There are as many as 22 games remaining if a team goes to the World Series, and the distance in every series, to end the 2026 season.
If you don’t tune into playoff baseball, you’re missing out. A lot of people, myself included, praise the NHL for having a great postseason, but baseball might be just as good. There are more pitching decisions and matchups, and the importance of every pitch is magnified. We have four series starting today and I think we can put some wagers on the full games.
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Houston Astros’ Yordan Alvarez celebrates after hitting a two-run home run during the first inning against the Kansas City Royals in Kansas City, Mo., on June 12, 2026. (Charlie Riedel/AP)
White Sox vs. Astros
This might be the poster year for why baseball should change the postseason format. We have the Astros barely making the playoffs with a .500 record, and they get to host a series, while the White Sox, who finished three games ahead of the Astros, have to travel to Houston to play them. The Astros have the experience and a potential MVP in Yordan Alvarez. Their offense is almost certainly better than the White Sox. In terms of pitching matchups, I think it is fairly close. This will come down to whichever team is less likely to make a mistake. The Astros are 5-2 against the White Sox this year. I think the White Sox, even with their inexperience, are in a better spot to win the series. The Astros have shown they are an average team all year long. I like the White Sox to win, and I like this series to go 3 games.
New York Yankees starting pitcher Max Fried delivers during the sixth inning of a baseball game against the Pittsburgh Pirates in Pittsburgh, Friday, April 4, 2025. (AP Photo/Gene J. Puskar)
PHILLIES AVOID COLLAPSE, ASTROS SNEAK IN AS MLB POSTSEASON IS SET
Yankees vs. Red Sox
Another chapter in the storied histories of these two clubs. The Red Sox have been one of the hottest teams in baseball for the past few months. The Yankees have been consistent all season. Offensively, the series may hinge on how well Ben Rice will do. Aaron Judge is unlikely to play in the series, but New York has played well without him. The Red Sox seem to have a bit more of a balanced offense. I think the pitching edge comes on the Yankees side. They have the likely Cy Young winner going in Game 1, then they can send out Max Fried, and finally Gerrit Cole for their three starters. The Red Sox have a team ERA about the same as the Yankees, but Sonny Gray is really the only guy I consistently trust. I like the Yankees, but I won’t personally play the -170 on them.
Atlanta Braves starting pitcher Chris Sale pitches during the second inning against the Los Angeles Angels in Anaheim, California, on April 6, 2026. (Caroline Brehman/AP Photo)
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Braves vs. Phillies
The Atlanta Braves host the Philadelphia Phillies, and this is a very similar series to the Yankees and Red Sox. The Braves were consistent all year, and the Phillies showed stretches of being great and others where they were a little less impressive. Philadelphia has the rotation, but because of how this season went for them, I would guess they have to start Jesus Luzardo first, but he pitched in relief yesterday. Ideally, they send Christopher Sanchez, then Zack Wheeler, and then Luzardo if needed.
Because they needed to fight for their spot until the last day of the season, it likely won’t line up that way. The Braves only really have Chris Sale and should win the first game. I just don’t know if they will close out the series. I’d lean to them since they have home-field advantage and likely will take the opener. I really need to see how the Philadelphia rotation aligns before wagering on it.
Mason Miller of the San Diego Padres pitches during Game Two of the National League Wild Card Series between the San Diego Padres and the Chicago Cubs at Wrigley Field on Wednesday, Oct. 1, 2025 in Chicago, Illinois. (Mary DeCicco/MLB Photos via Getty Images)
Padres vs. Cubs
I’m taking the Padres, and I’m taking over 2.5 games in this one. Simply put, the Cubs don’t have the pitching staff to advance. Their starters have been rocked all year and continue to give up long ball after long ball. The offense has carried them, but as pitching gets tougher, it will be harder for them to score and be successful. Their defense could make a difference, but I just don’t see it happening. The Padres have the better rotation, a lockdown closer, and have been playing great baseball over the past few months. I’m a Cubs fan, but I don’t see it happening for them. Give me the Padres and a three-game series.
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