One of the many interesting nuggets regarding the divisional round of the 2026 Major League Baseball playoffs is that nearly 40% of the remaining field is comprised of teams shooting for their first-ever World Series title. 

Many die-hard baseball fans are familiar with the trivia question that asks which five have never won it all. There’s only one team that hasn’t played in the World Series, the Seattle Mariners, and it got one win away last year. The Colorado Rockies have won a pennant but never won the World Series. 

The other three who haven’t won it all are the Milwaukee Brewers, San Diego Padres and Tampa Bay Rays. They’re all still in 2026, but who is most likely to win it all? Let’s rank them. 

3. San Diego Padres

• 2026 record: 91-71
• Odds to win World Series (via DraftKings): +1100
• Pennants: 1984, 1998

The Padres were a downtrodden franchise until finally breaking through in 1984 by winning the NL West and coming back from an 0-2 deficit in a best-of-five NLCS against the Cubs to win the pennant. They lost, four games to one, to the Tigers in the World Series, but it was a great run. They wouldn’t again make the postseason until 1996, but they were swept in the NLDS. In 1998, they made it all the way back to the World Series, only to be swept by the dynasty Yankees. There were also a pair of playoff seasons in the 2000s without advancement.

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Their recent run has seen five playoff berths in seven years, but they’ve only made one NLCS (2022), where they were bounced 4-1 by the Phillies. 

Can they make more noise this time? They sure look great right now, but run into Milwaukee, the best team in baseball this round and could have an absurdly difficult road if they somehow get through that one. 

2. Tampa Bay Rays

• 2026 record: 98-64
• Odds to win World Series: +800
• Pennants: 2008, 2020

Perpetual punchlines as the Devil Rays, the Rays dropped the “devil” prior to the 2008 season and, ever since, have been contenders more often than not. They went from a perpetual last-place finisher in the AL East to making the playoffs in four out of six seasons from 2008-13. After a downturn of five playoff-less seasons, the Rays then made five straight postseasons (2019-23). They missed the next two, but they’re now back and had the best AL record this year. 

Coincidentally, the Rays have never lost an ALCS. They’ve only made it there twice and won both times before losing in the World Series. It appears their tough test this time around is in the ALDS and not the ALCS, so the hunch is history stays intact on that front — either the Rays lose the ALDS or make the World Series (2008 to the Phillies, 2020 to the Dodgers). 

They seem likely to be underdogs in the World Series, too, should they make it. Still, they have a decent shot to win their first-ever championship.

1. Milwaukee Brewers

• 2026 record: 103-59
• Odds to win World Series: +500
• Pennant: 1982 

There’s a quirk with the Brewers in that they could join the Astros as the only teams to win pennants in both leagues. The Astros won the NL pennant in 2005 before shifting to the AL and winning five AL pennants and their first two World Series in recent years. The Brewers’ 1982 pennant was in the American League. 

From that 1982 pennant through 2007, the Brewers did not reach the postseason. They made the NLDS in 2008 and the NLCS in 2011 before another six years without the playoffs. Since then, it’s been the golden era of Brewers baseball. This is their eighth playoff berth in nine seasons; they only had four previously. They had been division champs three times in their first 49 seasons and have now won the NL Central in six of the last nine years, including now four straight. 

Still, postseason success has eluded these Brewers squads. They’ve made the NLCS twice in this stretch and lost both times. They were bounced in the Wild Card round four times and the NLDS (after a bye) once. 

The Brewers enter this postseason with the best record in baseball, but the question remains if they can get over the hump — especially after being outscored 15-4 in a four-game sweep by the Dodgers in the NLCS last year. 

Of these three, though, they are the most formidable title threat.