Red Sox: Mookie Betts trade will have several complications

The Boston Red Sox may be on the verge of trading the most talented player they have ever developed, but several obstacles are in the way.

Newly hired Red Sox Chief Baseball Officer, Chaim Bloom, is presently attending the MLB GM meetings, which are currently underway in Phoenix, Arizona. Executives from every Major League team will be on hand, as well as representatives for many of the sport’s top free agents.

Historically not many major trades or signings will occur during this annual meet-and-greet. Rather all of the aforementioned parties will essentially get a sense of the types of markets that might potentially develop for the transactions they will try to pursue ahead of next month’s Winter Meetings.

For Boston’s new top executive, the most prominent task on his agenda will be to finally have a resolution on Mookie Betts‘ future with the club. Bloom will be meeting with representatives this week for his MVP right fielder, but whatever their actual goal truly is, remains open to interpretation.

The Red Sox will meet with Mookie Betts' representatives this week: https://t.co/ZcfOTq385d
— Chris Cotillo (@ChrisCotillo) November 12, 2019

The Red Sox overall payroll currently sits at $229 million for the 2020 season per Fangraphs.

The front office has said numerous times that getting below the luxury tax (CBT) threshold of $208 million is the ideal goal but not necessarily a mandate. It’s a nice idea, but when other teams have been informed that all of Boston’s starting pitchers are available for trade, as well as a couple of specific outfielders, it certainly seems like a definite mandate.

A recent development that complicates the “mandate” of getting below the CBT, is the fact J.D. Martinez opted into the third year of his contract, which has an average annual value of $22 million.

On his own accord, Betts has publicly maintained since before the start of the 2017 season that he has no intention whatsoever of signing an early extension with his current club. He reiterated those exact same sentiments to the Boston media during clubhouse interviews this past September. It would be a stunning turn of events if suddenly both sides lay down the framework of any such extension following their meeting this week.

While Red Sox will likely gauge the trade market for Mookie Betts this winter, there’s great skepticism any interested team will trade a package of great prospects and pay about $28M for 1 year even for a superstar such as Betts.
— Jon Heyman (@JonHeyman) November 12, 2019

As Jon Heyman points out, trading the 2018 American League MVP could also be a very tall task. With only one year remaining on his deal, only a “win-now” type team would be interested. The Atlanta Braves and Los Angeles Dodgers come to mind as both have assets, and each has fallen just short of a championship the last few years.

If Boston has a high asking price for Betts, inquiring teams might instead pursue the services of infielder Francisco Lindor, who brings far better value with two years of control remaining. As well as four consecutive All-Star appearances, and World Series experience.

The Cleveland Indians have been known to wheel-and-deal. They received a huge haul for trading Trevor Bauer in a blockbuster three-way deal last July with the Cincinnati Reds and San Diego Padres. Not to mention smaller trades with the Tampa Bay Rays and Seattle Mariners.

Another alternative trade to Betts is the 2016 National League MVP, Kris Bryant. Like Lindor, the Chicago third baseman also has two years remaining on his deal. However, this is pending a grievance against the Cubs in regards to his service time being manipulated.

If Bryant wins his case, he would reach free agency a year earlier than currently scheduled. Arbiters will rule on the issue in the coming days and his market will become more clear.

Another scenario would be a one for one swap with the New York Mets. Joel Sherman recently speculated that the Red Sox could send Betts to Queens for Noah Syndergaard.

In 2014, Jon Lester was dealt from Boston to Oakland in a similar trade for Yoenis Cespedes after a contract agreement could not be reached with the longtime ace. Cespedes was parlayed to the Tigers the following winter for Rick Porcello.

Syndergaard is controllable for the next two seasons, however, his projected $9.9 million arbitration price tag is still problematic for the Red Sox in terms of getting below the CBT.

Also problematic is that the burly Mets pitcher has often been a central figure in what has been perceived by many observers as a troublesome clubhouse. As the Jacob deGrom contract negotiations were getting sorted out, Syndergaard was very outspoken against his own organization for not getting a deal done with his Cy Young-winning teammate.

Syndergaard was asked by Mets training staff in April of 2017 to undergo an MRI on his shoulder. He refused that request and then exited his next start with a torn lat muscle.