Each team’s best and worst offseason trade of the last 20 years

During the winter, free agency is what gets most of the attention. And rest assured, we’ll be diving down that rabbit hole sooner rather than later. But teams also made blockbuster trades each winter to help turn their clubs into contenders for the next season and beyond. Just like we did back in July, we’re going to look at the best and worst trades made by each team over the past 20 years. This time, we’re going to look at those trades that went down from October to March – you know, the actual, legitimate offseason.

Just one caveat – just because a team gives up a lot, that doesn’t necessarily make it a “bad trade”. The Braves gave up a future ace in Adam Wainwright when they acquired J.D. Drew from the Cardinals, but Drew had the best season of his career in Atlanta, and was a legitimate MVP candidate. Maybe if Drew fell flat on his face, we’d include it, but that didn’t happen, so it’s not going to be on this list for the Braves.

And as usual, here are shortcuts to navigate by team in case you don’t want to dig.
Arizona – Atlanta – Baltimore – Boston – Chicago Cubs
Chicago White Sox – Cincinnati – Cleveland – Colorado – Detroit
Houston – Kansas City – LA Angels – LA Dodgers – Miami
Milwaukee – Minnesota – New York Mets – New York Yankees – Oakland
Philadelphia – Pittsburgh – St. Louis – San Diego – San Francisco
Seattle – Tampa Bay – Texas – Toronto – Washington

Enjoy the list.

Arizona Diamondbacks
Best trade: Acquired Miguel Batista and Orlando Hudson from Blue Jays for Troy Glaus and Sergio Santos (December 27, 2005)
Calling this the best offseason trade for the Diamondbacks might be pushing it a bit, but man…this franchise hasn’t exactly shined in the offseason. Orlando Hudson was the reigning AL Gold Glove winner at second base for the Blue Jays when Arizona brought him over, and Hudson responded by winning two more awards in the desert. He also made the 2007 All-Star Team as a Diamondback, and hit .294/.365/.448 in his three seasons with the club. When he signed with the Dodgers after the 2008 season, Arizona got the Dodgers’ first round pick, which was used to select A.J. Pollock, and a comp pick that turned into Matt Davidson, who was traded to the White Sox last winter for closer Addison Reed. Batista tossed a career-high 206 1/3 innings in 2006, and he turned into a comp pick named Ed Easley, who never made the majors, but is still kicking around the upper minors.

Going the other way was Glaus, who hit .256/.360/.496 and made $20.5 million in two years with the Jays before begin dealt to the Cardinals for Scott Rolen. Santos never broke through as a hitter with Toronto and bounced around the minors before being converted to a pitcher by the White Sox in 2009. The Sox dealt him back to Toronto before the 2012 season, and he’s thrown just 51 2/3 innings in three seasons since.

Worst trade: Acquired Shane Nance, Richie Sexson, and Noochie Varner from Brewers for Chris Capuano, Craig Counsell, Jorge de la Rosa, Chad Moeller, Lyle Overbay, and Junior Spivey (December 1, 2003)
A lot of people will probably argue for the Dan Haren trade, in which Arizona gave Brett Anderson, Carlos Gonzalez, and a few more players to the Athletics for Haren. But at least they got a good performance from him, and at least they dealt Haren for a solid return a couple of years later. They gave up six players, mainly for Sexson, and got *nothing* in production back. Sexson played just 23 game with Arizona, and while he hit .233/.337/.578, that was good for just a 126 OPS+ in 2004. Varner never made the majors, and Nance had a 5.84 ERA in 12 1/3 innings with the Diamondbacks. And while the Diamondbacks did get a pair of draft picks when Sexson signed with Seattle, they turned into Matt Torra (who never made the majors) and Micah Owings (4.69 ERA in 320 1/3 innings with Arizona).

Now, we’ll talk about what they gave up. No one was a star, but all six players made the majors with Milwaukee. Capuano had a 4.34 ERA in 744 2/3 innings with the club. Counsell hit .241/.330/.315 over 140 games in his one season with Milwaukee after the trade before heading back to the desert. Moeller played three years with Milwaukee as their backup catcher, hitting .204/.257/.319. Overbay shined in two seasons with the Brewers, hitting .289/.376/.464 with 35 homers before being traded to the Blue Jays when he moved into arbitration. de la Rosa struggled to a 6.23 ERA with the Brewers in 95 1/3 innings before being dealt to the Royals. Spivey hit .256/.337/.400 in 108 games with the Brewers.

The Sexson trade wasn’t a bad deal because the Diamondbacks gave up a future star or two – it was bad because they gave up a ton of depth for a guy that had a minimal impact on a club that would go on to lose 111 games. Why would Arizona trade Curt Schilling to the Red Sox for filler just days before bringing Sexson in? It boggles the mind. But hey, that disastrous season resulted in them taking Justin Upton first overall in 2005, which turned into another ugly trade before the 2013 season.

Atlanta Braves
Best trade: Acquired Tim Hudson from Athletics for Juan Cruz, Dan Meyer, and Charles Thomas (December 16, 2004)
This was a robbery, plain and simple – one of the few times that it looked like Billy Beane was had right from the getgo. Sure enough, none of the three players acquired by Oakland had any positive impact on the club. Cruz had a 7.44 ERA in 32 2/3 innings. Meyer had a 7.98 ERA in 44 innings. Thomas hit .109/.255/.109 in 55 plate appearances. Three players, and a total of about 215 innings of playing time. That includes the innings Thomas played in the outfield for Oakland, by the way.

Then, there’s Hudson. In his nine years with the Braves, he actually provided at least 215 innings of pitching for the club four times. In 1,573 innings on the hill, he pitched to a 3.56 ERA, and had an ERA of over 4.00 just once in those nine seasons. Yes, Hudson only made one All-Star team and received Cy Young votes in one season as a Brave, but Atlanta gave up absolutely nothing for him. That’ll do.

Worst trade: Acquired Keith Lockhart and Michael Tucker from Royals for Jermaine Dye and Jamie Walker (March 27, 1997)
This deal boggled my mind at the time because it came just days after the Braves traded starting outfielders Marquis Grissom and David Justice, presumably to clear some salary and a starting spot for Dye. It didn’t go that way, of course. Lockhart received way too much playing time from Bobby Cox over his Braves career, hitting .248/.312/.359 in a “utility role” that was really just him playing second base and pinch hitting. Tucker lasted two seasons with the Braves, hitting .265/.338/.433 in a fourth outfielder role before getting dealt to the Reds. Walker didn’t have much of a career with the Royals, pitching to a 6.71 ERA in 60 1/3 innings before putting together some good years in Detroit’s bullpen.

But Jermaine Dye was special. When the Braves traded him, he was only 23, coming off of a rookie season in which he homered 12 times in just 98 games and finished sixth in the NL Rookie of the Year voting. Dye struggled with a variety of injuries during his first two years with the Royals, but broke out in 1999, and became an All-Star in 2000 at just 26. He was dealt to Oakland in 2001, and eventually signed with the White Sox, where he continued to shine before retiring in 2009. After the Braves traded Dye, he hit .274/.340/.490 with 313 home runs over his major league career, which would run for another 13 seasons. But hey, at least Atlanta got bench depth!

Baltimore Orioles
Best trade: Acquired Tony Butler, Adam Jones, Kam Mickolio, George Sherrill, and Chris Tillman from Mariners for Erik Bedard (February 8, 2008)
Was there really any doubt? The Orioles dealt the talented, but oft-injured, Bedard to Seattle after the the best season of his career. Bedard proceeded to toss a whopping 255 1/3 innings over his time in Seattle. That might not sound too bad until you realize Bedard spent four seasons contracted to the Mariners, and made a total of 46 starts over those four years. He missed all of 2010, and made 16 starts in 2011 before being traded to the Red Sox. When he was actually on the mound, Bedard was fantastic, pitching to a 3.31 ERA, striking out 249, and walking 101. However, he simply wasn’t on the mound nearly enough to be worth half of the package that went to Baltimore in exchange for him.

Butler and Mickolio ended up as filler in the deal, as the former never made the majors and the latter pitched to a 4.32 ERA in 25 innings wearing the black and orange. He was traded to the Diamondbacks as part of the Mark Reynolds deal a couple of seasons later. Sherrill pitched well in his two years with the Orioles, making the 2008 AL All-Star Team, notching 51 saves and a 3.71 ERA in 94 2/3 innings before being traded to the Dodgers.

Jones and Tillman were, obviously, the stars of the return. Tillman was an All-Star for the Orioles in 2013, and has come into his own in the last three seasons after struggling in his first three years with the team. Since 2012 Tillman has tossed 499 2/3 innings with the Orioles, pitching to a 3.42 ERA while striking out 395. He’s just 26, and won’t be a free agent for another three seasons. Jones has turned into the face of the Orioles franchise, winning four Gold Glove awards, making four All-Star Teams, winning a Silver Slugger, and finishing in the top 15 of AL MVP voting three times. With the Orioles, he’s hit .281/.322/.465 with 166 homers and 76 stolen bases. The 29-year old is signed through the 2018 season, and the Orioles would take him over Bedard any day of the week. Throw in everyone else, and this trade is a slam dunk steal for Baltimore.

Worst trade: Acquired Sammy Sosa from Cubs for Dave Crouthers, Mike Fontenot, and Jerry Hairston (February 2, 2005)
This is one of those trades where the Orioles didn’t exactly give up a lot, didn’t eat the bulk of the remaining contract they acquired in the deal, and still wound up worse for the wear. Baltimore only paid Sosa $8.15 million in 2005 after this trade, with the Cubs eating the remaining $8.85 million of his salary, plus another $8 million in severance and assignment payments. And the players the Orioles gave up didn’t become superstars – Crouthers never reached the majors, and Fontenot and Hairston were bench players.

But Sosa just was not good with the Orioles in 2005, what would prove to be his penultimate year in the majors. In 102 games, he hit just 14 homers in 102 games, putting together a .221/.295/.376 line. His defense in the outfield, never a strong suit, was a nightmare. He was worth -1.3 fWAR for the year, and did all of that at a cost of $8 million and a trio of players. Sosa would be the last full-time right fielder the club had before installing a potential-laden 22-year old named Nick Markakis. So hey, at least the end of Sosa’s tenure in Baltimore has a bright spot.

Boston Red Sox
Best trade: Acquired Pedro Martinez from Expos for Tony Armas and Carl Pavano (November 18, 1997)
It took two players – just two! – to acquire the reigning NL Cy Young winner. Is this madness, or what?  To their credit, Armas and Pavano actually turned into pretty decent pitchers. Armas spent eight years with the Expos franchise, including two after the club moved to Washington. In 820 1/3 innings, Armas pitched to a 4.45 ERA. However, he missed large chunks of time in each year from 2003-2005, and never truly lived up to his potential. Pavano had a 4.83 ERA in 452 2/3 innings over parts of five seasons with Montreal, and was traded to the Marlins as part of an eight player trade that brought Cliff Floyd back to the Expos.

Martinez, of course, is one of the best pitchers of all-time, and is in line to earn induction to the Hall of Fame in 2015. Pedro spent seven years in Boston, went 117-37, pitched to a 2.52 ERA, tossed 1,383 2/3 innings, struck out 1,683 hitters, walked 309, won three AL Cy Young awards, made five All-Star Teams, and finished in the top five of MVP voting twice. His 1999-2003 stretch in Boston is one of the best runs we’ve ever seen from a pitcher in baseball history, and all it cost the Red Sox was a couple of pitching prospects and (of course) money to keep him in town.

Worst trade: Acquired Adrian Gonzalez from Padres for Reymond Fuentes, Casey Kelly, Eric Patterson, and Anthony Rizzo (December 6, 2010)
The Red Sox had their eye on Gonzalez for awhile, and when they finally acquired him from the Padres, it seemed like they’d be set at first base for the foreseeable future, especially after they gave him a mammoth seven-year contract extension. Of course, it didn’t work that way. Gonzalez put together an MVP caliber 2011, but Boston’s late season collapse ended all hopes of a playoff berth. Gonzalez struggled out of the gate in 2012, and was dealt to the Dodgers in August along with Josh Beckett, Carl Crawford, and Nick Punto. After just 282 games, Boston once again had a hole at first base, which they’d eventually fill with Mike Napoli en route to a World Championship in 2013.

The prospects they gave up for Gonzalez have been a mixed bag. Fuentes only received 36 plate appearances in the majors with the Padres before he was traded to the Royals last month. Kelly made just six starts in the majors in 2012, missed all of 2013 following Tommy John surgery, and returned to throw only 20 1/3 innings in the minors this year. Patterson received 104 plate appearances with the Padres in 2011 before being released at the end of that season. Rizzo struggled as a 21-year old to the tune of a .141/.281/.242 line with the Padres before being traded to the Cubs for Andrew Cashner and blossoming into a superstar in 2014.

I guess the Gonzalez trade did work out at the end of the day for the Red Sox – they won a World Series less than three years after it happened. But you have to wonder how their future would look had they never even made this deal in the first place.

Chicago Cubs
Best trade: Acquired Derrek Lee from Marlins for Hee-Seop Choi and Mike Nannini (November 25, 2003)
Remember when Hee-Seop Choi was going to be the next big first base slugger? Ah…good times. Choi hit eight  homers in 80 games with the Cubs in 2003, and was dealt to the Marlins with minor league pitcher Mike Nannini for veteran first baseman Derrek Lee. Choi would total just 784 plate appearance with the Marlins and later, the Dodgers, hitting a total of 30 homers with those two clubs. He last appeared in the majors in 2005, and has been playing with the Kia Tigers of the KBO since 2007.

Lee was the prize in the trade that sent Kevin Brown from the Marlins to the Padres in the winter of 1997, and he had been a fixture in Florida’s lineup since. But I don’t think anyone saw the breakout he had with the Cubs happening. From 2004 to his trade to Atlanta in the summer of 2010, Lee hit .297/.378/.527 with Chicago, blasting 179 homers in 924 games. He made a pair of All-Star Teams with the Cubs, won a pair of Gold Gloves, and was third in the 2005 NL MVP voting. That year, he led the National League in hits, doubles, batting average, and OPS while ranking second in baseball with 46 homers. Now that’s (roughly) $76 million and a pair of failed prospects well-spent .

Worst trade: Acquired Juan Pierre from Marlins for Sergio Mitre, Ricky Nolasco, and Renyel Pinto (December 7, 2005)
Two years later, the Cubs and Marlins would make another deal that didn’t end so well for Chicago. Pierre would do his typical Juan Pierre thing in 2006 with the Cubs, playing in all 162 games, leading the National League with 204 hits, and stealing 58 bases. Of course, his .717 OPS was good for just an 82 OPS+, and Pierre left town as a free agent that winter. He signed with the Los Angeles Dodgers, and the Cubs received a compensation pick that turned into a fellow named Josh Donaldson. Of course, Donaldson never played in a game above A-ball with the Cubs and was part of the ugly Rich Harden trade a year later, but hey, Josh Donaldson!

Mitre and Pinto had forgettable tenures in Miami – Mitre pitched to a 4.88 ERA in 190 innings with the club before being released, and Pinto had a 3.62 ERA in 231 innings over five years with the Marlins before he got his walking papers in 2010. Nolasco was the real gem, of course. In his eight years with Miami, he pitched to a 4.44 ERA and struck out 1,001 in 1,225 2/3 innings, making 30 starts five times in those eight years. He was traded to the Dodgers in 2013, and signed as a free agent with the Twins last winter. From 2006 to 2013, the Cubs only had three pitchers clear the 700 inning mark – Ryan Dempster, the embattled Carlos Zambrano, and the oft-injured Ted Lilly. Nolasco sure would have looked good eating up innings alongside of those guys.

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