The Tampa Bay Rays and Milwaukee Brewers are about to collide in the 2026 World Series, and the matchup brings together the best team in the American League and the best team in all of baseball. Tampa Bay finished the regular season with the top record in the AL, while Milwaukee owned the strongest mark in the sport overall.
On paper, it’s a heavyweight series. In practice, it may come down to one Rays player most people won’t immediately put at the center of the conversation.
That player is Chandler Simpson.
The Rays will draw plenty of attention because of names like Junior Caminero, Drew Rasmussen and Yandy Diaz, but Simpson has the kind of skill set that can tilt a series in a hurry. In a matchup this tight, his value goes beyond the usual headline-grabbers. He’s the kind of player who can keep pressure on a pitching staff all series long.
At 25, Simpson has already established himself as one of the most dangerous runners in the game. He led the league with 46 stolen bases this season, and he also hit .306.
He doesn’t bring much power - he has yet to homer in his big league career - but he can change the shape of an inning fast. A single can become a double.
A double can become a triple. That’s the kind of speed that forces defenses to hurry and pitchers to think twice.
He’s kept that same edge in October. Through eight postseason games, Simpson has already swiped three bags. The bat hasn’t been especially hot, but he’s been getting on base enough to matter, and that’s enough when a player’s legs can do this much damage.
He also brings value in left field. Simpson is regarded as one of the better defenders at the position, even if the arm is not a strength. Still, the 25-year-old ranks in the 94th percentile in outs above average.
If Tampa Bay ends up winning the title, Simpson might not be the obvious choice for World Series MVP - though it’s not out of the question. But whether the Rays beat Milwaukee or not, his impact could be the difference in the series.
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How The Brewers Keep Building Winners Without Spending Like Contenders
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For Tampa Bay, the reminder is less about payroll than about roster construction and how thin the margin can be when so much of the group comes from outside the system. Free agency has barely mattered for either clubs core, but the Rays path has been especially dependent on identifying the right pieces and fitting them together quickly. The unresolved question is whether that model can keep producing October-caliber teams when the talent pipeline looks different from Milwaukees and the margin for error stays so small. [Read more 🡒]