Vanessa Trump earned her “ill thug” rep. As a teen, she embarked on a five-year romance with the Latin Kings’ gang banger, Valentin Rivera. And Vanessa was totally ’bout that action. “She wore big hoop earrings, hair slicked back. She thought she was a gangster. She had a gangster boyfriend, and she acted like a gangster herself,” a friend told GQ. “She was somebody who went out of her way to intimidate people by having a scary boyfriend that could hurt people.”
Rivera claimed Vanessa carried out drug drop-offs and drove around with illegal firearms in her stepdad’s car, while he made sure everybody knew not to mess with his girl. “If anybody disrespected her in any way, I would physically put my hands on them,” Rivera told Page Six. “Any type of disrespect — call out her name, mess with her, anything.”
Vanessa was totally heartbroken when Rivera caught eighteen months on assault charges. He was held on Rikers Island while waiting for a transfer upstate, and Vanessa regularly visited along with his mom. “The first time [she came to visit], she was upset — she cried a little bit — but after a while, we get used to things,” he said. Vanessa was waiting for Rivera when he was released, and they talked about getting married and having kids. However, he called things off in 1998 after learning Vanessa cheated with Leonardo DiCaprio. Rivera said Vanessa had wanted five children, a dream she later achieved with Donald Trump Jr.
