Opening Day usually signals the end of all offseason business around baseball, and it’s often when teams table contract extension talks with players they’re looking to lock up. But if the Red Sox have their way, they’ll be busy in the coming hours and days.
Weeks after locking up young starter Brayan Bello on a six-year, $55 million extension, the Red Sox are still trying to get similar deals done. And according to team president/CEO Sam Kennedy, there’s a chance more action happens before the season begins at 10:10 p.m. ET on Thursday night — or shortly thereafter.
“I’m hopeful,” Kennedy said on the latest episode of MassLive’s Fenway Rundown podcast. “What I’ll say on that is (chief baseball officer Craig Breslow) and his team are engaged and have been engaged in a lot of discussions — internal discussions, external discussions, free agent conversations. Internally, the formula of signing and extending your known entities, your known talent, is really important and there’s lots of those discussions that have gone on. That’s all I can say publicly, but I think I’m hopeful that we’ll be in a position to get something across the line here soon. We may not, but it’d be great to get multiple deals across the line. There’s a lot of conversations going on.”
Pushed on if something was close, Kennedy — who recorded the podcast at 5 p.m. ET on Wednesday afternoon — said the situation was fluid.
“I don’t want to give you anything that is factually incorrect,” he said, ”but there have been multiple conversations going on up until this point. I don’t know exactly where Brez stands with each and every one of those, but I am hopeful that something may get over the line either prior to Opening Day or shortly thereafter. I’m an optimist. I’m hopeful. But certainly can’t guarantee anything. So we’ll see what the next 24 hours brings.”
The Red Sox entered the winter aiming to aggressively pursue extensions with young players before Opening Day. The Bello deal, which was finalized March 9 and celebrated during the club’s subsequent trip to the Dominican Republic, marked an important step as it was just the second extension the Red Sox had given to a pre-arbitration player since 2011. Club officials have remained hopeful throughout spring training that Bello would not be the only young player to put pen to paper by the end of camp.
Boston’s top extension target is first baseman Triston Casas but it would be a massive surprise if he were to sign anytime soon. In a conversation with The Boston Globe’s Alex Speier earlier this week, Casas said the Red Sox made him an offer a few weeks ago that his agency deemed to be too low to accept and that he was likely to pick up negotiations after the season. A baseball source confirmed to MassLive that an offer was made that was not in the ballpark of what Casas is looking for.
If the Red Sox have made progress with an extension candidate, it’s unclear who that player is. Right-handers Tanner Houck and Kutter Crawford don’t appear to be close anything. Houck has acknowledged throughout the spring that talks have taken place but told Speier that the sides could not reach an agreement. Crawford told The Globe’s Pete Abraham that he had not been approached.
Other theoretical extension candidates include infielder Vaughn Grissom, outfielders Ceddanne Rafaela, Wilyer Abreu and Jarren Duran and potentially even righty Josh Winckowski, though it’s unknown if any of those players have been approached. The Red Sox could also try to work out a long-term deal with pending free agent Nick Pivetta.
There are recent precedents for the team getting deals done after playing its first game of the season. In 2019, Xander Bogaerts’ extension was announced before the fifth game of the season. Three years later, Garrett Whitlock’s deal broke before the third game of the year in New York.
The Red Sox are hoping history repeats itself.
“Once you know that you have someone who’s capable of success in Boston, I think it’s important that you ferociously go after them to try and keep them here,” Kennedy said.
