Dustin May stands out as a perfect Hoyer style gamble for 2026

Dustin Riese · Senior Writer · 52 minutes ago

Say what you want about Jed Hoyer and his approach to free agency, but those are the hands he has been dealt. Yes, everyone would love this team to operate like the big-market team they are, but the bottom line is that Tom Ricketts won't allow that to happen until at least 2027, when he finds out whether a Salary Cap will be imposed.

Until then, Hoyer needs to work with the budget he is given, which often puts him in a tough spot when it comes to acquiring free agents. Knowing he has had to alter his approach to landing talent, one of the things Hoyer has done better than most is find reclamation projects on one-year deals and turn them into key components for this team.

You saw that a ton last season, as Matthew Boyd, Colin Rea, Drew Pomeranz, Caleb Thielbar, and Brad Keller were all signed to one-year deals as reclamation projects, and from all accounts, were seen as the Cubs' most consistent arms from start to finish. Boyd signed a two-year contract with one year remaining, while Rea was just reupped on a new deal that keeps him with the Cubs for another season.

The rest of them are officially on the free agent market looking for new homes, but there is a high likelihood that Keller winds up back in Chicago on a multi-year deal, which would be huge for the Cubs' pen.

Plenty of high-quality pitchers have been linked to the Cubs already, but unless they change their spending approach in free agency, will the Cubs pull the trigger and acquire one of these ace-caliber arms? Granted, they could trade for one, which is the most likely route, but look for Hoyer to once again go after someone on a low-risk, high-reward deal, and Dustin May is someone who falls into that category.

The now 28-year-old righty and former third-round pick by the Los Angeles Dodgers, May has had an up-and-down career filled with some early bright spots, but tons of late dark spots as injuries have really altered his career. There is no question that when healthy, May has the stuff to be a legitimate starter in this league, as evident during the 2020 and 2021 seasons when May went 4-2 with a 2.63 ERA across 15 combined starts.

Until this past season, May had never started more than 10 games, which he did in 2020. Injuries have hampered his career, limiting his overall production on the mound. This season saw May get healthy for the first time in his career, and even then, he still didn't pitch a full season, as he went on to start 23 games in 2025.

Eighteen of those came with the Dodgers before being traded to Boston late in the season, as he endured a struggling 7-11 season with a 4.96 ERA. That sends him to 19-20 for his career, but with a 3.86 ERA, May has continued to prove that if he is available to give you innings, he will, for the most part, keep his team in games.

There is no denying that 2025 was a struggle for May, as the 4.96 ERA was not only a career worst, but the 21.1% K, 9.6% BB, 9.2% barrel, and 44.5% hard contact rate were also career worsts. He tossed a career-high 132 innings, which is the lone positive, but with a fastball that decreased in velocity, you wonder if the innings total had something to do with it.

However, before this season, May flashed plenty of potential, and if you remember his pitch, he had some of the best stuff in the game. With a fastball that reaches 100 mph and a steady dose of lethal offspeed pitches, May was seen as one of the better strikeout pitchers in the game, who also produced an elite groundball rate of 49.9%.

The ground-ball rate alone is worth noting, as it plays well at Wrigley Field regardless of whether the wind is blowing in or out. Now that the 2025 season is behind him, May is looking for not only a new deal but also a new opportunity to prove his worth, as he may be forced to take a one-year flyer deal to get an opportunity.

If that is the case, it falls right into the Cubs' hands, which is what they like to do, and Hoyer and company are going to look into it. While the initial reports expect him to land a one-year, $15 million contract, don't be surprised to see him get less than that, as the $10-12 million range seems more likely.

Even at that, a one-year deal with a price tag like that for a pitcher who has shown elite stuff isn't a bad idea because of what can come from it. Should the struggles continue, you would not be tied into a long-term deal and could move on from May sooner rather than later. However, should he return to his pre-injury form and prove that he is back, May becomes someone you could build your rotation around, as he is still young enough to remain for several years.