Why Red Sox must sign Jordan Montgomery amid disappointing offseason

The Red Sox need to sign Jordan Montgomery.

The Boston Red Sox haven’t enjoyed much success in recent years, and this free agency period has fans shaking their heads. The American League East is arguably the most competitive division in baseball, with the Baltimore Orioles and New York Yankees both getting better this winter. The Red Sox? Well, they’ve barely done anything.

The organization traded Chris Sale to the Atlanta Braves and sent Alex Verdugo to the Yankees. They acquired power-hitting outfielder Tyler O’Neill from the St. Louis Cardinals in a trade while signing Lucas Giolito in free agency and getting young infielder Vaughn Grissom in the Sale deal. That’s essentially it.

The Red Sox clearly need pitching. Giolito isn’t exactly consistent and had a rather terrible 2023 season. James Paxton signed with the Los Angeles Dodgers and he was basically their ace at this point after Sale left. Garrett Whitlock, Brayan Bello, Tanner Houck, and Kutter Crawford are the other arms in their rotation.

It’s time for Boston to go out and sign Jordan Montgomery, the best starter left on the open market.

Why Red Sox must sign Jordan Montgomery

Montgomery moved around quite a bit last year but ended up with the Texas Rangers in the second half where he helped them win a World Series. In 32 starts between stints with the Cardinals and the Rangers, the left-hander went 10-11 with a 3.20 ERA, striking out 166 in 188.2 innings while walking just 48. Every fifth day, Montgomery was a workhorse for both ball clubs.

The former Yankee has been garnering a ton of interest on the open market, with the Red Sox, Angels, Giants, and Phillies among the teams eyeing Montgomery, while Texas is very much in the mix for him, too. But for the Red Sox, he must be a priority. Although Montgomery has never been the ace of a staff, he could develop into just that for Alex Cora because let’s be honest, they don’t exactly have a No. 1 option, anyway.

The veteran has seven years of experience and owns a career 3.68 ERA. With Texas, he compiled a 2.79 ERA in 11 regular season starts and also dominated in the postseason. Not only can Montgomery be a stud for the Red Sox but he also has a playoff resume if Boston got there.

However, there’s something to note here. Montgomery is likely going to fetch a big deal and the Red Sox don’t exactly have the cap space. As insider Jon Morosi noted this week, Boston would likely need to try and trade closer Kenley Jansen and his $16 million contract in order to actually sign Montgomery. Your move Craig Breslow.

Yes, it’s totally insane that Boston, who has a $180 million payroll next season, has to move a player so they can sign another. This is a franchise with skyrocketing ticket prices and no shortage of money. It’s one of the reasons fans are so fed up and annoyed right now.

That being said, the Red Sox can save face by convincing Jordan Montgomery that he should be pitching in Boston when Opening Day rolls around. He’d get the chance to be their ace and lead a staff. That probably won’t happen elsewhere. Will it be enough for Montgomery to choose the Red Sox as his next home? Only time will tell.

If not, the Boston starting rotation could be in for a tough year. With him, they’d at least be better off.