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Jimmy Kimmel Roasts Diddy’s Trump Connections in Monologue

5/23/2025

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Summary

Story summary

Jimmy Kimmel brought the house down with laughter during his Wednesday night monologue, poking fun at Sean “Diddy” Combs’ surprising connections to Donald Trump. Although Trump isn’t involved in Diddy’s trial, Kimmel quipped that Diddy’s frequent events at the Trump International Hotel could tempt Trump to consider a pardon. The trial unfolds in New York, adding to the intrigue.

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Story summary

Jimmy Kimmel brought the house down with laughter during his Wednesday night monologue, poking fun at Sean “Diddy” Combs’ surprising connections to Donald Trump. Although Trump isn’t involved in Diddy’s trial, Kimmel quipped that Diddy’s frequent events at the Trump International Hotel could tempt Trump to consider a pardon. The trial unfolds in New York, adding to the intrigue.