The Red Sox have plenty of free agents to deal with this offseason. A risky deadline move could pay dividends in the long run.

Craig Kimbrel is the one of the most dominant closers in recent MLB history; however his contract is expiring at the end of the season. The Red Sox have to weigh in on many contracts coming up this next offseason and in the 2020 offseason.

Fans are certainly aware of the aggressive nature of Dave Dombrowski. The GM has been known to be a buyer, but we rarely ever see Dave trade away big players. In a bold move, the Sox could test the waters for their closer at the deadline.

Option 1:

The Red Sox trade Craig Kimbrel for top prospect(s), major league bat, or major league arm.

The idea here comes from a feat that was pulled off by the rival New York Yankees. They sold their prized closer, Aroldis Chapman, to the Cubs in exchange for Gleyber Torres. In addition, the Yankees were able to resign Chapman in the offseason.

To trade Kimbrel away in the middle of a pennant race would be the ultimate bold move; however the Sox could then use lesser prospects to acquire a closer such as Brad Hand. They would obtain a closer with years of team control, upgrade prospects, and shed future contractual obligations.


  • Acquire top prospect(s)
  • Acquire proven closer with team control
  • Kimbrel may resign in the offseason


  • Kimbrel does not resign with Boston
  • The new Red Sox bullpen falters in the playoffs
  • The acquired prospects don’t pan out

Option 2:

The second option revolves around the Red Sox keeping Kimbrel for the rest of the season and beginning a battle resign him. Lately, the Sox have been notorious for low-balling their pending free agents (see: Jon Lester) and watching them walk out the door. The Red Sox would likely have to deal out a large sum of money similar to that of Kenley Jansen or Chapman to retain their closer.

The Dodgers signed Jansen to a 5 year / $80 million extension.


  • Red Sox maintain solid bullpen
  • Kimbrel remains the closer
  • Sox are set up for playoff push


  • Kimbrel will come at a premium price
  • If he leaves, the Sox will have nothing to show for it (except a possible compensation pick)

Hot Take:

If I am the Red Sox I take the gamble with option one. Joe Kelly has been solid in a set up role and could prove to be valuable as a closer, or remain viable in his current position if the Sox were to obtain a different closer.

The impending return of Tyler Thornburg will allow for flexibility in the bullpen, if Dave Dombrowski were to get creative.

A move of this magnitude is unprecedented in the current state of a playoff race; however success could greatly improve the Red Sox future outlook. An aggressive move without results could ultimately lead to Dombrowski’s demise in Boston.