As Erik Bedard retires, a look at century's most lopsided trades

As Erik Bedard retires, Cliff Corcoran looks back on the deal that sent him from Baltimore to Seattle and transformed the Orioles, and where the trade ranks among the most lopsided of the last 15 years.

Erik Bedard retired on Thursday, cutting short another in a long string of rehabilitation efforts. The final blow was a strained back muscle suffered in spring training with the Dodgers, the seventh and final team to hope that the lefthander’s talent would win out over his fragility and poor control. There was a brief moment last decade when Bedard, armed with a low- to mid-90s fastball and a devastating curve, was considered one of the best pitchers in baseball. In 2007, he struck out 221 men in just 182 innings for the Orioles, leading the majors with 10.9 strikeouts per nine innings, going 13–5 with a 3.16 ERA (good for a 146 ERA+) and finishing fifth in the American League Cy Young voting. His player comment in the following spring’s Baseball Prospectus annual concluded with this:

"The only reason not to think of Bedard as a favorite for the 2008 Cy Young is the lack of support he’s likely to get from the Orioles. Amazingly, he’s been mentioned in trade talks; it should take a truly extraordinary package of players to get him."

During the short window between that book (which I edited) going to press and hitting the shelves, Bedard was indeed traded. That trade did indeed deliver Baltimore an extraordinary package of players that will be Bedard’s enduring legacy in the game.

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On Feb. 8, 2008, the Orioles traded Bedard to Seattle for a package of five players, including lefty reliever George Sherrill, a trio of pitching prospects (righty Chris Tillman, lefty Tony Butler, and reliever Kam Mickolio) and a 22-year-old centerfielder named Adam Jones who had played 73 games for the Mariners over the previous two years. Butler quickly washed out of the minors and Mickolio has found greater success as a closer in Japan than he ever did in the major leagues. But Sherrill made the All-Star team as the Orioles' closer in '08 before being traded for prospects at the '09 deadline, and Jones and Tillman have since emerged as arguably the best everyday player and pitcher on the first Baltimore playoff teams since the late 1990s.

Tillman has had a lousy 2015 thus far, due in part to back problems, but over the last three seasons, two of which ended with playoff berths for Baltimore, he led all Orioles pitchers with 200 or more innings pitched in ERA (3.42), ERA+ (117), WHIP (1.20), strikeouts (395), opponents’ OPS+ (90), wins (38), and winning percentage (.704). His 8.5 Wins Above Replacement over those three seasons also led all Orioles pitchers. The team's overall leader in WAR over those three seasons, meanwhile, was Jones, with 12.8.

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In the wake of the trade, Jones has emerged as one of the game’s true stars, making his first All-Star Game and winning his first Gold Glove in 2009, which was also his first above-average season at the plate. He added three more of each in the last three seasons to go with a Silver Slugger in '13 and a collection of MVP votes, including a sixth-place finish, in '12, the year the O’s broke their 14-year playoff drought. Jones has also distinguished himself off the field as one of the faces of the game, both through endorsements and in crucial moments such as April’s Baltimore riots, when the Orioles were forced to cancel two games and play a third in an empty stadium. Jones spoke thoughtfully and honestly before that game, then went out and drove in the first run in an 8–2 Orioles win.

I tend to think of Jones as a slightly overrated player on the field (I won’t dispute his value to the game or the Orioles off the field). Highlight plays aside, he has not been a worthy Gold Glove winner, and his low on-base percentages undermine the value of his powerful bat. I do not deny, however, that he is valuable. When he signed a six-year extension with the Orioles in May 2012 amid a typically hot start, I projected him as a .290/.330/.490 hitter going forward. Through Thursday’s action, he has hit .287/.323/.490 since the start of the '12 season, which translates to a 122 OPS+. Among players with 2,000 or more plate appearances over that span, that ranks Jones 19th in OPS+, but all but six of the players above him are corner outfielders, first basemen or designated hitters (the exceptions: Mike Trout, Andrew McCutchen, Buster Posey, Robinson Cano, Adrian Beltre and Matt Carpenter). In terms of WAR over that span, Jones ranks tenth among all hitters with 15.0 in three-plus seasons.

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​Bedard, meanwhile, made just 30 total starts in the three seasons following the trade due primarily to shoulder injuries, including an August 2009 labrum surgery that wiped out his entire '10 season. After his return in '11, the Mariners traded him to the Red Sox in a three-team deadline deal with the Dodgers that ultimately had no lasting impact on any of the three teams involved. From there, Bedard spent time with the Pirates, Astros, Rays, and Dodgers, battling poor control and injuries. He never again qualified for the ERA title, let alone recaptured his former promise.

Given the pivotal roles Jones and Tillman have played in Baltimore’s return to relevancy, it’s no exaggeration to call the Bedard trade a transformative one for the Orioles. In fact, it stands as one of the best trades in franchise history, as well as one of the best by any team in the 21st century. With Jones just 29 and under contract through 2018 and Tillman just 27 and under team control through '17, it seems likely to only gain ground in those rankings over the next few years.

As for where it stands now, I’ll turn to a simple methodology I’ve used before to determine the greatest deadline deals of all-time, first in Baseball Prospectus’s It Ain’t Over ‘Til It’s Over, then again a few years ago over at SB Nation. Quite simply, I calculate the remaining career bWAR totals for the players involved in the trade from the date of the trade forward and figure out which team came out ahead. The idea is to simplify the calculation and credit the teams for future production acquired, regardless of whether or not that production actually came in the given team’s uniform.

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By that method, the greatest trade in Orioles history was the one that sent veteran righty Mike Boddicker to the Red Sox at the 1988 deadline for 24-year-old Brady Anderson and 21-year-old Curt Schilling. That trade netted the Orioles 101.2 bWAR in future production. Barely more than two years later, however, general manager Roland Hemond, the same man who acquired Schilling, traded him to the Astros with Steve Finley and Pete Harnisch for veteran first baseman Glenn Davis, which cost Baltimore a whopping 140.7 bWAR in future production. That makes it difficult to credit the Orioles for acquiring Schilling, who was worth just 0.3 bWAR in his two-plus seasons there, though the O’s did still net 20.5 bWAR on Anderson vs. Boddicker alone.

Next on the list is the Orioles' acquisition of Ken Singleton and righty Mike Torrez from the Expos in December 1974 for a trio of players, none of whom would exceed replacement level in the majors after the trade. Torrez spent one strong season in Baltimore's rotation before being traded to Oakland in the deal that brought Reggie Jackson to the O's for his lone season in orange and black. Singleton, however, was a key piece of the Orioles' lineup for the next decade. He hit .290/.396/.456 (141 OPS+) over his first nine years in Baltimore, making three All-Star teams and twice finishing in the top three in the MVP voting. He also helped the Orioles reach what remain their last two World Series in 1979 and 1983 and win what remains their last championship in the latter season.

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The Orioles netted 50.3 bWAR in the Singleton trade, but next on the list is the Bedard trade, which has thus far provided Baltimore with 32.1 bWAR. That places the Bedard trade ahead of the Frank Robinson-for-Milt Pappas (and others) deal prior to the franchise’s breakout 1966 season (21.9 net bWAR); the ten-player trade with the Yankees at the '77 deadline that brought mainstays Scott McGregor, Rick Dempsey, and Tippy Martinez to Baltimore (25.7 net); and the underrated lean-years acquisition of Melvin Mora from the Mets for an aging Mike Bordick (22.4 net). Depending on how you view the Schilling acquisition, the Bedard trade thus rates as no worse than the third-best trade in Orioles history, and could arguably be considered the second-best based on production already banked despite the fact that the two key players acquired are still in their twenties.

As for where the trade ranks among all twenty-first century trades, here are the leaders in future production acquired according to my method:

1. 75.8 bWAR – Cleveland acquires Cliff Lee, Brandon Phillips, Grady Sizemore and Lee Stevens from Expos for Bartolo Colon and Tim Drew (June 27, 2002)

2. 53.6 bWAR – Padres acquire Adrian Gonzalez, Chris R. Young and Terrmel Sledge from Rangers for Adam Eaton, Akinori Otsuka and Billy Killian (Jan. 6, 2006)

3. 46.0 bWAR – Brewers acquire Lyle Overbay, Craig Counsell, Jorge De La Rosa, Chris Capuano, Junior Spivey and Chad Moeller from Diamondbacks for Richie Sexson, Shane Nance and Noochie Varner (Dec. 1, 2003)

4. 45.5 bWAR – Athletics acquire Dan Haren, Daric Barton and Kiko Calero from Cardinals for Mark Mulder (Dec. 18, 2004)

5. 38.8 bWAR – Cubs acquire Aramis Ramirez and Kenny Lofton from Pirates for Jose Hernandez, Bobby Hill and Matt Bruback (July 23, 2003)

6. 37.1 bWAR – Rangers acquire Adrian Gonzalez, Will H. Smith and Ryan Snare from Marlins for Ugueth Urbina (July 11, 2003)

7. 34.0 bWAR - Yankees acquire Alex Rodriguez from Rangers for Alfonso Soriano and Joaquin Arias (Feb. 16, 2004)

8. 32.8 bWAR – Blue Jays acquire Jose Bautista from Pirates for Robinzon Diaz (Aug. 25, 2008)

9. 32.7 bWAR – Astros acquire Carlos Beltran from Royals for John Buck and Octavio Dotel* (June 24, 2004)

10. 32.1 bWAR – Orioles acquire Jones, Tillman, Sherrill, Mickolio and Butler from Mariners for Bedard

*This was a three-way trade. Dotel went to the A’s and the Royals got Mark Teahen and Mike Wood from Oakland. With Beltran still active, the Royals have thus far lost 34.6 bWAR in future production

With Beltran and Rodriguez close to the end of the line and Ramirez retiring at season’s end, the Bedard trade should surpass both of those deals in the next couple of years. Given the relative ages of the players involved, it seems likely to pull ahead of the Bautista trade as well and could even catch the Rangers’ acquisition of Gonzalez, which was made by John Hart and then quickly undone by Jon Daniels within months of the latter’s hiring.

Though it only ranks ninth above, the Bedard trade could qualify as one of the five most lopsided trades of the last 15 years (though watch out for the Cubs’ acquisition of Anthony Rizzo from the Padres, which is already 9.3 bWAR in the Cubs’ favor as Andrew Cashner continues to struggle to fulfill his potential). Credit then-Orioles president of baseball operations Andy MacPhail for seeing in Bedard a control-challenged pitcher with a problematic injury history entering his age-29 season rather than the up-and-coming Cy Young candidate on which much of the rest of the league was dreaming. That trade, more than any other single move, altered the course of Orioles history.