, but choked in the playoffs. Berkman was supposed to add thump to a solid lineup, but only hit one home run and barely posted a .700 OPS as a Yankee. His acquisition wasn’t even that necessary with Mark Teixeira already at first base.

Making matters worse, the Yankees traded Mark Melancon in the deal, who became a three-time All-Star reliever.

Four trades in 2014

2014 was a year best remembered as Derek Jeter’s last, but the Yankees tried to bolster the roster by adding Chase Headley, Brandon McCarthy, Stephen Drew and Martin Prado to the team down the stretch. While none of them were bad (except Drew), they just weren’t what the team needed.

The 2014 haul was more of a missed opportunity than anything else. If the team had gone for one big star instead of adding four mid-range players, the result may have been different.

Sonny Gray (2017)

Though the Yankees nailed their other 2017 deadline deal, trading for Gray was an unmitigated disaster. He was never comfortable as a Yankee, and failed to live up to the lofty expectations that preceded his arrival. He’s been better this year in Cincinnati, but will never again be the budding ace he once was.

Honorable Mentions:

These guys weren’t truly best or worst moves, but fell somewhere in between. However, they’re still worth mentioning.

Ichiro Suzuki (2012)

Acquiring Ichiro was undoubtedly one of the Yankees’ coolest moves, and while he was awesome that year, the team fell short of expectations and he declined over his next two years with the team. Still, he’s a fan favorite and it was special that he got to play as a Yankee.

Alfonso Soriano (2013)

The 2013 season was a season from hell for Yankees fans, but re-acquiring Soriano was an awesome consolation. His 17 home runs and 50 RBI in 58 games was David Justice-esque, but he fell off the next season and retired. His team didn’t make the playoffs, but Soriano and his power was heroic as a second-time Yankee.

Zack Britton and J.A. Happ (2018)

The jury is still out on these guys. Although they more than did their jobs last year, both have declined somewhat this season, particularly Happ. Much like in 2014, these players were fine that season, but were not the big splash the team needed to get over the hump. Not trading for an ace last season could haunt the team for years to come.