Dutch Lion’s 2026 MLB Playoffs Preview
Another season is coming to an end. But this year, we’re really excited. This could be the year. Locally, we have the Chicago Cubs, the Milwaukee Brewers, AND the Chicago White Sox all in the postseason. It’s rare. How rare? I’m glad you asked.
This is only the fourth time in history that both the North Siders and the Southsiders have been in Baseball’s postseason at the same time. The other years were 1906, 2008, and 2020. In 1906 the “Hitless Wonders” White Sox beat the Cubs in the only Crosstown Classic World Series 4 games to 2.
Add in the Brewers, and we’re down for some major Midwest baseball hysteria. Milwaukee ALSO made the postseason in 2008 and 2020, so this isn’t the first time that these two cities separated by only 81 miles have caught postseason baseball fever at the same time. But in both of those years, all three teams had a hard time winning one game, much less one series. (Brewers 1-3 in 2008 and 0-2 in 2020; Cubs 0-3 and 0-2; Sox 1-3 and 1-2).
But now it’s 2026. And what’s different this time is the Milwaukee Brewers have the #1 overall seed, finishing with baseball’s best record (103-59). Milwaukee will get a bye in the first round as the National League’s #1 seed, while the Cubs and White Sox will need to best two out of three series.
American League Playoff Seeds
1. Tampa Bay Rays (98-64) – A.L. East Champion – BYE
2. Cleveland Indians/Guardians (85-77) – A.L. Central Champion – BYE
3. Houston Astros (81-81) – A.L. West Champion
4. New York Yankees (93-68) – A.L. Wild Card #1
5. Boston Red Sox (87-75) – A.L. Wild Card #2
6. Chicago White Sox (84-78) – A.L. Wild Card #3
Wild Card Round (Best-of-3) (All games at the home of the higher/better seed)
#3 Houston Astros (81-81) vs #6 Chicago White Sox (84-78) – Chicago never seems to win at Houston, at least not since the 2005 World Series, when Houston was in the National League. Since they switched leagues in 2013, the Astros have beaten the Sox head-to-head in most years (7-3-3, no series in COVID 2020). The last time the Sox won the season series was 2019, with other winning years being ’15 and ’17. The Astros won in all the other years (seven winning season series) since ’13. This year, Houston won five of seven contests, including three of four earlier this month in Houston. So it doesn’t look promising for Chicago. This Sox team is “ahead of schedule”, as they say. They are too young, too inexperienced to make waves. Right? PICK: Houston
#4 New York Yankees (93-68) vs #5 Boston Red Sox (87-75) – The best rivalry in Baseball resumes with another best-of-3 at Yankee Stadium. Last year, the Yankees won two games to one over Boston. The pitching matchups are intriguing, with Payton Tolle vs Cam Schlittler in Game 1, Sonny Gray vs Max Fried in Game 2, and Ranger Suarez vs Gerrit Cole in Game 3. Like all of these best-of-3’s, anything could happen. Anyone could win. It’s good and bad depending on your perspective. PICK: New York
ALDS (Best-of-5)
#1 Tampa Bay Rays vs #4 New York Yankees – Why are the Rays so good? I think this, and write this almost every year! Is it the home-field advantage in Tropicana Field? Who else plays in a weird dome on bouncy turf? The Rays had the best home record in Baseball at 55-26 (tied with Milwaukee). Can the Yankees overcome their nemesis? PICK: Tampa Bay
#2 Cleveland Indians/Guardians/should have gone with “Spiders” vs #3 Houston Astros – The Indians are hot lately. They seem to get hot every September, it’s kind of weird. They are often mediocre all season until the end, it seems. PICK: Cleveland
ALCS (Best-of-7)
#1 Tampa Bay vs #2 Cleveland – I don’t think we can deny the Rays anymore. They have an excellent all-around ballclub, led by starting pitchers Drew Rasmussen (16-5), Nick Martinez (15-6), and ???? In the lineup, they have Chandler Simpson, who led the league with 46 stolen bases. They have Junior Caminero (2nd in AL in HR, 3rd in RBI’s), Yandy Diaz (led the AL in hits), and Jonathan Aranda. PICK: Tampa Bay
National League Playoff Seeds
1. Milwaukee Brewers (103-59) – N.L. Central Champion – BYE
2. Los Angeles Dodgers (100-62) – N.L. West Champion – BYE
3. Atlanta Braves (94-68) – N.L. East Champion
4. San Diego Padres (91-71) – N.L. Wild Card #1
5. Chicago Cubs (89-73) – N.L. Wild Card #2
6. Philadelphia Phillies (88-74) – N.L. Wild Card #3
Wild Card Round (Best-of-3) (All games at the home of the higher/better seed)
#3 Atlanta (94-68) vs #6 Philadelphia (88-74) – These division rivals will meet for the fourth time in the NL Playoffs (1993 NLCS: Phillies won 4-2; 2022 NLDS: Phillies won 3-1; 2023 NLDS Phillies won 3-1). As you can see, the Phils have dominated in this format, winning all three prior head-to-head matchups. Will they do it again? You betcha! PICK: Philadelphia
#4 San Diego (91-71) vs #5 Chicago Cubs (89-73) – These National League contenders have met in the NL Playoffs previously, most notably in the historic 1984 NLCS, where the Cubs blew a two games to nothing advantage in the then-best-of-5 format. San Diego got on a roll at home in Jack Murphy Stadium and won the last three games to win the pennant and advance to the 1984 World Series. They rematched last season in the NLWC round as well, with the Cubs winning two games to one. We think the Padres are a really good team, with a really hot superstar in Fernando Tatis. PICK: San Diego
NLDS (Best-of-5)
#1 Milwaukee (103-59) vs #4 San Diego – Milwaukee’s starting pitcher Jacob Misiorowski had an historic season, pacing the Brewers with a 1.80 ERA, .157 opponent’s batting average, and 252 strikeouts. Those three categories were the best in the major leagues, which has only been done three times before, ever, in the history of baseball (1965 Sandy Koufax, 1979 J.R. Richard, and 1986 Mike Scott). PICK: Milwaukee
#2 Los Angeles Dodgers (100-62) vs #6 Philadelphia – The two-time defending champion Dodgers won 100 games yet again, but they seem vulnerable. Don’t they? Or is it just me? The main reason for my hunch is because all-world hitter/pitcher Shohei Ohtani has been injured much of this season. He won’t be pitching this postseason, and his hitting was just average this year, at least mediocre for him. He still put up some stats, and the rest of the Dodgers still have loads of talent, but it looks like their gas tank is running low on fuel. PICK: Philadelphia
NLCS (Best-of-7)
#1 Milwaukee vs #6 Philadelphia – The Brewers are like a mini-dynasty, winning a ton of games and making the playoffs seemingly every year, yet never winning a pennant over the last decade plus. Well, this is the year. Milwaukee is too good to overlook. They won 103 ballgames! They have it all, led by the amazing manager Pat Murphy. PICK: Milwaukee
2026 World Series (Best-of-7)
#1 Milwaukee Brewers vs #1 Tampa Bay Rays
Two small market teams will face off for the 2026 World’s Championship. This is the year. THIS will finally be Milwaukee’s time to shine. One of the only MLB franchises to have never won a Title, the Brewers will be this year’s Champion. Five MLB teams have never won it all, the Brewers, Seattle Mariners, Colorado Rockies, San Diego Padres, and the….. Tampa Bay Rays. Hmmm, that’s interesting. Three of the five are current playoff qualifiers, and both #1 seeds are never-winners. In my matchup scenario, we will definitely have a new winner.
In the end, the Milwaukee Brewers will show their dominance, giving their franchise a first ever baseball championship, and their city a second-ever baseball title (1957 Milwaukee Braves). This has been a LOOOOONG time in the making. I still remember the 1982 Brewers, who lost in the World Series to St. Louis back when the Brew Crew was in the American League. Harvey’s Wallbangers were the real deal back then, but they never got back. Now it’s up to the “Miz”, Brice Turang, Jackson Chourio, William Contreras, Jake Bauers, Christian Yelich, Kyle Harrison, Aaron Ashby, and Logan Henderson to win it all for the Brew City.
Congratulations to your 2026 World Series Champions, the Milwaukee Brewers!
