Yankees Trade Deadline: Remembering the best and worst deadline deals in Yankees history

The Yankees have declared their intention to be buyers at the trade deadline this year, as even though they are exactly a .500 team at the All-Star Break, the American League East has proved to be far from dominant this year. They sit five games behind the first-place Orioles and just one behind the second-place Blue Jays as they rest for a few days. Although they will be resting, it will probably not be a relaxing time for GM Brian Cashman and his team as they try to find the right fit for new players to bring into the fold and improve this team.

Trade Deadline deals can be quite a mystery, with the ultimate results of whether or not it was a good one staying unknown for years. Sometimes, they are clear winners, such as the Phillies and Rangers both acquiring Cliff Lee in 2009 and 2010 respectively for an unimpressive return. Other times, they are duds, like when the Red Sox sent a prospect named Jeff Bagwell away in 1990 in exchange for Astros reliever Larry Andersen. There are even deals that look smart in the short-term but long-term turn out to be a mixed result--the 1987 Tigers won the AL East with Doyle Alexander pitching to a 1.53 ERA in 11 starts down the stretch, but in exchange they lost a future Hall of Famer in 20-year-old John Smoltz. The Yankees have made all sorts of deals like these over the years, so which were some of the best and worst?

2000
David Justice for Ricky Ledee, Jake Westbrook, and Zach Day

The Yankees were going for a three-peat in 2000, but they were only a couple games over .500 in late June. Their left field production from Ledee and Shane Spencer had been poor too, batting a mere .256/.320/.421 with a collective wRC+ of 86 through the first half. Ledee had been a promising prospect and both Westbrook and Day had flashed potential in the minors, but Cashman decided to go ahead with this deal with the Indians on June 29th anyway. Justice was in the middle of a career-high 41-homer season, and he hit 20 of them in pinstripes, hitting .305/.391/.585 with a 145 wRC+ down the stretch for the Yankees as they rallied to win the AL East.

Justice also earned ALCS MVP honors with an eventual pennant-winning homer off the Mariners' Arthur Rhodes in Game 6, and the Yankees won their 26th World Series title. Justice slipped a little bit to about a replacement-level DH in 2001, though the Yankees still came within a couple outs of another title. He was traded to the Mets in the off-season for Robin Ventura. The three players traded all had varying degrees of success (especially Westbrook in Cleveland), but this was still a smart move to make.

1988
Ken Phelps for Jay Buhner

Obligatory:

There were a couple of other minor leaguers involved in the infamous July 21, 1988 trade that sent the budding slugger Buhner to the Mariners in exchange for Phelps, and I've written about the deal before. To keep it succinct though, the Yankees were in a tight race for the AL East and George Steinbrenner wanted to add some power to the lineup. However, it was pretty silly from the start to acquire another DH when they already had Jack Clark doing a fine job in the DH spot anyway. Phelps did hit 10 homers in 45 games the rest of the way with a 147 OPS+, but he was gone from August of the next season. The Yankees didn't make the playoffs, and Buhner went on to bash 310 homers in Seattle.

Preach, Frank Costanza.

1996
Cecil Fielder for Ruben Sierra and Matt Drews

I'd be very curious as to how fans today would react to this trade. The '96 Yankees were in first place when they made this trade, but they had received some of the worst DH production in the league from Sierra, who clashed with new skipper Joe Torre and also seemed to constantly whine about his place in the batting order. The offense on the whole was around league average, but GM Bob Watson wanted more dingers. Thus, they arranged a trade with the last-place Tigers for the slugging Fielder, who up to that point had outhomered everyone in the 1990s.

People today wouldn't have been upset about Sierra's departure, but given how much more fans seem to love prospects these days, they might have been irked by giving up Drews. The 13th overall pick by the Yankees in 1993, the 6'8" righty Drews was twice a Baseball America Top 100 Prospect and had actually been ranked 12th-highest in baseball prior to the '96 season. Even though he struggled in the first half of '96 for High-A Tampa and Double-A Jacksonville, he was still a highly respected prospect. Would people have been okay giving that up for a season and a half of production from a DH? Maybe so since Fielder was such a force at the time, but who knows?

Fortunately, it ended up working out brilliantly for the Yankees, as Sierra didn't do much in Detroit and Drews never made the majors. Fielder's bat ended up helping the Yankees win the AL East and eventually the World Series, where he hit .391/.440/.478 against the Braves and probably should have been named World Series MVP over John Wetteland. He declined in '97 and after departing as a free agent, was suddenly done with baseball by the end of '98. Regardless, that '96 trade was a steal for the Yankees.

1987
Steve Trout for Bob Tewksbury and two prospects

Classic Steinbrenner quote to then-manager Lou Piniella: "Lou, I've just won you the pennant. I got you Steve Trout!"

Trout was nothing like the unrelated Mike Trout in terms of baseball talent. The Yankees acquired him from the Cubs on July 13th, and he never won a game for them, pitching to an atrocious 6.60 ERA in 14 games and nine starts while the Yankees missed the playoffs for the sixth straight season. Tewksbury ended up being the star of the deal, as he went on to have a fine career with Cardinals, peaking in 1992 when he finished third in NL Cy Young Award voting with 6.5 WAR and a 158 ERA+. Whoops.

2006
Bobby Abreu and Cory Lidle for C.J. Henry and three prospects

Oh man, this deal. That move in 2006 pretty much cemented my admiration for Brian Cashman. The Phillies had been trying to pry better prospects out of Cashman for weeks in exchange for Abreu, an obvious fit for the Yankees since both Hideki Matsui and Gary Sheffield were hurt. Cashman stood his ground though, and eventually got Abreu and Lidle for essentially peanuts. The Yankees caught fire with Abreu and eventually won the division over Boston & Toronto, and they made the playoffs twice with him. In two and a half years with the Yankees, Abreu hit .295/.378/.465 with 95 doubles, 43 homers, and a 120 OPS+. Lidle was also a serviceable fifth starter until his tragic death just about a week after the Yankees were eliminated from the playoffs.

Henry was the 17th overall pick of the 2005 draft, but he just could not hit a lick. He quit baseball in '08, went back to college, and I later saw him playing college basketball in the NCAA Tournament with Kansas. Heh. None of the other three prospects (Jesus Sanchez, Carlos Monasterios, and Matt Smith) amounted to much of anything, either. Classic Ninja Cash.

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There are countless other memorable trade deadline deals that I didn't mention. (i.e. good: David Cone for Marty Jenzen and two prospects in '95, bad: Lance Berkman for Mark Melancon in 2010, etc.) Which deals are your favorite? Which deals do you regret the most?