Three teams in the 2026 MLB playoffs are still chasing something no one in their current bracket has ever done: win a World Series.
That alone makes this divisional round stand out. Nearly 40% of the remaining field is made up of clubs looking for their first championship, and the race to be first among them feels pretty clear. The Milwaukee Brewers, San Diego Padres and Tampa Bay Rays are all still alive, but they do not enter this stage with the same kind of title odds.
Start with the Brewers, because the case for them is the easiest to make. Milwaukee finished 2026 at 103-59 and comes in with the best record in baseball.
The franchise’s lone pennant came in 1982, when it was still in the American League, which gives the Brewers a strange little footnote: they could become the second team, alongside the Astros, to win pennants in both leagues. Houston did it after moving from the NL to the AL and later collected five AL pennants plus its first two World Series titles.
Milwaukee’s current run has been as steady as anything in the sport. This is its eighth playoff berth in nine seasons, and the club has now won the NL Central in six of the last nine years, including four straight.
That is a massive shift from the long stretches of nothing that came before. From that 1982 pennant through 2007, the Brewers didn’t reach the postseason at all.
They finally got back in 2008, reached the NLCS in 2011, then went through another six-season playoff drought.
The problem, of course, is what happens when October gets serious. These Brewers teams have had trouble clearing the final hurdles.
They’ve reached the NLCS twice in this stretch and lost both times. They’ve also been knocked out in the Wild Card round four times and in the NLDS once after a bye.
Last year, the Dodgers swept them out of the NLCS and outscored them 15-4 in the process. Even so, Milwaukee enters this postseason as the most dangerous title threat of the three.
The Padres are the most familiar name in this group, and their history is a long mix of breakthrough moments and hard stops. They finally popped in 1984, winning the NL West and then rallying from an 0-2 hole in the best-of-five NLCS against the Cubs to grab the pennant.
That run ended with a 4-1 loss to the Tigers in the World Series, but it remains a landmark season for the franchise. The Padres then went to the postseason in 1996 and were swept in the NLDS, got back to the World Series in 1998 and were swept by the Yankees, and added a pair of playoff trips in the 2000s without advancing.
More recently, San Diego has been in the mix often enough to matter. The Padres have made the postseason five times in the last seven years, though they’ve reached the NLCS only once in that span.
That came in 2022, when the Phillies beat them 4-1. They look strong again now, but the path is not exactly friendly.
Their immediate challenge is Milwaukee, which is the best team in this round, and the road beyond that could be even more demanding.
Tampa Bay sits in a different kind of place. The franchise was long a punchline as the Devil Rays before dropping “devil” ahead of the 2008 season and turning into a regular contender.
The Rays went from annual cellar dwellers in the AL East to making the playoffs in four of six seasons from 2008-13. After five straight years without a postseason berth, they then reeled off five in a row from 2019-23.
They missed the next two, but they are back now and finished with the best AL record this year.
There is also a neat little oddity with Tampa Bay’s playoff résumé: the Rays have never lost an ALCS. They’ve only been there twice, but they won both times and then lost in the World Series.
That pattern gives this run a pretty clear fork in the road. History suggests the Rays either go out in the ALDS or keep rolling all the way to the World Series, where they would likely be underdogs again.
Their previous World Series trips ended against the Phillies in 2008 and the Dodgers in 2020.
All three clubs have a real shot to make a run. But if you’re ranking who is best positioned to break through first, Milwaukee is the obvious No. 1.
In Other News...
Rays Open Yankees Series With One Huge Advantage Still Looming
The Rays get the first crack at the Yankees in Game 1 of their American League playoff series at Tropicana Field, with Drew Rasmussen taking the ball for Tampa Bay. It is a familiar postseason setup for the Rays, who will try to use their home field to set the tone early before the series shifts north for Game 3 at Yankee Stadium. The schedule keeps the first two games in St. Petersburg, with national coverage on TBS, truTV and Max.
New York still has not announced its Game 1 starter, which leaves one key piece of the matchup unresolved as the opener approaches. The bigger question for the Yankees, though, is Aaron Judge, whose status remains uncertain because of a calf injury. For a Rays club trying to control the series from the start, that uncertainty is the kind of advantage that can shape everything about the first game, even before the first pitch is thrown. [Read more 🡒]
Rays Get Key Help Back As Kevin Cash Faces Bigger ALDS Call
The Rays are getting some timely reinforcements as the American League Division Series opens, with Chandler Simpson, Tyler Wells and Garrett Cleavinger all finishing their final workouts and expected to be part of the clubs plans. Simpson has moved past right foot soreness and has taken part fully in recent scrimmages, while Wells and Cleavinger, both dealing with forearm tightness, have returned to the mound for bullpen work and appear likely to make the 26-man roster.
For Kevin Cash, the bigger question may be less about availability than deployment. He confirmed all three are ready, but the Rays are still sorting out how they want to map the pitching beyond Game 1, which leaves the most important decisions hanging as the series begins. In a short series, having bodies back matters, but how Cash lines up the rest of the staff could end up mattering even more. [Read more 🡒]
Rays Now Have A New ALDS Problem To Prepare For
Carlos Rodn sat out the Yankees Wild Card Series, but Tampa Bay still has to plan for him in the American League Division Series. Aaron Boone has already signaled that Rodn is in line for a role in the matchup, and the left-hander could surface as a starter in Game 3 or 4 if New York takes that route. He could also be deployed out of the bullpen earlier in the series, which gives the Yankees some flexibility and leaves the Rays trying to prepare for multiple possibilities.
That uncertainty is what makes Rodn such a tricky variable for Tampa Bay. He finished the regular season with strong numbers and already has a notable start against the Rays on his rsum, so this is not a name they can simply ignore while mapping out the series. Whether he opens a game or enters in relief, his presence adds another layer to a matchup that already figures to demand careful pitching decisions from both dugouts. [Read more 🡒]