Previewing the Rule 5 protection deadline for the Red Sox

The next deadline that Boston Red Sox fans need to care about comes at the end of this week as teams have until Friday to protect eligible players from the Rule 5 Draft. As a quick primer for those not clear on how the draft works, eligible players are those who either: have been in pro ball for at least four years and signed their first contract at 19 years or older, or have been in pro ball for at least five years and signed their first contract at 18 years or younger.

The draft, which takes place on the final day of the Winter Meetings (usually, at least; I’m not sure what the plan is if a lockout cancels the event this year), requires players taken to remain on their new team’s active roster for the entire upcoming season or else their former team has a chance to take them back in their minor-league organization. Players must be added to the 40-man roster prior to Friday’s deadline to be ineligible for selection.

Red Sox fans should certainly be familiar with the draft at least on a basic level as it is how the organization acquired Garrett Whitlock, who was of course one of the very best pitchers on the roster this past year. In fact, Chaim Bloom has had some success in this draft in his two winters with the organization, not only with Whitlock but also taking Jonathan Araúz the year before and keeping him on the roster all year (with some help from a shortened season). He’s also found some good players in the minor-league portion of the draft, though for the purposes of this post we’re only going to think about the major-league portion.

Instead, we want to focus on who the Red Sox will add to their own 40-man roster. Let’s start with taking a look at the potential candidates, of which there are many, and give reasons why each will and will not be protected.

Jeter Downs, 2B/SS

Why he’ll be protected: Even coming off a disappointing season, Downs is still a potential all-around talent who plays up the middle, and he should be ready for the majors at some point next season.

Why he won’t be protected: He’s coming off a bad season, and the fact that he’s already been traded twice indicates there may be bigger flaws here than originally acknowledged.

Verdict: Lock to be protected.

Josh Winckowski, RH SP

Why he’ll be protected: He’s right on the doorstep of the majors and has the kind of talent to be a reliever or back-end starter sooner than later.

Why he won’t be protected: There’s no real standout skill here, and that can be the kind of profile that works in the minors but hits a wall once a pitcher reaches the highest level.

Verdict: Lock to be protected.

Brayan Bello, RH SP

Why he’ll be protected: Bello has as much talent as anyone in the Red Sox system, and finally showed some real consistency in 2021. He’s also in the upper levels of the minors.

Why he won’t be protected: There is still a lot of raw talent here, and he struggled with his consistency once again in the second half after getting to Double-A.

Verdict: Lock to be protected.

Thad Ward, RH SP

Why he’ll be protected: When healthy, he looked to have perhaps the best mix of upside and safety among Red Sox pitching prospects and had reached the upper levels of the minors.

Why he won’t be protected: He underwent Tommy John surgery this past summer and teams may not be willing to use a 40-man spot with this lack of certainty.

Verdict: Likely to be protected.

Kutter Crawford, RH SP

Why he’ll be protected: He took a big step forward this year and stayed in the rotation through the entire season, all while showing he can miss bats. He also made his major-league debut.

Why he won’t be protected: His ceiling is still an open question, with many still seeing him as a future reliever, and perhaps not a back-end one.

Verdict: Borderline case, probably closer to protection.

Gilberto Jimenez, OF

Why he’ll be protected: In terms of pure talent and upside he’s still among the best prospects in the system, and he could be kept on an active roster as a fifth outfielder given his speed and defense.

Why he won’t be protected: He hasn’t played above A-Ball, and even there he was more fine than great.

Verdict: Borderline case, but likely to be protected.

Durbin Feltman, RH RP

Why he’ll be protected: He finally appeared to be making good on the draft day upside this past season, especially once he got to Triple-A, and should be able to contribute in a big-league bullpen in 2022.

Why he won’t be protected: He still hasn’t looked completely dominant in the minors, and command issues still pop up from time to time.

Verdict: Probably more likely than not to be protected.

Kaleb Ort, RH RP

Why he’ll be protected: After being selected in the minor-league portion of the draft last winter, he was Worcester’s best reliever for pretty much the entire season.

Why he won’t be protected: There just isn’t the same kind of upside as there is with some of the other names on this list, and they can only protect so many names.

Verdict: It’s possible, but unlikely.

Zack Kelly, RH RP

Why he’ll be protected: He was dominant in 2021 across Double-A and Triple-A, striking out over 13 per nine innings in both levels, and has the kind of profile teams will want to target in this draft.

Why he won’t be protected: There’s not a ton of name value and the ceiling isn’t big, plus you can only protect so many players.

Verdict: The potential surprise protection for this year.

Kole Cottam, C/1B

Why he’ll be protected: He’s done nothing but hit in the minors, and is getting a little bit of a spotlight for scouting departments in the Arizona Fall League.

Why he won’t be protected: The Red Sox already have four catchers on the 40-man, and adding a fifth may be a bridge too far.

Verdict: Unlikely to be protected, but could be drafted.

Frank German, RH RP

Why he’ll be protected: The raw stuff is that of a major-league reliever, and once he was converted into that role the potential became more clear.

Why he won’t be protected: We only saw flashes in 2021, but the season as a whole was more discouraging than encouraging.

Verdict: Unlikely to be protected

Ryan Fitzgerald, INF

Why he’ll be protected: He has an all-around skillset in the infield and can be a good defense-first bench player with a little bit of skill at the plate.

Why he won’t be protected: There’s virtually no upside, and this is a kind of player who is easier to keep on an active roster in theory than in practice.

Verdict: Unlikely to be protected.

Pedro Castellanos, 1B/LF

Why he’ll be protected: He showed enough of that power to show that he at least will be solid in that department, and he expanded his versatility by spending the year in the outfield.

Why he won’t be protected: The power is still more fine than great, and his versatility is only at positions low on the defensive spectrum.

Verdict: Unlikely to be protected.

Franchy Cordero, OF

Why he’ll be protected: Drooling over the potential of Cordero will never go out of style, and he of course has major-league experience.

Why he won’t be protected: Teams could have claimed him off waivers already earlier in the winter, and they could have optioned him in that scenario. It would be weird to pass then but then draft him in the Rule 5.

Verdict: Unlikely to be protected.

Ceddanne Rafaela, UTL

Why he’ll be protected: He’s the kind of player good teams are looking for now as a good athlete who can play multiple premium positions in both the infield and outfield.

Why he won’t be protected: He’s still raw and in the low minors, and the offensive skillset at this point is likely a stretch for the majors.

Verdict: Unlikely to be protected.

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So, who will be protected? As of right now, the Red Sox have 33 players on their 40-man roster, which means they can add up to seven players to the roster. That said, they are also obviously planning on bringing in some new faces that will need roster spaces too. Given that, and also some players currently on the roster who could be removed, adding somewhere from six to eight players is still reasonable, even if it’s a lofty number. Ultimately, I think the following players will be protected.

• Jeter Downs
• Josh Winckowski
• Brayan Bello
• Thad Ward
• Kutter Crawford
• Gilberto Jimenez
• Durbin Feltman
• Zack Kelly

What say you?