Mandatory Credit: Mark L. Baer-USA TODAY Sports
The Boston Red Sox finished the 2015 season with a disappointing 78-84 record, and another last place finish in the American League East. General manager Ben Cherington has long since departed and President Dave Dombrowski is in position to make some moves to get an expensive–and talented–team back into postseason contention.
The Red Sox should be willing to make whatever moves are necessary to get their fan base invigorated by a winning team. The Red Sox had some good will built up after the 2013 World Championship washed away the nightmare of Bobby Valentine and loss of curse-busting general manager Theo Epstein, but consecutive last place finishes have left a region used to their baseball team being relevant in October disappointed.
While the winter meetings are still a month away, the buzz is building as the World Series has now ended. While there are a number of free agents who are likely going to be of interest to the Red Sox and their deep pockets, Dombrowski in his career has often preferred to wheel and deal and make trades to build talent.
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The Red Sox minor league system is stacked at all levels and the new management team in town has no attachment to any players on the roster. Whether it is young position players such as Yoan Moncada, Manuel Margot, Andrew Benintendi, and Sam Travis or ready to start pitchers like Brian Johnson, Henry Owens, Matt Barnes, and Pat Light the Red Sox are in position to offer trade partners exactly what they are looking for to restock their team.
Since taking over, Dombrowski and his assistants have been in evaluation mode determining what prospects are worth keeping and who to deal for established veterans In addition, he and his team has to be in evaluation mode of the other teams to determine which players to target.
Here are five realistic targets the Boston Red Sox should be targeting to obtain via trade and upgrade the roster this winter. While they may not be able to get all five, at least one of these targets could help bump the Red Sox back up the standings in 2016.
Next: A Young Ace
Stephen Strasburg, SP – Washington Nationals
Mandatory Credit: Dale Zanine-USA TODAY Sports
The Boston Red Sox are in the market to add a frontline starting pitchers. It is no secret after the Red Sox let ace Jon Lester leave without a serious offer in the offseason and the front office rolled out a rotation of number three starters which predictably did not work out as well as former general manager Ben Cherington envisioned.
With Dave Dombrowski historically more inclined to deal for an ace rather than sign one of the available pitchers in free agency, there are some big names who may be available for a significant cost if a team deep with prime prospects (like the Red Sox). These three targets are all young, not too expensive yet and may be on the market in the offseason.
Stephen Strasburg is on a Washington Nationals team which is loaded with talent and with a couple of starters free agents, they have a decision to make if they re-sign Jordan Zimmerman and Doug Fister and deal Strasburg who is entering his final season under arbitration and would be a free agent after next season.
Strasburg may be available simply because he has not stayed healthy. He is just 27 years old and a team not afraid of the cost with a team ERA which was 25th in MLB should be interested. Strasburg’s price may not be as high as other pitchers under team control due to his pending free agency.
Next: Yet Another Ace
Matt Harvey, SP – New York Mets
Mandatory Credit: Jeff Curry-USA TODAY Sports
On one hand, the Mets would appear to have plans to deal Matt Harvey. He is the ace of a young staff which is in the World Series and could be the centerpiece of their rotation for years to come. However, the Mets have had a minor issue with Harvey’s innings limit and dealing with agent Scott Boras.
The Mets are also facing the prospect of numerous players hitting free agency and not wanting to allocate the money or want to offer long-term deals Daniel Murphy, Tyler Clippard, or Yoenis Cespedes. Where the Mets are deep is in the starting rotation and trading a pitcher for a package of position players could help the Mets compete without breaking the bank.
The question for Boston is the price tag to bring the Connecticut native back to New England. The Mets are not giving up Harvey for a discount rate and they are going to want a player who can contribute immediately in order to sell the trade to their fans. A player such as Mookie Betts or Xander Bogaerts may have to be part of the deal.
With the previous Red Sox front office adamant about not trading Bogaerts or Betts, it is unknown if Dombrowski would be willing to deal one of the exciting young prospects. Both are proven major league talents and their cost is low. If the Red Sox are willing to move one of these players, they had better get a top talent like Harvey in return.
Next: Even More Starting Pitching
Sonny Gray, SP – Oakland A’s
Mandatory Credit: Ed Szczepanski-USA TODAY Sports
A final starting pitching target the Red Sox should be trying to trade for is Oakland A’s young ace Sonny Gray. Gray has won 14 games in each of the past two seasons and would be just 26 years old in 2016. Gray is one of the top pitchers in baseball and his talent, age, and contract make him a prime target for the Red Sox.
The A’s are rebuilding and need help all over the roster. General manager Billy Beane needs to rebuild the entire team and obtain as much talent as possible rather than muddling along as he has with Oakland the past few seasons. The roster lacks star power in the infield and outfield, has little power, and need to fill holes in the rotation and bullpen.
The only trade chip they have is Gray. While Gray is their only legitimate star, Oakland may be willing to let him go for a haul of prospects. Few teams can offer the depth of talent that the Red Sox can to entice the A’s. It is not going to come cheap for the Red Sox to acquire Gray as Beane is going to have to be overwhelmed.
No one knows what Beane is going to be looking for if he decides to deal Gray. Will he want a low-level prospect such as Manuel Margot along with a starting pitcher ready to contribute like Henry Owens? A catcher like Blake Swihart would probably be attractive the A’s as well. A Mookie Betts, Yoan Moncada, or Xander Bogaerts would probably be too enticing for Beane to pass up.
Next: Bullpen Help
Craig Kimbrel, CL – San Diego Padres
Mandatory Credit: Jake Roth-USA TODAY Sports
Craig Kimbrel was a much discussed trade target at the trading deadline as the former Atlanta Braves closer seemed wasted in San Diego. With the Padres coming off a bad season in 2015 and with his expensive contract, Kimbrel seems destined to be back on the trade market.
Kimbrel has been otherworldly in his career as a closer. Whatever statistic you want to pull out to grade Kimbrel be it ERA, ERA+, WHIP, FIP, or just plain old saves, he is a premier closer and with Mariano Rivera retired, he is simply the best closer in baseball.
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The Red Sox–as anyone who watched the give away games with their motley crew of relief pitchers is aware–are in need of bullpen help. Without Koji Uehara healthy, the Red Sox late innings bullpen crumbled in 2015.
While the Red Sox will be paying Uehara close to $9 million in 2016, if he is the eighth inning set-up man for a team contending for the playoffs no one will complain about the cost. Dave Dombrowski may have to flip Uehara for a prospect to recoup the prospects it would cost for Kimbrel.
Kimbrel is under contract for 2016 for $13 million and has a team option for 2017 at the same price tag. He will be 28 in 2016 and remains the premier closer in baseball. As such, the price will not be cheap. However, with a need for bullpen help, it makes sense for the Red Sox to target the best available while they have the deep farm system to entice the Padres to trade him.
Next: A Powerful Bat at Needed Position
Chris Carter, 1B – Houston Astros
Mandatory Credit: Troy Taormina-USA TODAY Sports
The Red Sox are saying all the right things about Hanley Ramirez and his possible move to first base in the spring. However, all of those comments do not mean much if he is not on the team. It may look impossible to move Ramirez with all the money owed to him on his contract, but Dave Dombrowski has a reputation for being able to make any bad contract go away.
An interesting option to add power at first base is Houston Astros first baseman Chris Carter. Carter is arbitration eligible and seems to be that power hitter who is the proverbial late bloomer. The Red Sox struck gold 13 years ago taking a shot on a late bloomer named David Ortiz. While no one expects Carter to become a future Hall-of-Fame player, he does have intriguing power.
Next: Red Sox Should Target Free Agent SP John Lackey
Carter will be 29 years old in 2015 and the massive (six-foot-four and 250 pounds) slugger is arbitration eligible. A tease in Oakland for so many years, he has hit 29, 37, and 24 home runs in Houston the past three seasons. The knock on Carter is the strikeouts and batting average. For a team that has focused on power and on-base percentage, Carter could be a target in Boston.
Carter would give the Red Sox some serious right-handed power if slotted behind Ortiz in the lineup. An inexpensive and potential replacement for Ortiz at designated hitter, Carter could be peppering the Green Monster and launching balls to the Mass Pike without costing much in return. Some modest prospects could pry Carter from Houston.

