On November 18, the Boston Red Sox did quite a bit of signing, trading and roster shuffling to make room for three pitching prospects they wish to protect from the Rule 5 Draft.

Earlier in the afternoon, Boston traded homegrown reliever Luis Guerrero to the Tampa Bay Rays and designated Josh Winckowski and Nathaniel Lowe for assignment. Less than an hour before the Rule 5 protection deadline, the Red Sox traded lefty reliever Chris Murphy to the Chicago White Sox, first reported by MLB insider Bob Nightengale.

Britt Ghiroli of The Athletic, first reported that the Red Sox received a catcher in exchange for Murphy. Alex Speier of The Boston Globe confirmed that 21-year-old Ronny Hernandez is the return. Murphy is the second lefty reliever Boston has shipped to Chicago in as many years — it traded Cam Booser for pitching prospect Yhoiker Fajardo last offseason.

Boston also traded reliever Brennan Bernardino to the Colorado Rockies to open up a third roster spot, according to Hunter Noll of BoSox Injection and Beyond the Monster. For his fourth trade of the day, Craig Breslow sent flamethrowing pitching prospect Alex Hoppe to the Mariners for catcher Luke Heyman.

It’s nice to hear that the Red Sox will get some catching depth in return for Murphy, but the real reward was the 40-man spot opened up by the day’s many roster moves. Boston has added pitching prospects David Sandlin, Shane Drohan and Tyler Uberstine to the 40-man roster to protect them from the Rule 5 Draft, according to Chris Cotillo of MassLive.

Red Sox trade Chris Murphy to White Sox, Brennan Bernardino to Rockies, protect pitching prospects David Sandlin, Shane Drohan and Tyler Uberstine from Rule 5 Draft

The Red Sox had to do so much maneuvering to open up the three roster spots that will be occupied by Sandlin, Drohan and Uberstine that Sandlin was the only prospect certain to be protected a few days before the deadline. Sandlin is Boston’s No. 10 prospect and could make the major league roster out of spring training after a great season between Double-A and Triple-A.

Sandlin posted a 4.50 ERA with 107 strikeouts and 40 walks over 106 innings between the Sea Dogs and WooSox. His ERA was severely heightened by his short stint in Triple-A because he transitioned to a relief role in anticipation of a potential call-up to the major leagues to assist the Red Sox with their playoff push. Sandlin clocked a 3.61 ERA and 1.18 WHIP over 82.1 innings with Portland and a 7.61 ERA and 2.03 WHIP in 23.2 innings — 15 relief appearances and one start — in Worcester.

Drohan and Uberstine, both 26, are also starting pitching prospects, and they would’ve been taken in the Rule. Draft had the Red Sox not protected them. Drohan logged a 2.27 ERA, 1.01 WHIP, 67 strikeouts and 16 walks over 47.2 innings in Triple-A last season. Uberstine reached Triple-A for the first time in 2025 and clocked a 3.56 ERA and a 1.33 WHIP with 102 strikeouts and 37 walks over 91 frames.

The Red Sox moved on from quite a few veterans to protect their up-and-coming arms, which shows just how confident they are in their pitching pipeline. Hopefully, Sandlin, Drohan and Uberstine get a chance to make a difference in the major leagues this coming season.