Paul Toboni pulls off his first trade with his former team — the Boston Red Sox
They say to never make a trade for the sake of making a trade. But they also say that trades are best judged in hindsight. As we began the 100-day countdown to Opening Day at Wrigley Field in Chicago, news broke of a trade. Last night, Paul Toboni traded with his former boss, Craig Breslow, in a 1-for-1 trade of promising minor league pitchers. The Washington Nationals acquired fireballer right-handed pitcher Luis Perales for left-handed pitcher Jake Bennett.
Both pitchers are Tommy John survivors as they make their way back from surgeries on the UCL in their pitching elbows. That’s something they both have in common. They have both been highly ranked in their respective farm systems. Right after the trade, MLB Pipeline placed Perales at №5 in the Nats system for prospects, and Bennett at №7 in a deeper Red Sox farm system. Oddly, after the trade, evaluators seemingly bumped Bennett up.
Perales, 22, was the №5 prospect in Boston’s system, according to Baseball America, and its №7 prospect according to MLBPipeline.com and as mentioned moved up two spots in the re-rankings after the trade.
On the Top-100 rankings in baseball, Perales was the №57 prospect in baseball in 2024 — according to Baseball America — before undergoing Tommy John surgery in June of that season, and then fell off the list.
The newly acquired Perales was named by Baseball America as having the “best fastball” in Boston’s minor league system prior to both the 2023 and 2024 seasons. Perales returned to the mound in 2025, appearing in three games (2.1 IP) between Double-A Portland and Triple-A Worcester.
In this trade, Breslow and former Red Sox executive, Toboni, both know Perales. But how well did Toboni know Bennett? The book on Perales is that he has a 70-rated fastball on the 80-scale — but only 40 on the control per MLB Pipeline. That is the concerning part. This is where some evaluators see what they call reliever risk. And maybe that is a risk that Toboni was willing to take.
In early 2023, Bennett got the task in Single-A to face a Delmarva team stacked with top prospects including Jackson Holliday. It was that classic lefty-on-lefty matchup. Holliday was the №1 draft pick in the previous year, and got the call from the ump on a 3-2 pitch that froze Holliday in the batter’s box. While it should have been a strikeout, that’s why the ump works Single-A games. Holliday called Bennett one of the toughest pitchers he faced. Bennet was dominant in 2023. Unfortunately his 2024 season would end abruptly due to TJ surgery. The Nats worked him back in 2025 and he finished in Double-A, with an impressive 2.27 ERA across all levels.
After the season, Bennett pitched in the thin air in the Arizona Fall League as did Perales. They faced each other to start a game on November 1. How do you like that for coincidences? Bennett shined and Perales whined. It was like two pitchers going in different directions in that game — just a small sample size and one to forget if you were Perales. Nats’ 2025 draftee Ethan Petry lined a hard single off of Perales in that game. While Bennett led starters with 25 strikeouts in the AFL, Perales had an incredible 15.1 K rate but faltered with a 10.32 ERA in his six short starts. What got Perales was wild control and 11 walks in his 11⅓ innings of work — and there you have what is troubling about Perales — control.
With this, you know why some Nats’ fans will have flashbacks to the former administration’s love for high octane pitchers like Henry Rodriguez and later, Tanner Rainey, as pitchers with 100 mph fastballs and no idea where the ball was going. You hope that Toboni would never make that type of move and trusts Perales will get the control back.
Perales ranked 15th in all of Minor League Baseball (min. 30.0 IP) with 14.97 strikeouts per 9.0 innings in 2024. He went 2–2 with a 2.94 ERA (11 ER/33.2 IP) and 56 strikeouts in nine games (nine starts) in 2024 prior to the injury. Perales pitched to a 1.88 ERA (6 ER/28.2 IP) with 49 strikeouts and just 10 walks in in his final seven starts after allowing five earned runs in 5.0 innings across his first two starts of the season.
Through five professional seasons (2021–25), Perales has posted 12.56 strikeouts per 9.0 innings and 0.7 home runs per 9.0 innings. He’s surrendered just 12 home runs in 163.1 innings pitched. He is 6–11 with a 3.31 ERA, 228 strikeouts and a .217 opponents’ batting average in 47 professional games (43 starts). A native of Guacara, Venezuela, Perales signed with Boston as an international free agent on July 2, 2019 for just $75,000.
This is really the type of trade you just don’t see in baseball anymore. A 1-for-1 trade that Keith Law of The Athletic called a “challenge trade” which Law explained is a trade that occurs when two players, same position, are traded for each other in a one-for-one deal — “where it seems like this sort of thing just isn’t done anymore.”
“If you’re looking for me to name a winner in this deal, sorry, I’m not going to do so. The Red Sox are trying to contend right now, and they have a clear core competence in helping pitchers who can throw strikes improve their stuff. The Nats are years from contention, and while Bennett would probably have made 20 starts for them in 2026, he doesn’t have the pure upside of a Perales — and upside is what Washington should be targeting in every deal.”
— Keith Law wrote for The Athletic
“Toboni walked into a system with a lot of raw talent, maybe some of it underdeveloped to date, and the more he can add to that while also revamping some of their player development processes, the faster the rebuild will go. The trade just makes sense for both sides, period.”
For those who are trying to rationalize why Toboni made this trade they explain that Boston is already a contender and Perales only has one minor league option season remaining (Nats could and should request an extra option for loss of time due to injury) compared to Bennett with his three options. Could this be that Toboni was willing to take the higher risk because he wanted the higher ceiling pitcher? Another factor could be age. Perales is nearly 2⅓ years younger and fits this prospect profile of going younger.
And everyone will have their opinion about this trade in the hours and days after the trade. Again, these trades are best judged years down the road, but Law first says that he won’t name in a winner in this trade then he goes on to say that the trade makes sense for both sides. Well, there’s one opinion.
