3 Dream Red Sox Additions During the Winter Meetings

With the MLB Winter Meetings kicking off yesterday, it is time to turn the heat on the hot stove all the way up. MLB executives and player agents are all converging in Nashville, and the Winter Meetings have historically been an epicenter for some of the biggest transactions of the offseason.

Of MLB.com's Top 25 Free Agent Rankings, only two free agents have signed (Aaron Nola and Sonny Gray). Of the 30 MLB teams, 18 have yet to sign a major league free agent. Boston is one of those 18 teams. Red Sox fans have been anxiously awaiting new chief baseball officer, Craig Breslow, to make his first big splash in charge. There is a real chance that Breslow makes that splash during his trip to Nashville.

Pitching is the clear-cut priority for Breslow in his first offseason, which will be fine by Boston given the pitching-heavy free agency class.

In the past few years, there has been growing discontent from Red Sox fans towards ownership around the group's perceived unwillingness to spend. The backlash has been so loud that owner John Henry vehemently pushed back in a Q&A, calling it a "false narrative" that the club no longer signs free agents. Last season, Boston ranked 13th in payroll on their way to a third last-place finish in four seasons.

The Red Sox have spent highly in each of their 21st century championship seasons. In 2004 and 2007, they ranked second in payroll, in 2013 they ranked third, and in 2018 they ranked first. "Money can't buy championships" may have some truth, but it definitely hasn't been true with the Boston Red Sox.

Boston executive Brian O'Halloran stated at the end of last season that ownership would be "definitely committed" towards improving the team to win a championship. Until ownership does write a large check this offseason, those words will ring hollow with Red Sox fans.

3. Jordan Montgomery

Since 2021, Jordan Montgomery has been "one of the most consistent starters in the Majors", with a 3.48 ERA across 94 starts. His standout playoff performance for the Texas Rangers on their way to a World Series title also undoubtedly enhanced his free agency stock. Montgomery made six appearances, going 3-1 with a 2.90 ERA and 17 strikeouts.

Montgomery was linked to Boston even before it was reported that he is spending his offseason in the city while his wife completes her dermatology residency at an area hospital. Montgomery has been throwing at nearby Boston College, and Bob Nightengale has reported that this arrangement gives the Red Sox a "slight edge". For the gambling folks, the left-hander is also a +150 favorite to sign with the Sox (if he doesn't return to Texas).

In line with the Winter Meetings schedule, MLB.com Mark Feinsand stated Saturday, "If [Montgomery] finds a deal he likes with the right team, I think he could come off the board this week". In addition to the Red Sox, the Cubs, Mets, Yankees and Rangers are also expected to be in the mix.

Unlike the next two on this list, Montgomery is not a bonafide ace and top-of-the-line starter. The Red Sox need to come out of their offseason with a frontline starter, but make no mistake, Montgomery's role as a middle of the rotation arm would be a valuable addition.