The Rule 5 Draft Approaches: Who Should the Red Sox Protect?

The offseason is officially in full swing, and the free agent and trade markets will begin to heat up as teams finalize their in-house talents. One final area regarding the 40-man roster that will need to be decided upon by tonight is protecting prospects Rule 5 Draft. For those who may not know, the Rule 5 Draft is a draft where MLB organizations can select players who are not on another team’s 40-man roster. However, players selected in this draft have to remain on the active roster for the entire season, barring time on the injured list. Players who were signed at 18 years old or younger are eligible for the draft after five seasons, and players who signed at 19 years old or older are eligible after four seasons.

There is also a minor league phase where players in Double-A or lower can be drafted for $24,000 per player to play for the drafting organization’s Triple-A team.

Last offseason, the Red Sox added two players to the 40-man to protect them: pitcher Hunter Dobbins and outfielder Jhostynxon Garcia. Both players wound up playing in the majors with Boston during the 2025 season.

The Red Sox have likewise been benefactors from this draft, as two key members of their bullpen were acquired in such a fashion. Garrett Whitlock was taken during the 2020 Rule 5 Draft from the New York Yankees, while Justin Slaten was taken in the Rule 5 Draft by the New York Mets from the Texas Rangers and was immediately traded to Boston. Boston has also seen various prospects lost over the years, including the loss of Angel Bastardo, a pitching prospect taken in the 2024 Rule 5 Draft by the Toronto Blue Jays.

Currently, the Red Sox's 40-man roster is full due to the addition of players who had ended the season on the 60-day injured list. For the Red Sox to protect any of their eligible prospects, they would need to open up a roster spot. And they may need to clear up a few spots just like last season.

As it stands, the team has 42 prospects eligible for the draft, though most won't be considerations during the major league portion. It isn’t ideal to develop prospects and have them taken by another team, but fortunately for the Red Sox, most of their top prospects have either graduated to the big league club or have been packaged in trades for talent.

However, there are still a few names that bring into question whether the Red Sox should protect them or not. We’re going to break down these players and see why they may not want to be lost.

Likely To Be Added:

Unlike last season, there is really only one player who is likely to be added to the 40-man roster this time around.

RHP David Sandlin (MLB Pipeline #9 Red Sox Prospect)

Sandlin came over to the Red Sox in a spring training trade with the Royals in 2024, turning a surplus in middle relievers into an interesting pitching prospect. His first season had its share of ups and downs as he split the year between High-A and Double-A, finishing with some less than ideal stats.

Despite starting 18 games, Sandlin only managed to toss 57 1/3 innings in that span. What did impress, however, was his ability to generate strikeouts, as he got 82 batters to fan. While he wasn’t going deep into games, Sandlin’s stuff did flash the potential of an impact reliever thanks to his fastball.

The 2025 campaign yielded a step forward, Sandlin cruising in Portland for most of the season. Through his first 17 appearances, he had tossed 82 1/3 innings with an ERA that was nearly two runs lower than his final 2024 number at 3.61. While his strikeouts took a step back (only 86 in those 82 1/3 innings), Sandlin was beginning to look more like a professional pitcher who could locate his stuff and pitch to contact when necessary. This change in demeanor had many wondering if the Red Sox would bring him up to Boston for the stretch run to help out in some form.

The idea was floated around as the team transitioned him to the bullpen upon his promotion to Triple-A. Unfortunately, he struggled with the transition, allowing 19 earned runs in 18 2/3 innings out of the Worcester bullpen.

Despite his struggles, Sandlin has showcased the potential of a major league arm and will only be 25 at the start of spring training. It wouldn’t be a surprise if another team took a flier on him if he were available. The Red Sox would be wise to protect him from being poached by another team.

Coin Flips

Besides Sandlin, there isn’t a definite player that seems to be a lock to be taken in the Rule 5 Draft. While no team wants their developed prospects pilfered, the Red Sox wouldn’t be losing much should another team want to take a risk. However, there are a couple players that the team may want to protect just to play it safe after how their 2025 seasons went.  

RHP Tyler Uberstine

Uberstine was a 19th-round selection back in the 2021 MLB Draft and hadn’t done much to write home about prior to 2025. His first season in 2022 saw him finish the year with seven starts with High-A Greenville where he flashed some potential thanks in part to 35 strikeouts in 33 1/3 innings pitched. Unfortunately, he would go on to miss all of 2023 and most of 2024 due to Tommy John surgery, making 2025 his first full season since his debut year.

Despite that prolonged layoff, Uberstine pitched rather well, finishing this year with a 6-5 record in 25 games between Portland and Worcester. Tossing 120 1/3 innings, he also blew past his previous career-high workload while striking out 137 batters. That strikeout per nine figure of 10.1 will intrigue a lot of teams this winter.

The Red Sox have many other pitching prospects ahead of Uberstine on the depth chart, and because of that, it’s unlikely they’ll add him to the 40-man roster. A team looking for a young, cost-controlled pitcher might take a risk on him due to his strikeout numbers alone, and the Red Sox probably wouldn’t worry too much unless there’s something in his underlying metrics they really love.

RHP Yordanny Monegro (MLB Pipeline’s #27 Red Sox Prospect)

Much like with Uberstine, Monegro is below a few pitchers on the depth chart and will miss most, if not all of 2026 after undergoing Tommy John surgery near the end of August. That alone is why he might be at high risk of being picked in the Rule 5 Draft, as another talented Red Sox arm was taken in this manner in 2024 (Bastardo) knowing that he could be stashed on the 60-day injured list all season.

Monegro is young, as he won’t turn 24 until next October and while his ceiling right now looks like a middle reliever, he flashed potential during his time in the rotation in 2024 and in 2025 before his injury. Despite making just nine appearances in 2025, the right-hander tossed 33 2/3 innings and struck out 49 batters while walking just eight, good for a walk to strikeout ratio of 2.14 and a strikeout per nine of 13.10.

Monegro's best pitch is his slider, which averages between 85-88 mph and is thrown more than any other of his pitches. His fastball, on the other, hand seems to be a work in progress, as his four-seam sits between 94 and 96 mph but he lacks proper command and control of it.

Because of the elbow surgery, Monegro is a prime draft-and-stash candidate for a few teams who might be interested in seeing how he develops, especially as they wouldn’t need to keep him on the 26-man active roster unlike other Rule 5 picks. And because he would make it through the 2026 season without being demoted, whatever team takes him would then be free to send him to the minors in 2027 to continue his development without worry of having to send him back to his original organization.

The Red Sox could do the same, placing him on the 40-man roster to protect him and then placing him on the 60-Day injured list the moment it’s possible. Though, that would require them to use a 40-man spot on him all offseason. There’s a good chance they take a risk and leave him unprotected.

Again, the Red Sox have a total of 42 prospects who are eligible for the Rule 5 Draft, but unlike past seasons, there aren’t many names who stand out as likely candidates to be selected. Beyond Sandlin, the team may comfortable leaving everyone else unprotected.