Starters Get New Starts: Dustin May to Boston, Nestor Cortes to San Diego

In the flurry of action just minutes before the trade deadline, two postseason contenders made moves to reinforce their starting rotations with starters looking to regain their previous form before hitting free agency. The Red Sox traded prospects James Tibbs III and Zach Ehrhard to the Dodgers in return for Dustin May, while the Padres continued their deadline fusillade by acquiring Nestor Cortes, 18-year-old infield prospect Jorge Quintana and cash, sending Brandon Lockridge to the Brewers. The Brewers will cover roughly $2.4 million of the money still owed to Cortes, with the Padres covering the prorated minimum salary for the rest of the season.

Let’s start in Boston. ESPN’s Jeff Passan reported that the deal was going down, while FanSided’s Robert Murray and MassLive.com’s Christopher Smith reported the prospect return. The Red Sox could certainly use rotation help. They rank in the middle of the pack in both ERA and FIP, but once you separate out ace Garrett Crochet, things look much less rosy; Brayan Bello is the only other starter with an ERA below 3.80. Offseason deals for Walker Buehler, Patrick Sandoval, and Justin Wilson made it clear that the Red Sox are eager to find upside in pitchers who are still finding their way after a recent injury, and May certainly fits the bill.

With palpable Walugi energy, upper-90s velocity, and pitch movement seemingly designed in a lab for maximum GIF-ability, May has been tantalizing Dodgers fans with ace potential ever since his debut in 2019. Injuries, most notably Tommy John surgery in 2021 and flexor tendon surgery in 2023, have kept him from turning into the ace it was so easy to envision him becoming. From 2019 to 2023, he got into just 46 games, an average of 9.2 per season, running a combined 3.10 ERA and 3.77 FIP. Unfortunately, flexor tendon surgery ended May’s season early in 2023, then in July 2024, right as he was getting ready for a rehab assignment, May tore his esophagus in a freak accident while eating dinner. It was a major injury that required a six-month recovery.

Understandably, May hasn’t looked quite the same this season. His arm angle has fallen a long way, from 30 degrees in 2023 to 20 degrees this season. His fastball velocity is still above average, but it’s down to 95.6 mph. He looks even more like a sinker/slider guy than he used to, with big horizontal movement on his two fastballs and his sweeper, and the occasional cutter to bridge the gap. Over 18 starts and 19 appearances, he’s thrown 104 innings with a 4.85 ERA and 4.70 FIP. But as ever, it’s easy to imagine May looking like an ace in the near future.

Although May is now 27, he still has fewer than 300 big league innings on his arm. After the slow recovery of the esophagus injury, he hasn’t been ramped up for all that long. He could regain some of the velocity or command that he’s surrendered over the last few years. He could also just get more comfortable. “After the first [surgery], I never felt right,” he said back in February. “It never felt like I was ever in a good spot. After I got the second one, haven’t had a painful day of throwing since then, knock on wood.” One day, we’ll stop looking at May as a pitcher who has at least a chance of becoming the next big thing, but clearly, the Red Sox still see him that way on deadline day.

In exchange, the Dodgers got two outfield prospects in Tibbs and Ehrhard. Both players are 22-year-olds selected out of college in the 2024 draft, and both have hit well enough to find their way to Double-A this season. The left-handed-hitting Tibbs was San Francisco’s first-round pick. He came over in the Rafael Devers trade, and Eric Longenhagen ranked him 13th in the organization with a 45 Future Value when he wrote up the Red Sox prospects in June. Eric tagged him as a potential righty-masher who could turn into a regular right fielder if he improved either his defense or his platoon splits.

Ehrhard came in at 30th on the list, with a 40 FV. We have him listed at 5-foot-10, and Eric described him as a max-effort hitter whose approach led to a 170 wRC+ in Single-A but which might not hold up against higher levels of competition. “He’s a corner-only outfield defender,” wrote Eric, “with roughly average underlying contact and power metrics (though plus plate discipline), but a swing style that raises visual alarm.”

This is a steep price to pay, but if any team can afford to pay it, it’s the Red Sox. They already have more young outfielders than they know what to do with, and that’s before you consider higher-ranked prospects like Jhostynxon Garcia. Still, before we move on to the other deal, I would be remiss if I didn’t mention that Tibbs was arguably the biggest piece in the Devers deal. Ben Clemens pegged him as such at the time, banking on the potential of a special bat. This should probably color your opinion of the deal at least a little bit. Maybe the Red Sox weren’t as high on Tibbs as we might have assumed at the time, maybe they haven’t loved what they’ve seen, or maybe they were just a little less concerned about getting future value for Devers than we might have thought. Either way, they have now cashed that potential in for two months of Dustin May.

Next up, we have the Brewers and Padres, who could conceivably end up challenging each other in the National League Wild Card race, swinging a trade. Ken Rosenthal of The Athletic broke the deal, while Joel Sherman of the New York Post and Jeff Sanders of the San Diego Union-Tribune reported that Lockridge and Quintana, respectively, would be involved.

Cortes is in his final year of arbitration, and he only arrived in Milwaukee in December, in the Devin Williams trade. He made just two appearances with the Brewers before a flexor strain derailed his season. He hasn’t pitched in the majors since April 3. However, he started a rehab assignment at the beginning of July, and has a 1.00 ERA over four minor league starts and 18 innings pitched. He’s struck out 18 and walked three. He went over five innings in his last two starts, so he shouldn’t be far from contributing in the majors again. However, it’s worth noting that his four-seamer is averaging 89.7 mph in Triple-A. Cortes is one of the game’s true crafty lefties, and velocity has never been his calling card, but that would represent a significant drop-off not just from the 92.1 mph he averaged in 2024, but from the 90.4 mph he averaged in his two appearances before the injury.

With Quinn Priester in the fold, Brandon Woodruff back from injury and looking like his old self, and Jacob Misiorowski blowing everyone away, the Brewers wouldn’t have had much space for Cortes once he returned. The good news is that the Padres don’t need Cortes to be his old self. They just traded away two starters in Ryan Bergert and Stephen Kolek, and they’re looking to fill out the back of rotation. They’ve got stars like Dylan Cease, Nick Pivetta, and a returning Michael King for the playoffs. They could even look to have Cortes pitch out of the bullpen in the playoffs like the Yankees did last year. Imagine how fast Mason Miller’s 103 mph would look after an inning or two of Cortes’ 89-mph fastballs.

Eric Longenhagen and James Fegan ranked Quintana 13th in the Brewers organization back in May and put a 40+ FV on him. The Venezuelan-born infielder has put up unexceptional numbers so far, running a 110 wRC+ in the Dominican Summer League in 2024 and a 101 wRC+ in the Complex League so far this season. But he’s a switch-hitting infielder who still has a lot of development ahead of him. In May, Eric and James had his hit tool as a 20, with a future grade of 45. Here’s the full blurb:

Quintana’s profile has shifted pretty rapidly compared to when he signed. His amateur profile was that of a contact-oriented switch-hitting shortstop, one with a higher floor and perhaps lower variance. But in Arizona, he looks more like an exciting power projection infielder who might outgrow shortstop. Quintana is an angular 6-foot-2 or so, and he’s an explosive rotational athlete with plus bat speed. His swing has gorgeous low-ball loft, and while there’s risk that Quintana’s lever length and bat path will interact in a way that leaves him vulnerable to good velocity down the line, for now it’s fine to be enthused about his potential for rare lefty infield power. There’s a chance his frame matures in the Goldilocks Zone, where Quintana adds enough strength to have impact power but not so much as to effect his mobility at shortstop. Based on early 2025 looks in Arizona, those chances are remote, and we consider Quintana a likely future third baseman whose overall prospect value is similar to that of a high schooler who goes in the comp or early second round of a draft.

Lockridge started the season in San Diego, but he posted just a 50 wRC+ in 47 games and 95 PA sandwiched around a hamstring strain, and got sent down to Triple-A El Paso at the end of June. He’s put up solid offensive numbers in the minors, running a 113 wRC+ with the Yankees in 2023, then a 116 wRC+ with both the Yankees and the Padres in 2024, and a 111 wRC+ over 21 games in El Paso this season. But Lockridge likely won’t hit enough to earn his way in the majors, and he hasn’t found his way onto an organizational top prospects list here since 2022. In the sense that he’s an elite speedster, great defender, and not much of a power threat, he certainly fits on the Brewers like a glove. If there’s one place you’d expect a player to make the most of such a skill set, it’s Milwaukee.

In all, this is kind of what both of these teams do. A.J. Preller dealt two back-end starters in order to get a superstar closer in Mason Miller, and in Cortes and JP Sears, he’s already found two back-end starters to take their place. All it cost was an outfielder he didn’t have room for, and it also netted him a prospect. On the other side, the Brewers have once again succeeded in turning pitcher depth and development into a player who won’t hit for power, but may well have found the team that will provide him the best chance to contribute.

Editor’s Note: An earlier version of this article indicated that Jorge Quintana was going from San Diego to Milwaukee. It has been updated to correct that mistake.