Do recent big extensions pressure Red Sox to follow suit?

by Chris Gionta · February 27, 2019

Featured image courtesy of Zimbio.com: (Oct. 17, 2018 – Source: Elsa/Getty Images North America)

In roughly the last 48 hours, there were three very big extensions handed out to excellent players. It began Monday morning when the Yankees announced a 7-year/$70 million extension for CF Aaron Hicks. Then, Ken Rosenthal reported an 8-year/$260 million extension for Rockies 3B Nolan Arenado, who was ranked #3 in MLB Network’s Top 100 Players Right Now. Very shortly after, the Cardinals signed their best pitcher, Miles Mikolas, to a 4-year/$68 million extension. All the deals were relatively different, but they all had one thing in common: these players were under their last year of their contracts.

How does this relate to the Red Sox? Well, the reigning champions have a lot of their top players eligible to leave after 2019, and the reigning MVP, Mookie Betts, eligible to leave after 2020. Chris Sale, Rick Porcello and Xander Bogaerts are all set to be free agents after this year. Perhaps more importantly, J.D. Martinez can opt out after 2019, which is a very likely scenario. He is set to make $62.5 million from 2020-2022, and he would likely make more than that on the open market if he opted out. The odds that all of these players end up on the open market is unlikely, but players might be looking at these recent signings and wondering where their offers are. Everyone now knows how much of a nightmare free agency is, so one would figure that a player would like to get things done sooner rather than later.

It is very rare that a team has five major contributors coming off the books after the same year, then an MVP-caliber player eligible to leave the year after. So, it seems ideal to have at least one of them on a long-term deal by Opening Day of 2019. From there, it comes down to who they want to extend first. Xander Bogaerts, J.D. Martinez, and Jackie Bradley Jr. are all Scott Boras clients, likely meaning that getting as much money as possible is the goal. John Henry has been vocal about signing Chris Sale long-term, and he is probably the best player out of all the players eligible to leave after 2019. But one could argue that Xander Bogaerts is a safer investment, as he is three years younger with less of an injury factor. Then of course, there are Betts and Martinez, who finished 1st and 4th for the AL MVP in 2018.

Either way, I think everybody would sleep a little better at night if the Red Sox extended at least one of Sale, Bogaerts, Martinez, Porcello, Bradley Jr. or Betts before the regular season started. Now is the time to get these things done, so hopefully the activities of the Yankees, Rockies, and Cardinals can inspire the Red Sox to secure their future.