The trade deadline has come and gone, and Boston Red Sox fans came out of it feeling pretty disappointed.
A big reason for that disappointment was the inability to acquire ace Joe Ryan from the Minnesota Twins. To be fair, that wasn't completely Boston's fault — it reportedly offered plenty, and MLB on FOX jumped the gun and claimed the deal was done. That made the subsequent Dustin May deal underwhelming to a lot of people.
In the end, they acquired left-handed reliever Steven Matz from the St. Louis Cardinals for prospect Blaze Jordan and starting pitcher Dustin May from the Los Angeles Dodgers for prospects James Tibbs III and Zach Ehrhard. Those moves aren't bad, but they didn't instill excitement in Boston fans. However, there's always that old cliche of "sometimes the best moves are the ones you don't make."
Openly, I was pretty upset about losing Blaze Jordan. However, Jordan didn't seem to have a ton of support in the system. He was also available in the upcoming Rule 5 draft in the offseason. Boston traded him now for a piece that makes a strong bullpen even better.
Which prospects were the Red Sox particularly smart (or lucky) to hold onto at the 2025 trade deadline?
5 prospects the Red Sox were smart to hold onto after the deadline
Payton Tolle
Payton Tolle is one of the prospects rumored to be in the package offered for Joe Ryan. He's the big reason I added the "or lucky" stipulation.
Tolle has the feel of someone who Red Sox fans wouldn't have to wait long to regret. The left-handed pitcher dominated High-A, flew through Double-A (27 innings), and is scheduled to make his Triple-A debut sometime this week.
Tolle is a massive human being (6'6", 250 lbs) who gets ridiculous extension on his release. That makes his fastball attack hitters much quicker than you'd imagine. It was a big reason he was drafted so high (second round) in 2024. His 91 MPH fastball appeared much faster than that. Fast forward to August of 2025, and Tolle can hit 99 on his fastball. His secondary pitches have taken a leap as well (particularly since he was promoted to Double-A).
There is a very real chance that Tolle could factor into Boston's bullpen before the end of the regular season. His fastball alone would play at the major league level and lead to some electric outings as a reliever.
Not only could Tolle help the team make a postseason push in 2025, but he'll be fighting for a spot on the Opening Day rotation in 2026.. Tolle has the perfect makeup to be a dominant pitcher in the Major Leagues.
Ryan has become a dog in 2025, but Tolle has the potential to be even better. He's seven years younger, has more team control, and can still help the team compete this season.
Yes, Ryan more than likely would be the better option right now. Boston fans would be wincing in pain every time Tolle pitched in a different uniform for the rest of his career if he were moved, though. Keeping him can still help short term and will be a massive positive for the next decade-plus.
Justin Gonzales
It's hard to be higher on Justin Gonzales than I am. Gonzales is listed at 6'4", 210 lbs, but it's hard to believe the height is correct. He tends to tower over teammates.
The right-handed hitter has next-level raw power and has been smoking the ball in Single-A. He's slashing .280/.370/.396 with 16 doubles, two triples, and three home runs at the level. He's driven in 25 runs, scored 37 more, and stolen 10 bases.
Gonzales has an advanced eye. Not just for his age, but in general. Salem's ballpark has also stolen quite a few home runs from him. It feels like a certainty that he'll start hitting bombs in bunches once he gets promoted to High-A Greenville (which should happen before the end of the season).
Gonzales's value will only grow the longer the Red Sox keep him in their system. He has the chance to become an uber-prospect in quick succession. Only 18, Gonzales is already impressing in Single-A. He essentially skipped the FCL (one game at the level) and could fly through the minor leagues due to his power/eye combination. Gonzales could continue to fill out, which would hurt his athleticism. However, it should add even more to his power potential.
If the Red Sox traded Gonzales at the deadline, he likely wouldn't have yielded too much. He's a teenager, not in the top 100, as far away from the majors as you can possibly be in affiliated baseball. Boston would've had to use him as a trade enhancer. If they hold off just until 2026, that will likely be different. With his trajectory, Gonzales could soon be seen as a trade headliner for a proven MLB veteran.
However, Gonzales should get a chance to go through Boston's minor league system and debut with the Red Sox. He has the type of power potential that you dream of. Right now, he looks good enough in the outfield. He'll likely become a first baseman in the long term (where he spent most of his time in the DSL in 2024).
Keep Gonzales and have a 40-plus home run type bat in your lineup for 15 years. The Sox haven't had a 40-homer season since J.D. Martinez in 2018.
David Sandlin
David Sandlin is someone who was heavily rumored to be involved in trades at the deadline. He needs to be put on the 40-man roster by the Rule 5 Draft, or he'll be available for selection, and he would undeniably be selected.
Sandlin was promoted to Triple-A right before the deadline, and his first start was fantastic (5 IP, 4 H, 1 R, 1 BB, 4 K). However, he might not impact the major league team as a starter immediately.
On August 5, Sandlin made his first-ever appearance out of the bullpen in a non-piggyback role. The right-handed pitcher allowed two runs on three hits over 1 1/3 innings. He struck out three batters and didn't walk any. It wasn't his best outing, but Sandlin showed good stuff and was regularly hitting 96-plus with his fastball. Coming out of the bullpen, Sandlin will be able to go all-out. He's shown he can get 100 MPH, and has great snap on his off-speed stuff.
Boston changing Sandlin's role paints a clear vision — it wants to get Sandlin in the bullpen for September/October baseball. Trading Sandlin could've potentially landed the Red Sox a reliever to help for the postseason push. But NOT trading Sandlin got them a reliever who could help for the postseason push and a prospect who could become a serious weapon as a starter or reliever for the foreseeable future.
Sandlin seems to be beloved by his teammates, makes an effort to connect with the fans, and throws filth on the mound. That's the type of player you want in your clubhouse.
Yhoiker Fajardo
Most of the reasons for keeping Gonzales could be applied to Yhoiker Fajardo. If the Red Sox traded Fajardo now, they would be selling at his lowest value.
Boston acquired Fajardo in an offseason trade with the Chicago White Sox for reliever Cam Booser. Fajardo is an 18-year-old right-handed pitcher with a 2.29 ERA (2.56 FIP), .210 BAA, and 1.04 WHIP in 13 appearances (11 starts) between the FCL and Single-A. He has 49 strikeouts compared to 15 walks in 51 innings (as of August 5).
Fajardo took a few outings to get comfortable in Single-A, but has gotten things going recently. In his previous three outings before August 2, he allowed just one run on 12 hits in 14 1/3 innings. However, he only struck out nine batters compared to five walks.
On August 2, Fajardo tossed a career-high 5 2/3 shutout innings. He allowed just one hit and no walks, while striking out a season-high eight batters.
Fajardo doesn't turn 19 until October 3. He has good off-speed stuff, and his fastball velocity has already taken a jump this year. The Venezuelan has a long way to go, but he has a legitimate chance to become a top-100 prospect quickly. He was a lottery pick when Boston traded for him. He'd still be considered a lottery pick now. Give it some time, and that will change.
Brandon Clarke
Brandon Clarke's name swirled around in trade rumors at the deadline — maybe not as much as others, but his name was involved. There were a lot of scouts reported at Greenville games that Clarke started. While that's not out of the norm for any game, there were apparently enough of them at Clarke's starts to be worthy of reports.
The left-handed pitcher, a 22-year-old, was a fifth-round pick in 2024 and has already impressed enough to be considered a top-100 prospect in baseball by many publications. Clarke flew through Single-A, but has hit a bit of a snag in High-A. He has an electric fastball that can hit 100 MPH, an overpowering slider, a long-breaking sweeper, and a good changeup.
However, he has struggled with command and consistency. Clarke has 57 strikeouts in 35 2/3 innings between Single-A and High-A. He's yet to give up a home run, and has only allowed one triple and two doubles. Clarke's walked 24 batters and hit 11 more, though. He hasn't gone more than 2 2/3 innings since he returned on June 26 from a month-long stint out of action due to a blister. In that time, Clarke has thrown 11 2/3 innings in six starts. He has 19 strikeouts but 15 walks and five HBP. The poor control has led to long innings, causing Clarke not to pitch deep into games.
Even with the struggles, Clarke has a 3.79 ERA, .119 BAA, and 1.09 WHIP in those 35 2/3 innings. He has electric stuff, but just needs to iron out the command.
Clarke is a massive "two spectrums" prospect. If he doesn't figure out the command, he might never been a legitimate major league arm. However, if he gets it under control, Clarke has ace potential.
The Red Sox could've sold relatively high on Clarke and probably gotten a good return. It's nice to see that they are rolling the dice with him, because it's not a 50/50. Clarke's talent is enough that the Red Sox are rolling with loaded dice.