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Will the Boston Red Sox end up selling this trade deadline? It's a question that was ludicrous a month ago. After a 20-6 June, the Red Sox looked like one of the strongest teams in baseball and though they were staring at a wild-card round all along, a three-game series there is a much better bet for good teams than a one-and-done crapshoot. After being on the cusp of the World Series last season, surely chief baseball officer Chaim Bloom would be more aggressive this time around, right? 

Even before their latest skid, the answer was: Not so fast. Back on July 9, the Boston Globe reported the Red Sox were planning to be "cautious buyers," but also noted the possibility of them selling due to a tough upcoming schedule. 

The Red Sox have gone 5-14 in July. They haven't beaten anyone but the Yankees since July 4 and they were embarrassed three straight games recently like no one has since the 1800s. They have fallen to three games out of the third wild-card spot in a very crowded AL field. If they fall a few more games back in the next week or so, we could even see them pivot to selling by the Aug. 2 deadline.

Let's look at both scenarios. We'll discuss first if they get hot and buy, but the highest intrigue lies below in the sellers area. 

If they buy ... 

First base remains a problem. It's a platoon of Franchy Cordero and Bobby Dalbec right now. Last year they ended up moving Kyle Schwarber, a career outfielder (who came up as a catcher), there. According to Baseball-Reference's wins above average by position, only the Tigers have been worse at first base this season among all 30 teams. 

They could sure use a rotation upgrade, too, if they want to make a deep playoff run. Right now this has the makings of patchwork. Chris Sale just broke his finger and while it's possible he comes back late in the season, it's also possible he doesn't. Nathan Eovaldi is back, but he's long been an injury concern. By the same token, can they trust Michael Wacha or 42-year-old Rich Hill? Nick Pivetta's been atrocious in July and his track record suggests it's tough to trust him. 

Every team could stand to add bullpen depth as well. 

Potential targets

Though it seems like the Red Sox should be good enough -- and a heavy-enough hitter in terms of market, financial wherewithal and prospect currency -- to swing for the fences here, "cautious" buying and last year's action suggests that just won't be the case. With that in mind, here are some names that could be on Boston's radar:

  • Josh Bell is a switch hitter who is actually a first baseman by trade. He's hitting over .300 with power on a Nationals team going nowhere, and Bell is a free agent after the season. He'd be a really nice fit offensively and defensively while they wouldn't have to bother with platoons. I really love this fit if they are looking for a temporary boost. 
  • Dominic Smith of the Mets has been connected to the Red Sox in trade rumors and while they could throw him at first, he seems like less of a short-term upgrade and more a quick spring training 2023 project. 
  • Cubs outfielder Ian Happ will hit free agency after 2023 and has become an everyday left fielder, but he's played some first base and has been pretty adaptable in the field in his career. Given the extra year of control, if the Cubs make Happ available, this seems like a decent fit. Remember, Happ is also a switch hitter. 
  • With the rotation, it seems like they should be in on the Luis Castillo and Frankie Montas types, but the hunch here is they will easily be outbid. 
  • Castillo's Reds teammate, however, Tyler Mahle might end up being a palatable option. He's been inconsistent and dealt with injury this season, which lowers the asking price. There's also the upside that saw Mahle pitch to a 3.72 ERA (127 ERA+) with 270 strikeouts in 227 2/3 innings in 2020-21 combined. He's under team control through 2023, so this might fit a longer-term plan for Bloom. 
  • Noah Syndergaard would be a rental and is having a good year with the Angels. Though it seems like the big name, who isn't as good as past reputation suggests, isn't really a Bloom-type target. 
  • José Quintana, on the other hand, hadn't really been good since 2017. The Pirates grabbed him on a $2 million deal this season and he's been productive in the rotation. He could also work in relief and probably wouldn't cost all that much in a trade. 

As for relievers, look at basically any veteran on a non-contending team -- especially since we don't expect the Red Sox to be shopping at high-end prices. 

Of course, all of this is moot if the team unless the Red Sox get back on track soon. 

If they sell ... 

The much more juicy storyline would be the Red Sox as sellers. It would be a market-changer, depending upon how hard they go after it. Look at these pieces. 

  • All-Star shortstop Xander Bogaerts has an opt-out clause at the end of the season and extension talks have gone nowhere. 
  • All-Star DH J.D. Martinez is a free agent after the season. 
  • All-Star third baseman Rafael Devers hits free agency after next season, though surely they won't deal him at age 25 and his injury complicates matters even further. 
  • Eovaldi is a free agent after the season.  
  • Kiké Hernandez, Jackie Bradley, Jr., Christian Vazquez, Michael Wacha, Rich Hill and Matt Strahm are also free agents after the year. 

This all actually makes the Red Sox one of the most intriguing teams to watch on the field in the next 10 days. 

Even if Bloom only wanted to move on from free-agents-to-be, the farm system could make a veritable killing on the trade market.

If things continue on their current path, expect the Red Sox to sell. And if they do, they might resemble last season's Cubs in gutting the roster. Everyone listed above except Devers could be gone. It's definitely a situation worth monitoring, as Bogaerts and Martinez alone alter the landscape of the market and the others have the potential to be important cogs for new teams.