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Donald Trump Jr.’s connection to Diddy runs deep, stemming from his father’s longstanding friendship with the music mogul. However, their relationship soured when Diddy publicly endorsed Joe Biden for president in 2020. Despite this rift, Donald Jr. maintained ties with Diddy due to their shared social circles, as he revealed during an interview with DJ Akademiks in April 2024.
Interestingly, Donald Jr.’s connection to Diddy also extended through his ex-wife, Vanessa Trump, who was close friends with Kim Porter, a longtime partner of Diddy. Donald Jr. disclosed that Vanessa and Kim were inseparable, often participating in photoshoots together. Intriguingly, Donald Jr. raised suspicions about Porter’s untimely death in 2018, claiming that she expressed fear of Diddy to Vanessa. However, officials certified her death as natural, and Diddy publicly mourned her passing.
Additionally, Donald Jr. was linked to Diddy through his alleged affair with singer Aubrey O’Day, who gained fame on Diddy’s “Making the Band” in 2005. Reports of their affair surfaced during Donald Jr.’s divorce from Vanessa in 2018, prompting O’Day to speak openly about her relationship with him. Following Donald Jr.’s interview with DJ Akademiks, O’Day took to social media to address the discussion, hinting at insider knowledge without divulging specifics.
In subsequent tweets, O’Day defended Donald Jr.’s intelligence and reiterated her admiration for him, even referring to him as her “soulmate” in a previous interview. However, she also shared her experiences of working with Diddy, describing a tumultuous environment marked by racism and sexism. Despite these challenges, O’Day remained steadfast in her support for Donald Jr., emphasizing his intelligence and integrity amidst controversies surrounding their respective relationships with Diddy.