"Lately it occurs to me, what a long, strange trip it’s been."

The Grateful Dead weren’t singing about Dustin May’s World Series journey in the song “Truckin,’” but they might as well have been. Every season and championship run has its share of twists and turns, but May just pulled off something unprecedented. 

Let us explain. 

May made his MLB debut in 2019 and pitched in the 2020 World Series en route to a title. He missed the entire 2024 season after Tommy John surgery and an esophageal tear. 

He began the 2025 season with the Dodgers before being traded to the Red Sox at the deadline. Traded away from the eventual World Series champions. 

He signed as a free agent with the Cardinals in the offseason, getting off to a solid start that made him an attractive target at the Trade Deadline yet again. 

He was traded to the Brewers, and the rest was history, with May pitching in a second Fall Classic and again emerging a champion.

How rare is that — to be traded away from the eventual champions in a season, only to then be traded to the eventual champs midseason the following year? Glad you asked, and with help from the Elias Sports Bureau, we have a fun answer. 

May is the third player to play for multiple teams in each of two straight seasons, playing for the eventual champs in year one before ending the season on a different team, and then be on the active roster of the World Series champs in year two. Got that? In other words, he’s the third to change teams midseason in consecutive years, first away from the subsequent champions and then to them. 

Lee King played for the Giants in 1921 before being traded in July to the Phillies in a deal that landed New York Casey Stengel. The Giants went on to win the World Series. Then in 1922, he began the season with Philly before having his contract purchased by a team in the American Association in May. In August, the Giants reacquired him and went on to win it all again.

The other player to do this was Dal Maxvill. He began his year with the A's in 1973 before being sent to the Pirates. The A’s won it all for the second straight year (more on that in a moment). Then in 1974, he started with the Pirates before being released in late April. The A’s picked him up a few weeks later and went on to win their third consecutive championship. An additional twist here? The first A’s title in this run was 1972, a season Maxvill began with the Cardinals before being traded to Oakland in August. 

That’s the duo May joined, but his situation is still even more unique. Both King and Maxvill did this in years where the same team won the title in each year, thus they were reacquired by a team they’d already been on.

May is the first player to depart the eventual champions midseason in one year and then join a new club midseason the following year and go on to win it all. 

A long, strange trip indeed. And a singular accomplishment.