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Jun 29, 2026

Yankees Monday Mailbag 6/29: World Series Odds, Trade Deadline Decisions and Replacing Boone With AI

Yankees Monday Mailbag 6/29: World Series Odds, Trade Deadline Decisions and Replacing Boone With AI

Readers questions for this week's Yankees mailbag focus on the Yankees chances at the World Series and wondering if a robot can take Aaron Boone's job.Joseph Randazzo|
New York Yankees manager Aaron Boone (17) walks back to the dugout in the sixth inning against the Detroit Tigers at Comerica Park.
New York Yankees manager Aaron Boone (17) walks back to the dugout in the sixth inning against the Detroit Tigers at Comerica Park. | Rick Osentoski-Imagn Images

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New York Yankees

To submit your questions, reach out to Joseph Randazzo on X or Instagram at @YankeeLibrarian.

Here are answers to five of the most pressing questions that were on Yankees fans' minds this week:

Do you think they have a chance at winning the World Series?@gskiff35, Instagram

If the team in October is rolling out Spencer Jones, Jasson Domínguez, Oswaldo Cabrera, Amed Rosario, and Austin Wells all at once, their chance at winning a World Series is next to nothing. Assuming they're healthier by the time the playoffs get here, they should have as good a shot as anybody to win a World Series.

This team will look much better than the one that's on the field right now, and by then, Gerrit Cole will also have more reps. Same with Carlos Rodón, but it's hard to trust his playoff résumé.

Which reliever should the Yankees most aggressively pursue before the deadline?@Joenajarian, Instagram

It would have been great if the Philadelphia Phillies had continued being bad. They have turned things around, though, so Jhoan Duran likely isn't available. I don't expect Mason Miller to be available either. The Padres usually add at the deadline if they have a chance, and they're not so far out of the wild-card hunt.

Just combing through the teams that look to be out of the playoff picture, one underrated name that's intriguing is Chase Silseth from the Angels. Silseth was part of that Angels draft, where they focused on pitching that year, and he looks to be one of the best from that class. He averages 96 mph on his fastball and has a 30.4% hard-hit rate.

Los Angeles Angels pitcher Chase Silseth
Los Angeles Angels pitcher Chase Silseth (63) celebrates with catcher Logan O'Hoppe (14) after beating the Arizona Diamondbacks at Chase Field. | Matt Kartozian-Imagn Images

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