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Dave Roberts, Los Angeles Dodgers
Dave Roberts is, arguably, the most accomplished manager on this list. The Los Angeles Dodgers have made the postseason in each of the eight seasons he’s managed the team, and seven of those postseason berths came from division titles.
The Dodgers have appeared in the World Series three times and won it all in the pandemic-abbreviated 2020 season under the 52-year-old.
Then, you look at the team this year, and it’s a prime opportunity to make another run. The Dodgers are the class of the NL, battling the Philadelphia Phillies for the top seed.
For all of the success under Roberts’ leadership, they have also experienced disappointing postseason finishes with some of the most talented rosters in the league.
The question is whether he can survive another short October.
Aaron Boone, New York Yankees
Everything is positioned perfectly for the Yankees to reach the World Series for the first time since they last won it in 2009.
They traded for Juan Soto to elevate and balance their previously right hand-dominated lineup.
Aaron Judge and Soto lead all of baseball in OPS, although the lineup lacks depth. Their team ERA is the second-best in the AL and ranks third in opponents’ batting average.
They are battling the Baltimore Orioles for the AL East and are certainly a threat in the postseason, even as a potential wild card with their top-heavy star power.
Aaron Boone, especially after a letdown in 2023 when the Yankees only won 82 games, is out of excuses for the team not reaching its goals. A disappointing postseason showing could result in New York moving on.