The Milwaukee Brewers are one of five teams without a World Series title, so after knocking on the door of the promised land for the past several seasons, one of their trade deadline maneuvers was to bring in a World Series champion, former Los Angeles Dodgers pitcher Dustin May. May hasn’t lived up to his sky-high potential, mostly as a result of injuries, but he should still be a helpful asset for the Brewers moving forward.
May will make his first start for Milwaukee at 2:10 p.m. ET, when the Brewers host the Pittsburgh Pirates in the final game of a four-game set that Milwaukee currently leads 2-1. Braxton Ashcraft will try to secure a split for the Pirates.
Let’s break down this divisional contest with some odds and lines at DraftKings Sportsbook.
Pittsburgh Pirates at Milwaukee Brewers Best Bets
- Milwaukee Brewers Moneyline (-124): I’ll trust a team that has gone 12-6 since the All-Star break over one that has gone 7-12, especially when the latter has been without two of its best hitters for a month. The pitching matchup isn’t that lopsided.
- Dustin May Head-to-Head Strikeouts (-127): When these two pitchers last faced off on May 21, Ashcraft actually recorded more strikeouts than May, but the Brewers’ starter has recorded more strikeouts in each of the last two games.
Pittsburgh Pirates at Milwaukee Brewers prediction, preview
Pittsburgh has the second-longest active playoff drought in baseball and has finished dead last in the NL Central in five of the past seven seasons, but by most measures, the 2026 season has represented impressive progress. The Pirates have stayed at or above .500 for most of the season, and only a rough start to the second half (a 7-12 mark so far) has brought them below that mark. They still have the fourth-best offense for the season as a whole, although they’ve had a really rough go of it since the Midsummer Classic, posting the league’s sixth-lowest OPS across that span. Two of their best hitters suffered long-term injuries, as Oneil Cruz has been out since the start of June with a hand fracture and rookie Konnor Griffin, who’d really been starting to hit his stride, sustained a tendon tear in his finger. Additionally, Pittsburgh has had the eighth-worst pitching staff since the All-Star break, with 2025 Cy Young Award winner Paul Skenes struggling through a disappointing season, though at least its relievers have been sharp as of late. The Pirates also added to their bullpen at the trade deadline, acquiring Lake Bachar, Camilo Doval, and Kirby Yates.
With Los Angeles floundering on a six-game losing streak, Milwaukee suddenly has the upper hand on securing home-field advantage for a potential future League Championship Series. The Brewers have kept winning since the All-Star break, going 12-6, and, per FanGraphs, the Dodgers would be just two-to-one favorites in the LCS. Milwaukee’s offense has been the seventh-best in baseball for the season as a whole, and it’s mostly kept up that form through the All-Star break. Brice Turang, Jake Bauers, and Jackson Chourio have all been among the better hitters at their respective positions, even though Chourio has slumped somewhat since the Midsummer Classic. The Brewers have mostly won through their pitching, as only the New York Yankees have had a better combined staff ERA this season, and a top three of Jacob Misiorowski, Kyle Harrison, and Logan Henderson is a scary proposition for the rest of the league in the playoffs. Additionally, Milwaukee’s bullpen has been baseball’s fourth-best, as Trevor Megill and Abner Uribe have given up just two combined runs over the last two months. The Brewers had a relatively quiet trade deadline, acquiring May and Colorado Rockies reliever Antonio Senzatela, but they didn’t need to do too much.
Ashcraft has been solid, even if inconsistent, this season. He had a 2.77 ERA through the end of May but hasn’t been as good since, pitching to a 5.64 mark and allowing 16 runs in 14.0 innings across a three-start stretch in July. Still, for the season as a whole, he’s allowed two or fewer earned runs in 15 of his 22 appearances, and advanced numbers suggest he’s been pretty sharp, as he ranks in the 74th percentile in expected ERA. In particular, Ashcraft has displayed an impressive mix of power and control, sitting in the top quartile in both strikeout and walk rate, and against a team that’s walked the second-most times and struck out the 12th-fewest, that could be pivotal. Ashcraft has also induced chases at a 97th-percentile rate, and Milwaukee has baseball’s most disciplined plate approach. He is occasionally prone to significant damage, ranking in just the 27th percentile in average exit velocity (a stat in which the Brewers rank ninth), but provided he can continue to do a good job forcing grounders, he has a decent chance of stifling Milwaukee. Ashcraft has been slightly worse on the road and the Brewers somewhat better at home, but he faced Milwaukee at this venue as a rookie and held it scoreless over three innings on two days’ rest.
He should have the slight edge in the starting pitching matchup over May, who’s pitched to a 4.38 ERA this season. May has had plenty of highs, including a one-hit shutout on June 15 and a combined 11 innings of one-run ball over his last two starts, but he’s also had his fair share of stinkers, including a five-run, two-out effort against the Atlanta Braves on July 2. His advanced profile is mixed; although he ranks above the league median in expected ERA, he hasn’t done a very good job inducing whiffs, which could help mitigate one of Pittsburgh’s biggest weaknesses. Furthermore, May has been rather prone to hard contact, ranking in the fourth percentile in hard-hit rate and the 18th percentile in average exit velocity, and although Cruz’s and Griffin’s injuries take some of the juice out of the Pirates’ lineup, they’ve still produced hard hits at an above-average clip. Location splits aren’t that helpful, given that May has only made two career starts at American Family Field, but it’s worth noting that he’s recorded a 2.08 ERA in those starts and that Pittsburgh’s OPS is nearly 100 points worse on the road.
Pittsburgh Pirates at Milwaukee Brewers pick, best bet
Best Bet: Milwaukee Brewers Moneyline (-124)
Even though advanced stats slightly prefer Ashcraft to May overall, the Brewers’ offense is in much better form than the Pirates’, especially given Pittsburgh’s struggles on the road. The hosts also have a far better bullpen.
Strong Lean: Dustin May Head-to-Head Strikeouts (-127)
Even though May doesn’t induce a lot of whiffs, he still has a respectable 51st-percentile strikeout rate, and the Pirates have been fanned 18 more times this season than any other team.
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