MLB Trade Deadline: Worst Red Sox deals in history
A painful reminder of the worst trade deadline deals that the Boston Red Sox have ever made.
The MLB trade deadline is rapidly approaching, leaving the Boston Red Sox little time to make the type of significant upgrade to the roster that could become a difference maker in a tight division race.
Red Sox Nation is imploring Dave Dombrowski to make a splash with another bold move that he’s become famous for. The win-now mentality in Boston drives the temptation to empty the cupboard of their stacked farm system to bring in a star caliber player that improves the team’s chances of winning the World Series in 2016.
Sacrifice tomorrow for today.
Sometimes these decisions actually work, as the list of recent champions is littered with teams that made crafty moves to upgrade at the deadline. Last year it was the Kansas City Royals, who needed an ace to front their rotation and acquired Johnny Cueto to fill that void. While Cueto didn’t live up to his lofty standards during his time in the American League, he was still a massive upgrade over their alternative options and proved to be enough to put the Royals over the top.
This is the time of year where teams are forced into two camps – buyers and sellers. The Red Sox have been both at various times throughout their storied history, but there are a number of occasions when they should have been neither. Whether it was a botched attempt to upgrade the roster with a player that never panned out, a prospect they surrendered that turned out to be far too valuable to have let go or an attempt to sell that didn’t bring back the return they expected, the Red Sox have made their fair share of bad trades over the years.
Sometimes the best moves are the ones you don’t make. Here is my list of the mid-season trades that the Red Sox should have thought twice about.
Next: Gagne
David Murphy for Eric Gagne – 2007
On their path to another championship, the Red Sox looked to upgrade their bullpen at the 2007 deadline by adding former Cy Young winner Eric Gagne.
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The three-time All-Star was once one of the most dominant relievers in the game. During his peak from 2002-2004 he ripped off a record streak of 84 consecutive saves, including a league-leading 55 in 2003 that fell two shy of the single-season record for consecutive saves. Sounds like the type of security any team would wish for at the back end of their bullpen, right?
Except that the Red Sox already had an All-Star closer by the name of Jonathan Papelbon, who made it clear to the front office that he would not be pleased with conceding the role to Gagne. In a related story, this would not be the last time Papelbon would be viewed as not being a “team player.”
Gagne agreed to move into a setup role in Boston, but never looked comfortable in it. He produced an unsightly 6.75 ERA over 18 2/3 innings to close out the regular season and memorably blew Game 2 of the ALCS against the Cleveland Indians.
The Red Sox went on to win a title in spite of Gagne’s presence in the bullpen, but that doesn’t save the Gagne trade from being a terrible decision.
The spare parts that Boston gave up in the deal, Engel Beltre and Kason Gabbard, never amounted to much but Murphy had a decent career after breaking in with the Texas Rangers. He may not have reached the ceiling of the top prospect status he had in the Red Sox organization, but he enjoyed a solid 10 year career in which he produced a .274/.333/.432 line. That’s a lot more value than Boston got out of Gagne.
The Red Sox were clearly enamored with Gagne’s save record, but someone should have saved them from making this disastrous deal.
Next: Suppan
Freddy Sanchez for Jeff Suppan – 2003
Freddy Sanchez was once one of the top infield prospects in the Red Sox system, but with Nomar Garciaparra locked in at shortstop the team felt that Sanchez was expendable. They needed to add an arm to their rotation, so they sent Sanchez and reliever Mike Gonzalez to the Pittsburgh Pirates for a package headlined by Jeff Suppan.
Suppan was originally drafted by the Red Sox, but management must have forgotten the 5.99 ERA he produced during his first three years in Boston. Or the four years after that where the results weren’t much better pitching for the Kansas City Royals. All they looked at was that current season, where a move to the National League improved his fortunes to the tune of a 3.57 ERA through 21 starts.
Prior to that, Suppan had been nothing more than a back of the rotation innings-eater. He did have five straight seasons in which he pitched 200+ innings. They just weren’t good innings.
Boston clearly thought that the then-28-year old had turned a corner, but they were quickly proven wrong. Suppan posted a 5.57 ERA in 11 appearances (10 starts) for the Red Sox to finish the season before quickly scampering back to the NL the following year.
Meanwhile, Sanchez would become a three-time All-Star for the Pirates and won a batting title in 2007. The Red Sox ended up trading Nomar a year later and spun through a seemingly endless cycle of shortstops that lasted until Xander Bogaerts put an end to the revolving door at the position.
Next: Lester
Jon Lester and Jonny Gomes for Yoenis Cespedes – 2014
After winning the World Series in 2013, the Red Sox found themselves as sellers at the deadline the following season. Jon Lester was in the middle of a career year with free agency looming, so when extension negotiations stagnated the front office decided to trade their ace to the Oakland Athletics for Yoenis Cespedes, who came with an extra year of control.
Many fans blame the low-ball $70 million offer the Red Sox insulted Lester with as the reason why he’s no longer in Boston, but that’s not entirely true. All that did was set contract talks aside until after the season, but it was the trade the ultimately cost the Red Sox their best pitcher.
Had he remained with the team through the rest of that season then Boston would have entered free agency as the heavy favorites to retain Lester. The previous regime wasn’t willing to go as far as the Chicago Cubs did for an over-30 starter, but all they had to do was give him an offer in the same ballpark. Lester had indicated a willingness to take a hometown discount to remain in Boston, but that went out the window after he was traded. By his own admission, leaving Boston to sign as a free agent elsewhere would have been very difficult for him to do, but this trade gave Lester the opportunity to experience another city for the first time in his career. Deciding not to return after being traded turned out to be easier than bolting as a free agent would have been if he hadn’t already left.
The trade itself brought back what seemed like relatively fair value at the time, as Cespedes gave them an All-Star caliber power-hitting outfielder, but it didn’t take long for buyer’s remorse to set in. Cespedes hit only 5 home runs in 51 games for the Red Sox, while posting a sub-.300 on-base percentage. The cannon of an arm he’s known for was wasted playing in Fenway Park’s shallow left field and he made a habit of mental lapses on defense that overshadowed his natural abilities.
It only took two months for the Red Sox to tire of Cespedes, who they traded in the offseason to the Detroit Tigers for Rick Porcello. That deal appeared to be in danger of becoming among the worst in franchise history as well after a disastrous 2015 season for Porcello, but he’s turned his career around this year. Porcello is clearly no Lester, but he is tied for the league lead in wins while posting a 3.47 ERA reminiscent of a typical Lester season when he was here.
Porcello’s career year doesn’t make up for the Lester trade, but it at least mitigates the damage when you consider the Red Sox likely wouldn’t have him in the rotation if they hadn’t dealt Lester for the chip that brought Porcello to Boston. That’s the only reason why the Lester deal isn’t higher than the next ill-fated trade on this list…
Next: Lackey
John Lackey for Allen Craig and Joe Kelly – 2014
Losing John Lackey doesn’t hurt nearly as much as losing Lester did, but this trade ended up as the worse of the two given the return.
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Lackey bounced back from a lost 2012 season to become the pitcher the Red Sox had always hoped for, but his contract situation put the team in a position where they felt they had to deal him. A clause in his deal stipulated that if Lackey missed significant time with a pre-exiting medical concern, which he did, then a team option at the league minimum price would be tacked on for 2015. Lackey threatened to retire rather than honor this stipulation, but instead of calling his bluff the Red Sox opted to deal him to the St. Louis Cardinals.
Of course Lackey ended up pitching for the Cardinals in 2015 for the bargain price of $507,500 and had an outstanding season, which he parlayed into a lucrative new deal this year to join old friend Jon Lester in Chicago.
In return the Red Sox received Allen Craig and Joe Kelly, neither of whom have provided much value to the team, while each has spent significant time in the minors. Craig is being paid $20 million over the next two seasons despite having been moved off of the 40-man roster, while Kelly has been converted into a middle reliever after several failed attempts to stick in the rotation.
Next: Schilling
Curt Schilling and Brady Anderson for Mike Boddicker – 1988
The Red Sox were looking for an established veteran starter with postseason experience and ended up getting exactly that from Mike Boddicker. The deal worked out pretty well in the short term, but this is a classic example of why pushing your chips in to win now can backfire in the long run.
Boddicker went 7-3 with a 2.63 ERA down the stretch for the Red Sox to help get them to the postseason, but was lit up for 6 runs in a loss to Oakland in the ALCS. He followed that with two more solid seasons, going a combined 32-19 with a 3.66 ERA to wrap up his tenure in Boston.
Not bad for a trade deadline acquisition. What the Red Sox got out of Boddicker isn’t what makes this a regrettable deal, it’s what they gave up for him. It may have taken a few years to realize what they lost, but in retrospect the Red Sox ended up giving up a very valuable prospect that they would have been better off keeping.
I’m of course referring to Brady Anderson, who years later blasted 50 home runs and finished in the top-10 in MVP voting. The Red Sox sure could have used that one brilliant season from Anderson in 1996, but instead they had to watch it happen for the division rival Baltimore Orioles.
Oh, they also gave up Curt Schilling, who went on to have a Hall of Fame career.
Schilling was a late bloomer who didn’t break out until years later when he had already moved on from Baltimore, but the Red Sox could have reaped the benefits of some of his best seasons if they had patiently waited for him to develop instead of dealing him for a quick fix. Boddicker did a fine job in Boston, but would you rather have him for a few good years or potentially have Schilling for his entire career?
Boston rectified this mistake by bringing Schilling back in 2004 and he ended up winning a pair of World Series rings in a Red Sox uniform. It worked out in the end, but you have to wonder how many more rings this team would have won if they had Schilling in the rotation through his prime years instead of only the tail end of his career.
Next: Bagwell
Jeff Bagwell for Larry Anderson – 1990
This is the trade that comes to mind when Red Sox fans preach caution of giving up prospects for a quick fix.
I’m cheating a bit here, as this trade actually took place as a waiver wire deal at the end of August, but it’s still the same idea. The Red Sox made a mid-season deal to bolster their bullpen by acquiring reliever Larry Anderson, but the ramifications of this decision would haunt them for years to come.
Anderson did a fine job for the Red Sox, posting a 1.23 ERA over 22 innings down the stretch. Unfortunately, that’s all they got from him, as he moved on after that season.
So for essentially one month of having Anderson in the bullpen the Red Sox gave up Bagwell, who became an iconic star for the Houston Astros. In his 15 year career, Bagwell hit .297/.408/.540 with 449 home runs. He won an MVP, a Gold Glove and made four All-Star appearances en route to compiling a resume that should eventually put him in Cooperstown.
Fans are quick to jump on any rumor that could potentially bring a difference maker that can help win this year, but the Bagwell trade offers a cautionary tale of why they should be hesitant to give up top prospects like Yoan Moncada and Andrew Benintendi. You consider it if you’re getting a sure thing that remains controllable beyond this year like Chris Sale, but anything short of a player of that caliber should be a non-starter for any deadline deal conversations involving those young studs.
Next: Trade Possibility: Hanley Ramirez
The reason why? They don’t want to be the team that gives up the next Jeff Bagwell in order to get a Larry Anderson type addition. Not again.