What happened: Dustin May holds a rare distinction after being traded to or from each of the last two World Series champions. The right-hander, who credited Milwaukee's 'next guy up' mentality during the Fall Classic, won a title following his departure from the Dodgers.

Why it matters: Player movement directly linking back-to-back title winners remains rare across Major League Baseball history. May now enters the winter market after declining his mutual option with Milwaukee, positioning him among the notable free-agent arms available.

What to watch: May will test the open market as teams begin shaping their rotations for the 2027 season.