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July 26, 2021 at 12:00 PM

Red Sox Trade Deadline Primer

Trade chips likely to come from 40-man jam, complexes as deadline approaches

For the first time since Chaim Bloom became Chief Baseball Officer of the Boston Red Sox, they are in the position to be buyers at the trade deadline. The Red Sox and Rays are going to be fighting for the division down the stretch, with the Yankees also not to be counted out. With the Rays already adding Nelson Cruz, there will be even more pressure on the Red Sox to make a move and address some of their weaknesses. 

The three areas that the Red Sox seem most likely to target for improvement are first base, a utility bench spot and pitching. At first base, they could use a left-handed hitter to complement the right-handed hitting options they have there.  For the bench, neither Marwin Gonzalez nor Danny Santana has established themselves in the super utility bench role, as both have struggled at the plate. Lastly, every team needs pitching depth, and the Red Sox are no different. They could use a reliever to help ease the burden on some of their late-inning arms, as Matt Barnes, Adam Ottavino, Garrett Whitlock and Josh Taylor are all pushing towards career highs in innings pitched. 

The Red Sox also could look outside of those three areas, as Bloom has shown he is always looking for ways to upgrade the roster both in the short-term and long-term. If they made a move for the long-term, all bets are off as to who would be on the table. If they choose to focus on smaller deals and rentals, however, there are three types of prospects they will likely look to deal from: 

1. Prospects on the 40-man roster 
2. Prospects eligible for the Rule 5 Draft this coming offseason 
3. Prospects in Rookie ball

Prospects on the 40-man Roster

As of today, the Red Sox have eight minor leaguers on their 40-man roster. Connor Seabold and Jay Groome are the top prospects from that group, and it is unlikely the Red Sox would deal them for a rental. Seabold especially could serve as major league depth down the stretch. Groome is a borderline top 10 prospect in the system (post-draft) who is in the midst of the best stretch in his career and still has significant upside. He still is several years away, so you cannot rule him out as part of a trade, although it still seems unlikely. Jonathan Araúz & Connor Wong are major league depth and have more value in that role than they likely would in a trade, also making them unlikely to be moved. 

The other four prospects are Marcus Wilson, Jeisson Rosario, Hudson Potts and Ronaldo Hernandez. None of those four will make an impact in Boston this year and thus could be potential trade candidates to get someone who might help now. Moving some of those players would also help going forward, since the Red Sox have a 40-man roster crunch coming up in the offseason, which I’ll discuss more below. All four are blocked by better prospects. Wilson and Rosario blocked in the outfield by Alex Verdugo, Jarren Duran, Kiké Hernandez, Hunter Renfroe and Franchy Cordero, who are all under team control for multiple seasons. Potts is blocked at third base by Rafael Devers, while a move across to first base is unlikely with the presence of Triston Casas. At catcher, the Red Sox have the least depth of the three spots, but Hernandez is not a lock to stick behind the plate and has significant development remaining. All four of those players could draw interest elsewhere, and moving them would not put a major dent in the depth Bloom has built up since he took over. 

Rule 5-Eligible Prospects

The Red Sox have a 40-man roster crunch coming this off-season, and one way to combat that is to move some of the prospects who are eligible to be added. We saw this exact type of a deal to alleviate such a log jam last year, when the Padres dealt Rosario and Potts to the Red Sox for Mitch Moreland. They didn’t have room to add Rosario and Potts, but the Red Sox did. 

You can find a full list of Rule 5 eligible players for this coming offseason here. As of now, I believe there are three locks to be added: Jeter Downs, Brayan Bello and Gilberto Jimenez. In the next tier are two players: Josh Winckowski and Thaddeus Ward. Winckowski has pitched well in Double-A and fits the profile of a player who would be selected if left unprotected. Ward is a wildcard. He seemed to be a lock to be protected coming into the year, but he had Tommy John surgery in early June. He will miss most, if not all, of 2022, and he will be 26 years old in 2023 with eight career innings above High-A. The decision of whether to protect him will be fascinating, since he would take up a 40-man spot for two offseasons with no chance of helping the major league team, but left unprotected could be targeted in Rule 5 by a team who could place him on the 60-day IL while he rehabbed in the hope it could keep him active for 90 days in MLB before optioning him upon his return. 

After those five players, there are still another seven or eight players who would be considerations for protection, the most interesting of which to me are Kutter Crawford, Durbin Feltman, Frank German, Pedro Castellanos and Ryan Fitzgerald. Crawford dominated Double-A in his return from October 2019 Tommy John surgery before a recent promotion to Worcester. He could pitch his way into that group with Winckowski and Ward if he keeps up his pace in Triple-A. Castellanos and Fitzgerald are having excellent seasons with Portland, but have relatively low ceilings and are behind other prospects ahead of them at their respective positions such as Casas and Downs, which explains why Castellanos has exclusively played the outfield this season and why Fitzgerald is being groomed for a utility role, playing second, third, left and center in addition to his primary home at shortstop. German and Feltman fall into a bucket with players like Alex Scherff, Kaleb Ort and Jose Adames as potential MLB relievers at some point in the next year or two. The Red Sox do not have room to protect most, if not all of these players, so it would make sense to deal from this group to help the major league team this year.

Rookie-ball Prospects

Every year, lottery ticket types in the complex leagues are involved in trades, and the Red Sox have a considerable amount of talent in both the Florida Complex League and Dominican Summer League that would interest other teams. Both of the complex leagues started their seasons over the last month, giving scouts their first opportunity to see many of those players in game action since 2019, if at all. As a result, teams now have new information on these players which would make them more comfortable acquiring them in a trade. An incomplete list, in no particular order, of interesting players who I've gotten reports on that would be of interest to other teams include Wilkelman Gonzalez, Eduardo Vaughan, Nathaniel Cruz, Brainer Bonaci, Eddinson PaulinoLuis De La Rosa and Bryan Gonzalez in the FCL and Allan CastroYizreel Burnett, Luis Ravelo, Rivaldo Avila, Kelvin Diaz, Johnfrank Salazar, Jhostynxon Garcia and Juan Chacon in the DSL. 

Photo Credit: Danny Santana, Marcus Wilson, Pedro Castellanos and Brainer Bonaci by Kelly O'Connor.

Ian Cundall is Director of Scouting for SoxProspects.com. Follow him on Twitter @IanCundall.