MLB Trade Deadline 2023: NESN Debates Who Red Sox Should Target

The Boston Red Sox have been Major League Baseball’s best team in July, setting themselves up to buy at the Aug. 1 trade deadline.

Red Sox chief baseball officer Chaim Bloom has made his intentions clear, putting together a clear blueprint of Boston’s approach to the deadline and making his first move — shipping Kiké Hernández back to the Los Angeles Dodgers for a pair of pitchers who could become contributors in 2023.

The possibilities are endless for Boston, giving it an opportunity to make a big splash. Keeping that in mind, here’s who the NESN Digital team wants to see the Red Sox add in advance of a potential playoff run.

Ricky Doyle: Tim Anderson, SS, Chicago White Sox
Anderson has been bad this season. Like, really, really bad. And his free-swinging track record, his ugly underlying metrics and his below-average defense are serious causes for concern. Maybe he just stinks now, and the Red Sox, among others, will want nothing to do with him before the trade deadline.

But we’re talking about a two-time All-Star and a former batting champion who was solid as recently as last season and who should theoretically be in his prime at age 30. This could be a good buy-low opportunity for a club in desperate need of middle-infield help, so long as the White Sox are willing to absorb some of the money still owed to Anderson this season.

Do the Red Sox have more pressing needs? Of course. Both the rotation and the bullpen could use a boost. But for the purpose of this exercise, let’s have a little fun and dream of the Anderson of old. If it worked, Boston even could retain him beyond 2023 as a placeholder for Marcelo Mayer or Nick Yorke.

Tim Crowley: Justin Lawrence, RHP, Colorado Rockies
The Red Sox seem to be in the market for a right-handed reliever to add with Chris Martin and Kenley Jansen at the back of the bullpen. Lawrence is in the middle of a career year with Colorado, posting a 3-3 record and a 2.63 ERA. With a dominant sweeper (averages 14.4 inches of horizontal break) and an unconventional arm slot, Lawrence adds further depth and dominant stuff to an already solid Boston bullpen that also helps break up a crowded group of left-handed relievers. 

Jason Ounpraseuth: Michael Lorenzen, RHP, Detroit Tigers
The Red Sox need depth in the rotation, and Lorenzen is a good rental target for the rest of the season before he becomes a free agent next year. He made the All-Star Game this year and still is in form to help Boston make a push for the postseason.

Sean McGuire: Jack Flaherty, RHP, St. Louis Cardinals
The 27-year-old Flaherty is on an expiring contract and thus should be more in line with the price that Red Sox chief baseball officer Chaim Bloom is willing to give up. Flaherty has a 3.03 ERA in his five starts in July and a 4.43 ERA in 20 starts this season. Bolstering the starting rotation should be one of the areas for improvement ahead of the deadline, and Flaherty makes sense given his upside.

Keagan Stiefel: Jordan Montgomery, LHP, St. Louis Cardinals
James Paxton is the only left-hander out of the Red Sox’s current rotation options, so it would behoove Bloom to target a southpaw at the deadline. Montgomery might be the best available (that wouldn’t cost the farm). Plus, it would be hilarious to see the former Yankee help push the Red Sox past New York and into Wild Card positioning.

Ben Watanabe: Flaherty OR Montgomery, St. Louis Cardinals
Man, do the Cardinals stink. Playing the Nationals and White Sox helped St. Louis get right a little bit, but this is a team struggling to keep its head above water — and the Red Sox should take advantage. Flaherty is cheaper, but Montgomery is probably better (and also left-handed). Either would be an upgrade over what the Red Sox have had to work with due to injuries on its staff.

Mike Cole: Montgomery AND SS Paul DeJong
The Cardinals look like a perfect trade partner for the Red Sox, and it might make sense for both sides to do a package deal with Montgomery and DeJong. Montgomery is a strike-thrower who has really good stuff. He doesn’t strike out a ton of guys, so if more balls are in play, you need to upgrade the defense, which DeJong does. DeJong at short and Trevor Story at second base would be a massive improvement up the middle, too.