Milwaukee Brewers (1) at Los Angeles Dodgers (2), 8:00 PM ET

MIL: RHP Dustin May (7-9, 4.70 ERA, 97 DRA-)
LAD: RHP Tyler Glasnow (5-2, 3.53 ERA, 79 DRA-)

Dustin May was at one time one of the Dodgers’ most prized young players—a young ace with devastating, wiffleball-worthy stuff and an equally jaw-dropping set of long, curly red hair—who looked set to anchor their rotation for the next decade. But sadly, as we all know by now, May suffered one injury after another and never really got the chance to be what he could’ve been in L.A. With his velocity down to average-ish levels following his return from Tommy John surgery, the Dodgers eventually gave up on him. May has now pitched for four different teams over the last two seasons and really struggled to prevent runs. In a way, he looks as if stuck at a crossroads.

Perhaps the most shocking fact about May is that he’s barely 29 years old and that, despite making his debut at age 21, he’s only pitched 469 ⅔ innings in the majors. That’s after 145 ⅔ of those came this season, when May made 30-plus starts in a calendar year for the first time in his pro career. And while his ERA wasn’t pretty, good news: his peripherals and stuff are much improved! May has regained most—albeit not all—of his former velocity; he now sits 97 mph and can make it tail or carry at will. He also has his usual cutter, which he favors against lefties, and his breaking pitches have always been amongst the most visually appealing in the sport.

On paper, then, May has frontline-starter stuff. In practice, however, the operation just doesn’t generate those kinds of results. His breaking pitches have always been oddly terrible at generating chases and misses—maybe they move so much that batters can see them out of his hand. His whiff and chase rates are firmly mediocre, and he tends to get hit fairly hard. In a sense, May is the ultimate “how can this guy not be good?” starting pitcher in baseball. (A title which used to belong to Nick Pivetta, and could be seen as a comfort to May—in 2030.) But he’s going to keep getting opportunities as long as his stuff is as theoretically good as it is. And he should.

Glasnow, meanwhile, has settled into his role as the most overqualified fourth starter in baseball. He was effectively wild in the NLDS clincher, allowing only a single hit but walking five in 4 ⅔ frames. Dave Roberts has shown in the past that he’s comfortable with Glasnow facing the order three times in a playoff setting, but with the Dodgers having fallen behind in the series and a potential Tarik Skubal start directly following Glasnow, I would expect a shorter leash than usual.

Still, this is far from an opener situation; the chances of Glasnow not clearly outlasting May in this game are very slim outside of a huge collapse. Glasnow’s plan of attack is remarkably consistent at this point: fastballs and curveballs to lefties, a more complete mix to righties. The fastballs, both the four- and two-seam, will be in the zone (at least in theory), whereas the curveball will be the chase pitch. The slider’s role depends on Glasnow’s feel that day.

It’s been a while since Glasnow got consistent whiffs with his fastball. Even though his command has improved as he’s aged, he’s very much a control-over-command pitcher, and the former can waver at times. He makes for a really fascinating matchup with Milwaukee’s pesky and disciplined lineup—if his command is working, he has the stuff to tame them, but if he can’t find the zone and becomes predictable, there’s a good chance that Milwaukee extracts at least 20 pitches per inning out of him. Glasnow is also famously bad at holding runners, and the Brewers have shown a willingness to be aggressive on the bases. Walks could be double trouble for the Dodgers if they come.

There’s some vague long-term storytelling going on with this pitching matchup that could make it a poetic matchup of grandiose proportions, if you’re willing to squint a little. It’s not everyday that a former savior has a chance to bury those who once cheered him on, and that said former savior is facing off against his successor. Glasnow has essentially filled May’s role in the Dodgers’ plans since his arrival in 2024—in another universe, maybe they would be starting back-to-back playoff games. In this universe, however, May will not get a chance to write his own epic tale against his former club. (His first postseason “start” consisted of 14 batters and 51 pitches.) Instead, he’ll be the first in a long line of arms trying to deliver the coup de grâce. Glasnow’s tale will be more classic in shape, but don’t expect Dave Roberts to keep his leash too loose, especially after the seventh inning last night.