The last 24 hours of the MLB trade deadline were a flurry of activity. The Boston Red Sox were engaged on a number of fronts as the team tried to improve their roster before the deadline closed. Chief baseball officer Craig Breslow made a couple of moves on Thursday, bringing in reliever Steven Matz and starter Dustin May.

However, the one move that Boston did not make might come back to haunt them. Red Sox beat writer Jen McCaffrey wrote about the team's failed bid to try and acquire Minnesota Twins All-Star starting pitcher Joe Ryan on Thursday after the deadline.

“As the minutes ticked closer to Thursday’s 6 p.m. ET trade deadline, the Boston Red Sox reached out to the Minnesota Twins about coveted starter Joe Ryan,” wrote McCaffrey. “But according to league sources briefed on discussions from the Twins’ side, talks fell apart when the Red Sox were unwilling to offer any of their big-league outfielders or an enticing enough package of their top-tier prospects.

“Jhostynxon Garcia, the Red Sox’s top outfield prospect, was in the mix to be in the deal. But despite Boston’s highly regarded farm system, sources said that the rest of the haul offered was not substantial enough to land Ryan, owner of a 2.82 ERA and whose value is enhanced by being under team control through 2027.”

With staff ace Garrett Crochet in place, Breslow and the Boston brass wanted to add to their starting rotation. May could be an important piece moving forward, but more was clearly needed.

Rumors that the team was chasing higher-end starters like Ryan and the Miami Marlins' Sandy Alcantara flew around more frequently as the deadline approaches. Now the Red Sox need to focus on how to lock in their return to the postseason. Did Breslow do enough, or should he also have pulled the trigger on a deal for Ryan?

Can Red Sox clinch postseason berth after MLB trade deadline moves?

Boston Red Sox chief baseball officer Craig Breslow speaks with the media at the Hilton Anatole during the 2024 MLB Winter Meetings.
Jerome Miron-USA TODAY Sports

While Crochet has certainly held up his end of the bargain, fellow offseason addition Walker Buehler has not. At the moment, he's still in Boston's rotation. Swinging another deal to replace him in the rotation would have likely been the best course of action. Ryan would have been the No. 2 starter in a Red Sox rotation that could have certainly used him come October.

Now though, Boston will move forward with what they have on hand. Crochet and Buehler have two spots. May has a third. Lucas Giolito has returned from Tommy John surgery this season and has shouldered a strong load. Brayan Bello is a homegrown success story.

Will it be enough to get the Red Sox back to the postseason? Or will Breslow regret not trading another piece or two to land Ryan?