As the MLB trade deadline approaches, Dustin May finds himself at the center of swirling rumors and mounting pressure. The 27-year-old Dodgers right-hander, plagued by injuries and inconsistent performances, is now a prime trade candidate. His recent struggles against the Red Sox only intensified speculation, with the Yankees emerging as front-runners to acquire him.

The Dodgers face a critical decision: trade May for immediate help or risk losing him as he enters free agency. With Blake Snell’s return looming, May’s role in the rotation is uncertain, and his value—despite his injury history—could net a significant return. Whether Los Angeles opts for a star pitcher or top prospects, the clock is ticking.

Could Dustin May’s Injury History and Trade Buzz Push the Dodgers to Deal Him for a Star Pitcher or Yankees’ Top Prospect Before Deadline?

Is Dustin May’s latest Red Sox meltdown the final straw for Dodgers?

Dustin May’s recent performance against the Boston Red Sox raised serious questions about his future with the Los Angeles Dodgers. In his July 27 start at Fenway Park, May blew a 3-1 lead in the fifth inning, surrendering an RBI triple to Roman Anthony and a go-ahead two-run homer to Alex Bregman. He finished with four runs allowed in five innings, continuing a pattern of inconsistent outings.

The timing couldn’t be worse, as trade rumors have intensified around the 27-year-old right-hander. With multiple years of team control remaining and undeniable raw talent, May represents one of the Dodgers’ most valuable trade chips if they decide to bolster their roster before the deadline.

Why keep May when they could upgrade?

The Dodgers have been actively shopping for pitching help, and May’s uneven performances make him expendable despite his potential. His 4.12 ERA and 1.28 WHIP through 18 starts hardly scream “untouchable,” especially for a team with World Series aspirations.

The Dodgers face a classic dilemma here – sell high on May’s potential now or risk watching him blossom elsewhere while getting nothing in return.

But he’s shown flashes of brilliance! That filthy two-seamer could be an ace-maker if he stays healthy.

Health is the operative word, Tomato. His Tommy John history makes him far from a sure thing.

Will the Yankees really trade their top prospects for an injured-prone starter?

Reports indicate the New York Yankees have emerged as front-runners in the Dustin May sweepstakes. The Bronx Bombers, desperate for rotation help behind Gerrit Cole, might be willing to part with premium prospects to acquire May. Names like outfielders Spencer Jones and Jasson Domínguez have surfaced in preliminary discussions.

However, surrendering elite young talent for a pitcher with May’s medical history represents significant risk. Since debuting in 2019, May has made just 50 starts due to various injuries, most notably Tommy John surgery in 2021 that cost him nearly two full seasons.

Trade package projections

Industry insiders speculate the Dodgers could demand:

• A Top 100 prospect (OF Spencer Jones or SS Roderick Arias)
• A MLB-ready bullpen arm (RHPs Clayton Beeter or Greg Weissert)
• A lottery ticket lower-level prospect

That seems like an overpay for May given his inconsistent performance!

Remember what the Yankees gave up for Jameson Taillon? Teams pay premiums for controllable starting pitching at the deadline.

What star pitchers could Dodgers target if they flip May?

If Los Angeles parts with May, they’ll likely redirect him toward acquiring established rotation help. Possible targets include:

Keller presents particular intrigue. The Pirates righty owns a 3.53 ERA and 3.42 FIP this season, though some metrics suggest he’s been fortunate. His command improvement (2.1 BB/9) would fit perfectly in LA’s pitch-to-contact approach.

Could a three-team trade solve everyone’s problems?

With multiple clubs involved in May discussions, a complex multi-team swap could maximize value for all parties. One theoretical framework:

• Dodgers receive: SP Mitch Keller from PIT
• Pirates receive: INF/OF prospects from NYY
• Yankees receive: SP Dustin May from LAD

Such a deal would let Pittsburgh stockpile young position players while the Yankees and Dodgers address immediate rotation needs. The Pirates have employed similar strategies in recent trades involving Joe Musgrove and Tyler Glasnow.

Wouldn’t the Pirates just trade directly with the Yankees then?

Not necessarily – the Dodgers’ system has better middle infield depth, which Pittsburgh covets. Three-team deals create more matching opportunities.

When is the absolute latest the Dodgers can wait to trade May?

The MLB trade deadline falls on August 1 at 6 p.m. ET this season. However, Dodgers decision-makers likely won’t wait until the final moments. Several factors could accelerate their timeline:

• Competing suitors making offers for similar pitchers
• Potential injuries to their own rotation
• May’s scheduled starts before the deadline

The next 48 hours could prove decisive, as teams finalize evaluations and adjust their trade boards. May’s situation encapsulates baseball’s eternal risk-reward calculus at the deadline – do you bet on upside or established production?

My prediction? Dodgers trade May in a three-team deal that nets them Keller and a bullpen piece, while keeping their top prospects intact.