OTM Roundtable: Rule 5 decision time

It’s a big day on the MLB offseason calendar, as teams have until later this evening to protect any eligible prospects from the Rule 5 draft. In order to do so, teams must add these minor leaguers to the 40-man roster. The Red Sox have an inordinate number of potential players to protect, so this is one of the more interesting Rule 5 deadlines for them in recent memory. For this week’s roundtable, I asked the staff who they would protect.

Scott Neville

Brayan Bello should be added to the 40-man roster. The 22-year-old started the year in High-A ball where he went 5-0 with a 2.27 ERA with 45 strikeouts in 31 ²⁄₃ innings (six starts). He was rewarded with a call-up to Double-A, where he would spend the majority of his year. Bello went 2-3 with a 4.66 ERA for the Portland Sea Dogs but still showed promise. His arm still proved to be electric, striking out 87 batters in 63 ²⁄₃ innings. This right-hander is one of the most exciting pitching prospects this organization has had in years, granted the competition hasn’t been steep.

Josh Winckowski is another player that should be protected. The right-hander tops out at 97 mph as a starter and could potentially throw even harder in relief. After a strong showing in Double-A, the 23-year-old was promoted to Triple-A for two starts, where he had a 2.25 ERA in 12 innings with 13 strikeouts and three walks. He’s started 72 of the 77 games played in the minors but I could see Winckowski making a major-league debut in 2022 out of the bullpen. Regardless of what innings he pitches, Winckowksi is a promising player worth protecting.

Jeter Downs is an obvious automatic protection so I don’t even need to write about it. Other players to consider are Kutter Crawford, Kaleb Ort, and Pedro Castellanos.

Keaton DeRocher

The names that initially come to mind are Jeter Downs, Gilberto Jimenez, Brayan Bello, Thad Ward, and Durbin Feltman. Feltman is probably a long shot here, but I think the Red Sox believe in him and he did improve his numbers this past season, most notably getting his walk rate back under control between Double-A and Triple-A. With the Red Sox bullpen in the shape it’s in and the strides he made to improve, I think he’ll be added to the 40-man roster.

Avery Hamel

My list of who the Sox should protect from Rule 5 this year:

Kutter Crawford, Durbin Feltman, Brayan Bello, Jeter Downs, Gilberto Jiminez, Thad Ward, and Josh Winckowski.

Another good candidate for protection would be Kaleb Ort, but considering his lack of rank on Sox Prospects, I chose to leave him off of this list.

Bello, WInckowski, and Crawford are some of Boston’s highest-ranked pitching prospects, and all of them have the chance to make an impact on the big league level relatively soon. Feltman was my vote for most improved throughout the farm system in the 2021 season, and his vast improvements over the last two years more than justify his protection from the draft. Ward is recovering from Tommy John that he received earlier this year, but before that, he was one of the Sox’s brightest lights in the system and seems to be expected to rebound relatively well. Jiminez and Downs are two of Boston’s top-ranked position players and both are still very young and will have the opportunity to develop even further by being protected this year.

Michael Walsh

The Red Sox definitely have a few decisions to make before today’s deadline. They have quite a few interesting names that are eligible for the Rule 5 Draft, and some of the ones that stand out to me are: Brayan Bello, Kutter Crawford, Jeter Downs, Durbin Feltman, Gilberto Jiminez, Thad Ward, and Josh Winckowski. Certainly, Downs is the most important of those, but all of them should absolutely warrant consideration.

Bayleigh Von Schneider

The Red Sox 40-man roster is currently set at 33. With that being said, they will be adding free agents this offseason. For the sake of argument, let’s just talk about the players the Red Sox should be finding some way to protect. Jeter Downs, Durbin Feltman, Gilberto Jimenez, Kutter Crawford, Kaleb Ort, Thaddeus Ward, Brayan Bello, Josh Winckowski, and Pedro Castellanos are all Rule 5 eligible this December and could warrant protection.

Brendan Campbell

If they don’t want to risk losing him in the Rule 5 Draft, the Red Sox should add Durbin Feltman to their 40-man roster by Friday’s deadline. Feltman may not be as highly touted as he once was when coming out of TCU in the third round 2018 amateur draft, but I believe there is still plenty of upside there. This past season, the right-handed reliever earned himself a promotion to Triple-A Worcester in late July after beginning the year at Double-A Portland.

With the WooSox, Feltman posted a 2.59 ERA and 3.40 FIP to go along with 25 strikeouts to just four walks over 17 relief appearances spanning 24 1/3 innings of work. He cut down on his walk rate significantly upon arriving in Worcester and very much benefited from it in his first exposure to Triple-A hitting.

Feltman, who does not turn 25 until next April, could play a role within the Red Sox bullpen at some point next season. Of course, things could change drastically if he is left unprotected and then selected by another team in the Rule 5 Draft. That said, the hard-throwing 24-year-old should be one of the several minor-leaguers Boston protects and adds to their 40-man roster by the end of the week.

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Mike Carlucci

Without doing a lot of 40-man roster math, the Red Sox have a few strong candidates for protection in the Rule 5 draft. While it’s not usually a big issue these days given the changes to the Draft over the years, as we saw in Garrett Whitlock, there are players out there teams should have protected. We’ll start with Jeter Downs. The key prospect in the Mookie Betts trade, coming off a huge Arizona Fall League and playing an infield position the Sox could use…yeah, he’s protected. Same for pitcher Josh Winckowski. A big fall to help his value. Two more pitchers? Brayan Bello and Kutter Crawford. Bello because he’s still young (22) and Crawford because of his solid season at Double A after two years of Tommy John interruption.

The Sox will definitely need more than five starters and he should be able to fill in here and there. Thaddeus Ward (Tommy John) and Kaleb Ort “Cloud” could both factor into the mix as well. But we’re starting to protect a lot of guys at that point. Coming off the injury might mean Ward is less desirable to other teams, but, of course, maybe not. The biggest story here is that the Red Sox once again have a farm system that other teams might try to poach. The top guys are all at a stage before they need to be protected but that next level? There’s some good stuff and guys they could probably trade if there’s a roster crunch.

Bob Osgood

There are as many as five pitchers that seem like near-certain adds to the 40-man roster on the surface but with 15 pitchers out of 33 on the current roster, it is hard to see all of them getting added without a couple of drops and a trade or two. The Red Sox will almost certainly add one or two starting pitchers and a couple of more relief pitchers via free agency and it’s hard to envision the team entering the season with more pitchers than hitters on the 40-man roster.

I believe that Jeter Downs (2B), Brayan Bello and Josh Winckowski (Ps) are locks. Kutter Crawford (P) is a near-lock having continued his breakout minor-league season with four dominant starts in the Dominican Winter League and, while he’s surely a couple of years away from being ready, I put Gilberto Jimenez in the near-lock category as well as the elite speed and above-average defense in center field seems too valuable to risk losing before his bat catches up.

Even if the Red Sox remove Phillips Valdez and Austin Davis from the 40, that would put the Red Sox at 16 pitchers before free agency. If they do add one more, I believe it will be Thaddeus Ward who likely has the most long-term upside of all of the remaining pitchers, which would mean a total of six players are added to the 40-man roster. While Durbin Feltman and Victor Santos are possibilities out of the bullpen, I lean towards them both being left unprotected and there is always the possibility that the Red Sox make a selection of a similarly talented arm in the Rule Five draft from another team.

Jake Devereaux

This is a bit of an uncommon year for the Red Sox considering they have so many players that would generally be deserving of Rule 5 protection. With that being said, I think that they will end up protecting seven total players. I believe they will protect: Jeter Downs, Josh Winkowski, Kutter Crawford, Gilberto Gimenez, Bryan Bello, Thad Ward, and Durbin Feltman. Ward and Feltman are the borderline cases for me, but I believe the first five are a lock. Ward is a bit older and won’t pitch this year making him an interesting case and Feltman still hasn’t quite regained the stuff he showed when he was in college. Ultimately I believe they have enough flexibility with 33 men on the current 40-man roster and three players in Hudson Potts, Jeisson Rosario, and Tim Locastro who they can easily part with.