Long-awaited Red Sox target chooses someone else
HOUSTON, TEXAS - OCTOBER 15: Jordan Montgomery #52 of the Texas Rangers looks on against the Houston Astros in the second inning during Game One of the American League Championship Series at Minute Maid Park on October 15, 2023 in Houston, Texas. (Photo by Carmen Mandato/Getty Images)
The Boston Red Sox seemingly had a free-agent starting pitcher in their back pockets. But ultimately, their top target ended up choosing another destination.
Jordan Montgomery has agreed to a deal with the Arizona Diamondbacks, as first reported by ESPN’s Jeff Passan. It’s a one-year deal worth $25 million, with a player option for 2025. Montgomery previously helped the Texas Rangers defeat his new team in the World Series.
The writing may have been on the wall for the Red Sox earlier this month. ESPN’s Buster Olney .@Buster_ESPN said on the @TMKSESPN that Jordan Montgomery’s preference is to sign “in a smaller market like Texas, like St. Louis” but isn’t sure if that opportunity exists.
Well hey, the Red Sox are acting like a mid-market team these days.
Just throwing that out there. pic.twitter.com/QDM5oXXgNN
— Tyler Milliken (@tylermilliken_) March 7, 2024" target="_blank" rel="noopener">said recently on the Michael Kay Show that Montgomery preferred to play in a smaller market. Arizona would certainly qualify, as compared to somewhere like Boston or New York.

ARLINGTON, TEXAS – OCTOBER 28: Jordan Montgomery #52 of the Texas Rangers pitches in the first inning against the Arizona Diamondbacks during Game Two of the World Series at Globe Life Field on October 28, 2023 in Arlington, Texas. (Photo by Carmen Mandato/Getty Images)
There had been hope for Montgomery to ultimately sign with the Red Sox, because, well, he’s living here. His wife is working at an area hospital and he’d spent plenty of time working out around Boston. But clearly, that didn’t mean he had much desire to actually put on a Red Sox uniform.
It does take a certain kind of guy to survive playing in a market with the intensity of Boston, let alone thrive. Even when the team is middling at best, there’s constant pressure from media and fans to perform, and Fenway Park is one of the harder places to play for anyone who doesn’t do well with a high-energy fan atmosphere.
The Red Sox are left with a starting rotation of Brayan Bello, Nick Pivetta, Kutter Crawford, Garrett Whitlock, and Tanner Houck to begin the 2024 season.
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Matt Dolloff is a writer and podcaster for 985TheSportsHub.com. Any opinions expressed do not necessarily reflect those of 98.5 The Sports Hub, Beasley Media Group, or any subsidiaries. Check out all of Matt’s content.
Four exciting Red Sox players to watch this season
Baseball season is here and while the Red Sox had a pretty brutal offseason by all metrics there’s still a few guys on their roster I’m excited to watch this year. We’ll take Rafael Devers out of the equation as I expect him to get back to his old form and be one of the best power hitters in baseball.
Red Sox fans are rightfully pretty upset about the teams lack of moves and mixed messaging this offseason but they are building a farm system and will look to surprise teams this year. Not a position I’m particularly fond of as a Red Sox fan who believes they should never be in the underdog role with their payroll and assets but here we are. So with opening day right around the corner let’s take a look at the four players I’m most excited to watch this season.

Sep 12, 2023; Boston, Massachusetts, USA; Boston Red Sox first baseman Triston Casas (36) bats against the New York Yankees during the first inning at Fenway Park. Mandatory Credit: Eric Canha-USA TODAY Sports
1. Triston Casas
Casas is easily one of the most exciting names on the Sox roster this year and he’ll look to build on a solid season last year and start to establish himself as an all-star caliber player. Last year Casas was one of the few bright spots for Boston hitting .263 with 24 homeruns 65 rbis and an OPS of .856. While these numbers don’t blow anyone out of the water it was a great stepping stone for Casas as he continues to figure out the Major Leagues.
At only 24 years old Casas is still fine tuning his skill set and hopefully with another offseason under his belt we’ll see him start to refine some of his raw power. A 2018 first round pick Casas has been one of the highest touted Sox prospects in recent years and this season will be crucial to his growth, with the lack of firepower in the Sox offense he’ll have plenty of opportunities this year to grow into the player the Sox and fans are hoping he’ll become.

BOSTON, MASSACHUSETTS – SEPTEMBER 12: Masataka Yoshida #7 of the Boston Red Sox fields in front of the Green Monster during the sixth inning against the New York Yankees at Fenway Park on September 12, 2023 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)
2. Masataka Yoshida
Yoshida was one of the other few bright spots for the Sox last season as he showed his hitting prowess early in the season. However the length of the MLB season seemed to wear on Yoshida as he wasn’t used to the travel and number of games played. With a full offseason under his belt in the Red Sox system I expect his durability to increase.
Yoshida also struggled defensively at times last season but I expect him to DH more this season which will also have a positive impact on his performance at the plate. Yoshida showed right away he can hit in the Majors but it’ll be more on how he maintains his body and how much we see him in the outfield this season that could hinder his performance. I also believe Yoshida could benefit by being moved down in the lineup this season and not batting at the top of the lineup as much as he did last season.
Matt, a North Andover, Massachusetts native, has been with The Sports Hub since 2010. Growing up the son of Boston University All-American and Melrose High School hall-of-fame hockey player Steve Dolloff, sports was always a part of his life. After attending Northeastern University, Matt focused his love of sports on writing, extensively writing about all four major Boston teams. He also is a co-host of the Sports Hub Underground podcast and is a regular on-air contributor on the Sports Hub. Matt writes about all New England sports from Patriots football to Boston Celtics and Boston Bruins.