As the trade deadline approaches, the Brewers face the Chicago Cubs for a series that could influence the outcome the fate of Chicago’s season.

The Cubs sit last in the division, but still within reach of a Wild Card spot. Given the crowded competition for those final playoff spots, this series could ultimately cause the Cubs to sit out of major additions if the Brewers take a commanding series victory.

It’s an opportunity to capitalize on a disappointing opponent, but the Cubs have been playing better lately. That’s part of what drives the narrative home for this potentially playing a role in the Cubs’ deadline plans. Over the past 30 days entering Sunday, according to FanGraphs, the Cubs rank 18th in runs scored and sixth in team ERA. That pitching performance could prove vital to how this three-game set plays out.

Although the Cubs have been hovering around the middle of the pack offensively, Ian Happ is a key performer who has stepped up recently. After a slog of underperformance, Happ has bounced back with a .261/.376/.543 (156 wRC+) slash line that includes 12 doubles and nine home runs since June 1.

Probable Pitcher Matchups

Monday, July 22 @ 7:05 p.m: Tobias Myers (3.13 ERA, 4.16 FIP) vs. Javier Assad (3.27 ERA, 4.51 FIP)

This series has quite a few pitchers starting with ERAs significantly lower than their underlying peripherals suggest, but this could prove to be one of the more fascinating matchups of the week. Tobias Myers’ 3.13 ERA has been vital to the Brewers’ success. His most recent performance was one of his most impressive, an eight-inning shutout against the Pirates. As the season has progressed, he’s been walking fewer batters, giving up fewer home runs, and inducing more groundballs. Will that formula carry over against this Cubs lineup?

Javier Assad hasn’t been the most convincing pitcher, especially in recent weeks. After a solid start to the season, Assad had a 1.49 ERA after nine starts. In eight starts since then, Assad’s 5.59 ERA has been accompanied by a rising walk rate and a growing tally of home runs allowed. He usually doesn’t go deep in games, only pitching at least five innings in four of those nine recent starts.

Tuesday, July 23 @ 7:05 p.m: Colin Rea (3.77 ERA, 4.48 FIP) vs. Jameson Taillon (3.10 ERA, 3.81 FIP)

Colin Rea has been a steady presence for the Brewers this season, working a 9-3 record and a 3.77 ERA. There have been a few unsightly pitching lines, but in his eight most recent starts, he has allowed more than two runs just twice. That’s a model of consistency the Brewers are grateful for as Rea has even tapped into some more strikeouts lately. He doesn’t give away many free passes and he’s done a great job of forcing groundballs, feeding into the team’s defensive strength.

Jameson Taillon might not be an ace, but he’s a practical, effective pitcher when he’s at his best. He has a 3.10 ERA this season, which would be the best mark of his career. Taillon has expertly limited hard contact this season. His 35.6% hard-hit rate is in the 74th percentile, according to BaseballSavant. Taillon made significant improvements to his cutter, his second-most used pitch. The pitch allowed a .521 SLG last year, compared to .267 in 2024.

Wednesday, July 24 @ 1:20 p.m: TBD vs. Justin Steele (3.07 ERA, 3.18 FIP)

Joe Ross hasn’t pitched for the Brewers since May 20, but this could be the time for his return as he wraps up a rehab assignment. Although he isn’t the flashiest pitcher, he had been on a solid run before his injury. In his last four games, he had a 3.18 ERA over 17 innings. Ross had made one appearance this year against the Cubs, going six innings while allowing one run on May 3.

Justin Steele’s 2-4 record is deceptive given his actual performance. Over a nine-game span from May 27 to July 11, Steele pitched to an impressive 1.48 ERA. His most recent start, however, was much less dominant. In 4 ²⁄₃ innings against the Diamondbacks, he allowed five runs. Steele generally doesn’t give up many home runs or even surrender much hard contact, so it will be an important test in the series finale for the Brewers to face one of last year’s Cy Young candidates.

Prediction

The Cubs are at the bottom of the division for a reason. Although they aren’t quite in the “bad” category, they haven’t been the most impressive of the Brewers’ NL Central rivals. Still, they’ve been much better lately. I have more faith in the Brewers offense, but the Cubs bullpen has been the best in baseball over the last 30 days with a 1.86 ERA. If Milwaukee’s offense can’t create many leads, it could lead to a coin flip of a series. With that said, I think the overall quality of Milwaukee’s team is slightly higher, leading to a 2-1 series victory.