10 Blockbuster Deals Red Sox GM Should Be Proposing

Evan Brunell@evanbrunellFeatured ColumnistJuly 15, 2014

10 Blockbuster Deals Red Sox GM Should Be Proposing

0 of 10

    The last blockbuster deal Boston pulled off led to a World Series the next year. Can the Red Sox do it again?
    The last blockbuster deal Boston pulled off led to a World Series the next year. Can the Red Sox do it again?Damian Dovarganes/Associated Press

    On August 25, 2012, the Boston Red Sox stunned the baseball world by shipping out players Josh Beckett, Carl Crawford, Adrian Gonzalez and Nick Punto to the Los Angeles Dodgers in a massive salary-clearing move that rebooted the Red Sox franchise and led to a World Series the next season.

    The deal continues to bear fruit for the Red Sox, even as three of the five players sent back to Boston are no longer with the team. It was all about the two pitching prospects Los Angeles sent: Rubby de la Rosa and Allen Webster. De La Rosa is now a member of the Red Sox rotation and has a 2.89 ERA in six starts, while Webster has a 3.05 ERA in 20 games for the Triple-A Pawtucket Red Sox.

    What blockbuster deals could GM Ben Cherington pursue to put another World Series ring on his finger?

    At 43-52 entering the All-Star break, Cherington is in an interesting position. He could go for it in a wide-open AL East race. While the club is 9.5 games out of first place, the team has started to play better recently with more energy and having won four of the last five games.

    Or Boston could throw in the towel and focus all its energies on the future, dealing away would-be free agents in an attempt to put the Red Sox on strong footing to contend in 2015 and beyond.

    With quality veterans and a farm system teeming with prospects, the chips are there for the Red Sox to make some blockbuster trades. Let's look at some possibilities.

    Note: These proposals are more concerned with the logic from the Red Sox's side and what the acquisition cost would be in the trades and less so with the logic from the opposing team's side in trading suggested players. We're discussing what deals the Red Sox GM should be proposing, not what necessarily gets executed.

10. Koji Time in Detroit

1 of 10

    Uehara would give the Tigers the weapon they need in the bullpen.
    Uehara would give the Tigers the weapon they need in the bullpen.Charles Krupa/Associated Press

    Boston Red Sox trade: closer Koji Uehara; shortstop Stephen Drew

    Detroit Tigers trade: pitcher Jonathon Crawford; infielder Steven Fuentes

    If the Red Sox choose the rebuilding route, what use is it to hold on to a 39-year-old closer who will become a free agent after the season?

    The Detroit Tigers are in desperate need of shoring up their bullpen with Joe Nathan a liability. The former All-Star closer has a 5.61 ERA on the season and has blown five of 24 save opportunities. Adding Uehara would give Detroit the ability to lock down games. Further, Uehara is battle-tested in the playoffs, as his 2013 ALCS MVP award can attest.

    Detroit also needs help at shortstop, as the team has struggled to find a solution ever since Jose Iglesias went down with a season-ending injury before the year even got started. While Drew hasn't hit well since re-signing with Boston, the 31-year-old is showing some signs of life with a .167/.306/.433 line in 10 July games to date.

    If the Red Sox ate a significant portion of Drew's contract, the Tigers would jump at the opportunity to add a steady veteran glove. If the offense never comes around...well, it's not like Detroit is getting production out of the position at the moment, anyway.

    In return for giving up Uehara and Drew, the Red Sox would pick up 22-year-old starting pitcher prospect Jonathan Crawford who was selected in the first round of the 2013 draft. He projects as a mid-rotation starter and could move fast through the farm. Steven Fuentes, meanwhile is a raw, toolsy infielder who is far away but boasts intriguing upside.

9. Lackey to St. Louis

2 of 10

    Grichuk could push for the starting center field job.
    Grichuk could push for the starting center field job.Jeff Roberson/Associated Press

    Boston Red Sox trade: pitcher John Lackey; outfielder Jonny Gomes

    St. Louis Cardinals trade: outfielder Stephen Piscotty; outfielder Randal Grichuk

    As the Cardinals scratch and claw their way to another postseason appearance, they could sure use another pitcher in the rotation.

    Enter John Lackey, who has enjoyed a career renaissance after undergoing Tommy John surgery. The 35-year-old would fit in well with the Cardinals behind Adam Wainwright and give the team a weapon as it attempts to fend off the Milwaukee Brewers, Cincinnati Reds and Pittsburgh Pirates in a competitive NL Central division. 

    It's not just a one-year rental, either.

    The Red Sox hold a club option on Lackey for the major league minimum salary next season. When Lackey originally signed his five-year contract with Boston, language was built in the deal to give Boston this option if Lackey missed significant time with an elbow injury...which he did when he underwent Tommy John surgery. The extra year at so little money would be extremely valuable to the Cardinals.

    Gomes, meanwhile, would give the Cardinals a weapon off the bench to attack left-handed hitting.

    From Boston's side of things, it would gain two outfielders in Stephen Piscotty and Grichuk. Piscotty is one of St. Louis' top prospects who could take over for Shane Victorino in right field in 2015. He could potentially hit .300 with over 30 doubles and 15 home runs, as Baseball Prospectus' Jason Parks writes (subscription required), which is All-Star production.

    Grichuk, meanwhile, has latent power in his bat and can man center field but his best position is most likely right field. He does have a chance to develop into a starting outfielder, but he would be valuable as a cost-controlled outfielder who can come off the bench with a bit of sock in the bat.

8. Bundy to Boston

3 of 10

    Bundy could fill Baltimore with regret for years to come if he was dealt to Boston.
    Bundy could fill Baltimore with regret for years to come if he was dealt to Boston.USA TODAY Sports

    Boston Red Sox trade: pitcher John Lackey; reliever Koji Uehara; utility man Brock Holt

    Baltimore Orioles trade: pitcher Dylan Bundy; first baseman Christian Walker; pitcher Stephen Tarpley

    The Baltimore Orioles are built to win now. While there's a window open in the AL East with the Red Sox's slide into last place, the Tampa Bay Rays' confounding ineptitude and a vulnerable New York Yankees team, the O's can't afford to whiff on the opportunity that has been presented to them.

    That's why Baltimore could trade prized pitching prospect Dylan Bundy. And that's not so far-fetched to consider, given GM Dan Duquette did not rule out moving the youngster when the Houston Astros approached him about a potential deal for Bundy, as the Astros' leaked database reveals, per Barry Petchesky of Deadspin.

    Currently rehabbing from Tommy John surgery, Bundy could be Boston's next aceas soon as 2015if he can return fully healthy. That's the kind of upside that Bundy has.

    Meanwhile, Lackey would give the Orioles a tested postseason starter who has proven he can hang in the AL East. Add in Lackey's 2015 salary at the league minimum, and the deal starts making more and more sense for Baltimore.

    Uehara would bring instant legitimacy to the Orioles' bullpen.

    Holt, meanwhile, would plug Baltimore's hole at second base. While losing someone of Holt's intensity and versatility would be a blow to the Red Sox, the club has the depth to withstand moving Holt.

    Further, clearing the 24-year-old out at this stage would be selling high; long term, Holt isn't expected to be much more than a backup infielder. Of course, it's always possible that Holt has developed and is now the real deal, so there's risk here.

    But again...Dylan Bundy.

    Prospects Christian Walker and pitcher Stephen Tarpley round out the deal for Boston, giving the team two intriguing prospects to gamble on.

7. A New Shortstop in Boston

4 of 10

    Andrus would bring a slick glove to Boston.
    Andrus would bring a slick glove to Boston.USA TODAY Sports

    Boston Red Sox trade: utility man Mookie Betts; pitcher Henry Owens; catcher Christian Vazquez; second baseman Sean Coyle

    Texas Rangers trade: shortstop Elvis Andrus; outfielder Alex Rios

    The Rangers have several intriguing infield prospects who would enable the club to move Andrus, who is signed through 2022 on a eight-year deal with a total value of $118 million. 

    Andrus would plug the shortstop carousel that has bedeviled Boston since shortstop Nomar Garciaparra was traded midway through the 2004 season.

    While his offense has fallen this year with a line of .265/.313/.338, he hit .286/.349/.378 in 2012 and may have more potential in the bat. It feels like the Venezuelan is rather old due to having been in the league for quite some time, but he is just 25, making the price for Andrus easier to swallow.

    Further, Rios would plug Boston's outfield hole in a deal structured to try to get Boston back into the division race. Even if the team fails in that pursuit, the Red Sox would have an affordable, $13.5 million club option on Rios for 2015 they would exercise. That would give the Red Sox more outfield depth, and Rios could even serve as additional trade bait.

    For the Rangers, giving up Andrus would command a hefty price, and they would receive just that in return. Betts could fill many roles for Texas and would give the club a dynamic player, while Owens would help Texas rebuild its starting pitching depth.

    Vazquez would be a big addition for the Rangers, who lack options behind the plate; his defense and pitch-calling would be an asset to a rotation that can get Texas to the playoffs when healthy. Lastly, Coyle would give the Rangers yet another quality infield prospect that could be moved in a separate deal.

    Another version of this trade could see the removal of Betts from the deal given the Rangers’ depth in infield prospects. Replacing Betts would likely be a young pitcher, such as Rubby De La Rosa or Allen Webster. Any deal for Andrus would have to include major league-ready players going to Texas, as the team fully expects to contend once again in 2015.

6. Posey Arrives in Boston

5 of 10

    Posey would quickly become a fan favorite in Boston.
    Posey would quickly become a fan favorite in Boston.USA TODAY Sports

    Boston Red Sox tradepitcher Rubby De La Rosa; utility man Mookie Betts; pitcher Henry Owens; catcher Blake Swihart

    San Francisco Giants trade: catcher Buster Posey; pitcher Chase Johnson

    Buster Posey is a popular man in San Francisco, so it's very difficult to see San Francisco entertaining offers for the All-Star backstop, let alone dealing the 2012 NL MVP.

    That said, the proposed package to acquire Posey detailed above would certainly grab GM Brian Sabean's attention. The club is set to lose third baseman Pablo Sandoval to free agency and has a concerning lack of depth and youth on the team. In one fell swoop, the Giants would address that with Mookie Betts, who could be Sandoval's replacement at third.

    De La Rosa would provide an immediate injection of quality into the Giants rotation. The 26-year-old would immediately boast the highest ceiling of any pitching prospect in the San Francisco system. Owens, who should debut at some point in 2015, would also give the Giants another arm, helping to turn the team into contenders and addressing the lack of pitching upside in the farm.

    Lastly, Blake Swihart is one of the best catching prospects in the game and could feasibly debut as early as 2015. While the deal would likely doom San Francisco's chances of making the playoffs in 2014, the Giants would be a very dangerous team again in 2015 with a strong, youthful core.

    The motivation from Boston's end is pretty simple. It's Buster Posey, who has a career line of .302/.370/.476 and would serve as Boston's catcher for years to come. To help save wear and tear on the 27-year-old, Posey could also serve as designated hitter (DH) and play first base, which would have the added benefit of getting catcher Christian Vazquez's defense onto the field.

    Chase Johnson rounds out the deal going Boston’s way, an intriguing starting pitching prospect who likely will end up in the bullpen.

5. Lester Goes West

6 of 10

    Walker would give the Red Sox another impressive young arm.
    Walker would give the Red Sox another impressive young arm.Bob Levey/Getty Images

    Boston Red Sox trade: pitcher Jon Lester; pitcher John Lackey; third baseman Will Middlebrooks

    Seattle Mariners trade: pitcher Taijuan Walker; first baseman Jesus Montero; outfielder Gabriel Guerrero

    If the Red Sox are going to retool for 2015, why not go full bore?

    In this deal, the Red Sox get rid of two-fifths of their rotation, sending Jon Lester home to Washington while also adding John Lackey. The Mariners would suddenly boast one of the best pitching staffs in baseball, if not the best. It would position the Mariners to keep pace with the Athletics' vaunted rotation and give Seattle a notable edge over the Los Angeles Angels.

    Lester could potentially depart as a free agent after the season, but Lackey is tied to the team for 2015, further enhancing the value of the deal for Seattle.

    In return, the Red Sox would get prized pitching prospect Taijuan Walker, who would become part of the next vaunted Red Sox rotation. Walker missed time earlier this season with a shoulder injury, but he has already returned to the major leagues, making two starts and counting.

    The 21-year-old has immense potential to the point you could argue that even with the type of return Seattle is getting in this deal, the Mariners would still not pull the trigger.

    Imagine if GM Jack Zduriencik did make that decision, however. A Red Sox 2015 rotation of Clay Buchholz, Taijuan Walker, Rubby De La Rosa, Brandon Workman and Allen Webster with Henry Owens and Matt Barnes at the ready mark down at the farm is an enviable and youthful rotation.

    The Sox would also receive Jesus Montero, a former heralded Yankees prospect swapped for Michael Pineda prior to the 2013 season. Montero has essentially lost all role with the M's and can't be counted on to do much in Boston. Nonetheless, he is just 24 and perhaps a change of scenery could revitalize Montero. It's worth a chance, anyways.

    In addition to Lester and Lackey, Seattle would also receive power-hitting third baseman Will Middlebrooks, who wouldn’t have much of a role on the 2014 club, but he could be a threat off the bench.

    The Mariners really need a right-handed power bat, and Middlebrooks could pay big dividends on that front. Next season, Middlebrooks could become the club’s first baseman, unless Seattle wanted to keep Morrison at first. That could result in moving Middlebrooks to left field.

    The 25-year-old plays a position in more demand than Montero at first base, and at this stage, Middlebrooks is the more thought-of player between the two.

    Guerrero is a high-risk outfield prospect who could be an All Star or could never sniff the majors.

4. A Star in Boston

7 of 10

    Chicago's hitting depth could make Castro expendable.
    Chicago's hitting depth could make Castro expendable.Brian Kersey/Getty Images

    Boston Red Sox trade: pitcher Henry Owens; pitcher Allen Webster; catcher Christian Vazquez

    Chicago Cubs trade: shortstop Starlin Castro

    The Cubs are deep in hitting prospects, but they desperately need high-flight pitching.

    Chicago can address that problem by trading away incumbent shortstop Starlin Castro, who is rebounding from an off year in 2012 and who now looks to be on the upswing again. Just 24, the shortstop has already been an All-Star three times, including in 2014.

    The Red Sox would certainly live with Castro's average defense at shortstop if it meant getting a bat with such potential in it. While the Dominican struggles with plate discipline, he is making advances in that category. Castro has 25 walks on the season, which is just 11 walks away from his previous career high. As he continues to mature, the walks should rise.

    If the Red Sox determine Castro's future is not at short, the value he brings with the bat will still play at another position, such as third base.

    As stated, the Cubs need pitching. Acquiring Boston's top pitching prospect, plus hard thrower Allen Webster, will go a long way toward solving Chicago's pitching depth. Webster would slot in the rotation immediately and could be an established member by the time the Cubs are ready to contend.

    While Owens is a bit further off, his arrival time meshes with that of the best hitting prospects the Cubs have and could eventually pair with Webster in the middle of the rotation. The ceilings of the two pitchers are as front-line pitchers, so there's a lot of upside for Chicago to capitalize on.

    Vazquez rounds out the deal and could immediately supplant Welington Castillo as Chicago's catcher.

3. Another Blockbuster with the Dodgers

8 of 10

    Pederson's power would be welcome in Boston's outfield.
    Pederson's power would be welcome in Boston's outfield.Christian Petersen/Getty Images

    Boston Red Sox trade: pitcher Jon Lester; third baseman Will Middlebrooks; reliever Craig Breslow

    Los Angeles Dodgers trade: outfielder Joc Pederson; pitcher Zach Lee; pitcher Paco Rodriguez

    The Dodgers have their sights set on the World Series in 2014, and in one fell swoop they could make a massive advance toward that goal, while also keeping the future in mind.

    Lester would join an unconscionable rotation, forming a devastating quintet with Clayton Kershaw, Zack Greinke, Josh Beckett and Hyun-Jin Ryu. Four out of the five starting pitchers would have ERAs under 3.00, and Ryu's FIP is also under 3.00. No team would have any interest in facing Los Angeles in October with that kind of rotation.

    The Dodgers can certainly afford to re-sign Lester once the left-hander becomes a free agent, and having Lester pitch half the season in Dodger blue could give Los Angeles a leg up on bringing Lester back, especially if it makes a deep playoff run. The deal would also reunite Lester with buddy Beckett.

    Middlebrooks could easily take over immediately at third base or share in a platoon with Juan Uribe. In 2015, he would serve as the starting third baseman and replace the power potential that would be lost in the Dodgers' shedding of Pederson. Meanwhile, Breslow would help round out Los Angeles' bullpen; while Breslow has struggled this year, he still brings a lot to the table.

    Pederson would be the key to this deal for Boston, as the Red Sox would add an outfielder with power who is capable of playing center field or who could slide over to right field and displace Shane Victorino.

    The Red Sox consider right field a second center field, so having Pederson in right field would make full use of his defensive capabilities. He boasts five tools and could end up as the long-term No. 2 or No. 3 hitter in the lineup, forming quite a dynamic duo with Boston's own star prospect, Xander Bogaerts.

    Lee would help keep Boston's pitching-depth impact. The former first-round pick doesn't have a high ceiling, but he can function in the middle of the rotation. If the 22-year-old isn't a fit with Boston, there are plenty of other teams that would be happy to trade for Lee.

    Rodriguez could supplant Breslow in the bullpen and would give Boston a left-handed flamethrower, which would ease the sting of a possible Andrew Miller departure in free agency.

2. Tulowitzki Joins Red Sox

9 of 10

    Tulowitzki could halt Boston's shortstop carousel for a long time.
    Tulowitzki could halt Boston's shortstop carousel for a long time.Justin Edmonds/Getty Images

    Boston Red Sox trade: utility man Mookie Betts; pitcher Henry Owens; pitcher Allen Webster; shortstop Deven Marrero; second baseman Sean Coyle

    Colorado Rockies trade: shortstop Troy Tulowitzki; outfielder Drew Stubbs

    Well, this is one way to shake up the fortunes of two teams.

    On the Red Sox's side, the addition of Troy Tulowitzki would immediately give the club an injection of power it needs for the next contending team. This power would come from shortstop, a position where defense is generally prioritized over offense. Having such a talented hitter at short would represent tremendous value for Boston.

    Tulowitzki is in the midst of a season that may garner him the NL MVP award when the season is over, as he's hitting .345/.435/.613 through the first half of the season. The .345 batting average and .435 on-base percentage lead the majors, while his .613 slugging percentage tops the NL leaderboard.

    If the Red Sox want to try to make a go of contention the rest of the way in 2014, the team can't do much better than adding Tulowitzki. This iteration of a deal also includes outfielder Drew Stubbs, who can play all three positions ably and who would provide another dose of power.

    It still remains to be seen if Stubbs' resurgence this year is fueled by Coors Field or not. It sure seems so, given his 1.081 OPS at home in 140 plate appearances as opposed to a paltry .582 on the road. Stubbs is no solution on his own, but throwing the 29-year-old into the outfield rotation mixture can only lead to good outcomes.

    As for Colorado's return, the club would get a haul that can enable it to cobble together a strong rotation for 2015 and begin the road to contention. Colorado has difficulty luring pitchers to pitch in Coors Field, but those who are traded or drafted don't have much say.

    By trading for Allen Webster, Colorado will be acquiring someone with a big fastball that can withstand the rigors of high altitude, while adding a player of Owens' caliber to its prospects list gives Colorado a real chance to do some damage on the pitching side. Ending the 2015 season with a rotation of rookies Jonathan Gray, Eddie Butler, Webster and Owens would put Colorado on the path to contention.

    Meanwhile, Betts is versatile enough that he could feasibly fill the hole Tulowitzki's departure would cause. Even if Betts ends up better leveraged at second base or the outfield, there's no shortage of spots where he can perform his duties. 

    If Betts is best-used elsewhere, the Rockies would get a lot of use out of Deven Marrero, also a piece of this trade concept.

    Marrero, a first-round pick by Boston in 2012, is a defense-first shortstop, but he has had a coming-out party with his bat in 2014. While he'll never make an All-Star Game based on the strength of his bat, his combined line of .296/.369/.431 between Double-A and Triple-A offer reason for optimism.

    Finally, Coyle rounds out the deal. A diminutive second baseman, all Coyle does is hit and could be Colorado's second baseman in short order. Currently hitting .336 in Double-A, Coyle has been an unheralded prospect prior to 2014 since being plucked in the third round of the 2010 draft. He's going to start appearing on lists of top-10 prospects for the Red Sox after the season.

    All in all, the Rockies haul for Tulowitzki could be a no-brainer. They could have an All-Star center fielder in Betts, a slick shortstop in Marrero, another Jose Altuve at second base (minus the stolen bases) in Coyle and two mid-rotation starters.

    That's not a bad haul.

    Meanwhile, Boston will be more than pleased to employ Tulowitzki for the next six seasons.

1. Giancarlo Stanton Packs His Bags

10 of 10

    Stanton would find the Green Monster to his liking.
    Stanton would find the Green Monster to his liking.Ralph Freso/Getty Images

    Boston Red Sox trade: utility man Mookie Betts; pitcher Henry Owens; pitcher Allen Webster; third baseman Will Middlebrooks; pitcher Simon Mercedes

    Miami Marlins trade: outfielder Giancarlo Stanton; reliever Colby Suggs

    Since it's the Miami Marlins, trade rumors have always flown fast and furious surrounding noted slugger Giancarlo Stanton. Every year, Stanton marches closer and closer to free agency and a massive contract. Now that he's two years away from free agency, it gets more realistic by the day that Stanton eventually gets traded. Maybe Stanton signs a deal to remain with the Marlins.

    But if the Marlins are substantially enticed by a trade package, it does not make fiscal sense for the them to turn down such a deal. We can bemoan Marlins owner Jeffrey Loria may be tightfisted all we want, but the facts on the ground remain that Miami simply does not spend money unless fans start flocking to the yard (hint: they haven't); that won't change.

    Betts, Owens and Webster have been pretty consistent members of this series of trade proposals. The players have already had their strengths and weaknesses discussed elsewhere.

    These players represent the upper echelon of Boston's top prospects lists and are of such substantial quality that they can fetch big pieces in return. Boston's minor league system boasts such strength that even clearing these players out would not raze the farm. Besides, Stanton is 24 years of ageit's not like the prospects are being cleared out for players over age 30.

    Middlebrooks has previously been linked to Miami before, as CBS Sports' Jon Heyman recollects. It's easy to see why Miami likes the third baseman. Middlebrooks boasts raw power potential that could one day result in 30-plus home run production. He has plate discipline and consistency strugges, but at 25 years of age, he still has time to figure it out.

    Throughout the Marlins' trade history, the team tends to like acquiring raw pitchers with high upside that are also high risk, in the hopes they can win the lottery. Mercedes' inclusion furthers that trend, as the 22-year-old has a "live arm," according to a Sox Prospects scouting report. Still raw, Mercedes is pitching at Class A Advanced Salem this season.

    In addition to Stanton, the Red Sox would pick up reliever Colby Suggs. Boston lacks high-upside relievers and has shown a proclivity toward trading for them in the past (see: Andrew Bailey, Joel Hanrahan, Mark Melancon). With several members of the current bullpen set to hit free agency, the Red Sox need depth there.

    Getting a haul of Betts, Owens, Webster, Middlebrooks and Mercedes certainly qualifies as being substantial, although it may not be enough to get Stanton at this trade deadline. This offseason? Next trade deadline? This deal would absolutely be taken seriously, if no players involved suffer significant setbacksalthough Mercedes would likely be subbed out for a younger, rawer player in a year.

    At this stage, with the Marlins in quasi-contention and in no hurry to deal Stanton in the hopes a contract extension can be worked out, Miami would not be doing its job if the team did not require the inclusion of Red Sox stud prospect Xander Bogaerts. There is zero chance of this happening, as Bogaerts could one day soon rival Stanton's total production.

    It may take another year yet, but Red Sox GM Ben Cherington needs to make sure he stays in the hunt for Stanton in case a deal can come together that can land the slugger in Boston.

    Note: The Red Sox have been linked to Cole Hamels in trade talks, with The Boston Globe's Nick Cafardo reporting that the team watched a game of the left-hander's last week. There are no blockbuster deals proposed with Hamels in this article because right now, Boston needs to be focused on re-signing Jon Lester.

    By retaining Lester, Boston can direct what resources it has toward obtaining another impact player and coming out a net positive rather than letting Lester walk and using said resources to acquire Hamels.