Memorial Day Significance
Memorial Day serves as an important benchmark in the regular season, marking the time when we should ideally have gathered enough insights to assess all 30 teams.
Current Uncertainties
However, as we approach 2026, it feels like unexpected twists could still arise, indicating that we still require additional data. Fortunately, several teams with unresolved questions are set to compete against each other in the upcoming week. Be sure to check back on June 1; we’re confident our assessments will be ready by then.
Key Series to Watch (Week of May 25)
Cubs vs. Pirates
3 games (Monday-Wednesday)
Head-to-head: Last year, the Cubs dominated the Pirates with a 10-3 record, outscoring them 54-26. However, they faced an unexpected challenge when they played against a significantly improved rival in April, losing the first series of 2026 two games to one, managing to salvage a win only after a comeback in the finale.
Storyline: It’s a pivotal moment for both teams. The Cubs, who previously had two 10-game winning streaks this season, are now grappling with an eight-game losing streak, having lost 12 of their last 14. Meanwhile, the Pirates have had a rollercoaster ride, struggling to maintain momentum after briefly getting above .500. With both teams showcasing considerable talent, one might break free from their slump in this matchup.
Watch out for: Konnor Griffin is not the only promising Pirate; Spencer Horwitz is also shining, hitting a leadoff home run against Dylan Cease on Sunday and enjoying a .306/.405/.516 (.921 OPS) performance in May.
Cardinals vs. Brewers
3 games (Monday-Wednesday)
Head-to-head: The Brewers and Cardinals split their earlier matchup this season, each winning a game before a rainout. The Brewers narrowly won the 2025 season series, 7-6.
Storyline: To stay competitive in the NL Central, keeping close tabs on this series is crucial. The Brewers currently lead but have only a 4.5-game margin over the last-place Pirates. The Cardinals, in second place, trail by just a game and a half, meaning this series could be a real litmus test for their contention plans.
Watch out for: The Brewers have seemingly come out on top in the Rafael Devers trade, particularly with Kyle Harrison’s impressive performance (nine starts, 1.77 ERA, 11.6 K/9). He is set to pitch against the Cardinals’ Michael McGreevy, who has a commendable 2.40 ERA in his ten starts.
Twins vs. White Sox
4 games (Monday-Thursday)
Head-to-head: After a dominant performance against the struggling 2024 White Sox (12-1), the Twins lost the 2025 season series, 5-8. This matchup marks their first face-off in 2026.
Storyline: The White Sox are currently hovering around .500, sitting second in the AL Central, which is quite a turnaround from their previous three seasons of heavy losses. The Twins, having improved as well, are just half a game behind. This series will be significant in determining who makes a stronger case for redemption.
Watch out for: Byron Buxton appears to be back in form, hitting .281 with eight home runs and 15 RBIs in May, contributing to the Twins’ recent success, having won six of their last seven games.
Yankees vs. Athletics
3 games (Friday-Sunday)
Head-to-head: The A’s secured a 2-1 victory in their first matchup against the Yankees this season back in April. Now, they aim for a win at home to end a streak of not winning or splitting the season series against the Yankees since 2019.
Storyline: Both teams need to step up their game. The A’s lead the AL West but are just above .500, relying heavily on a strong offense but needing improvements in their pitching. Conversely, the Yankees have struggled recently, averaging three runs per game in their last stretch, raising concerns about their standings.
Watch out for: Nick Kurtz is showing no signs of slowing down, boasting a .350/.480/.563 (1.043 OPS) with 22 RBIs this month, aiming to shake off any potential sophomore slump.
Phillies vs. Dodgers
3 games (Friday-Sunday)
Head-to-head: These teams last faced off in the 2025 NLDS, which the Dodgers won. However, in regular season matchups, the Phillies have been strong, holding a 9-3 record against the Dodgers since 2024.
Storyline: The recent postseason matchup feels distant as the Phillies have been on a wild ride in 2026, currently performing well under former Dodgers manager Don Mattingly. While their record is near .500, their recent homestand saw them struggle, hitting a collective .201 since May 11, which they need to improve as they face strong Dodger pitching.
Watch out for: Teoscar Hernández has stepped up, hitting .383 with four doubles, three home runs, and 14 RBIs in the last 13 games, helping to boost the Dodgers’ offensive output.
