The Red Sox have been strapped for cash for the past couple of years thanks in part to the ridiculous contracts doled out by former general manager Ben Cherington. Rick Porcello's albatross four-year, $82.5 million deal certainly comes to mind.
Adding star slugger JD Martinez on a front-loaded five-year, $110 million deal prior to the 2018 season also didn't help their financial flexibility.
But the Red Sox have a chance to upgrade massively this offseason with Houston Astros star Gerrit Cole slated to hit free agency. If they can clear Martinez and Porcello's contracts, they could sign both him and Jose Abreu ahead of the 2020 season.
Porcello, who will be 31 next year, is slated to come off the books at the end of the season, so all they need to do is resist what little urge they might have to bring him back.
Martinez is a different story. He could opt-out at the end of the season and test free agency heading into his age-32 season, or he could opt into the remaining three years of his deal. If the Red Sox do end up selling at the trade deadline this year, then shipping out Martinez would clear his possible $23.75 million for next year out of the way in a hurry.