Here's One of Trump’s Daughter-In-Law Who Allegedly Dated a Latino ‘Gangster’

After marrying Donald Trump Jr. in 2017, Vanessa Trump joined America's first family. However, she had a troubled youth of her own. A friend of Vanessa's told GQ that she dated a young guy called Valentin Rivera, who claimed to be a member of the Hispanic gang the Latin Kings and she remembered that Vanessa 'spoke with an urban, gangster accent.'

The friend revealed to the outlet, "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. She was somebody who went out of her way to intimidate people by having a scary boyfriend that could hurt people." Despite her family's opposition, Vanessa visited Rivera at Rikers Island while he was in prison for assault. Vanessa's feelings for Rivera were as intense as any adolescent could be. 

During the same year, Rivera spoke with Page Six about how Vanessa would drive him about in her stepfather's convertible, which had an illegal pistol in the trunk, to assist him deliver pot to pals. Their first encounter, which occurred during Rivera's fifth grade at P.S. 158 on the corner of 77th Street and York Avenue, was already fraught with tension. He recalled, "We was in the carnival in the school and I hit her with a water balloon, and she told on me. I went to the principal’s office. Then we parted ways until a couple of years later."

A little over a year after they began dating, Rivera was sentenced to one and a half to four years in jail for violent assault. Vanessa, visited Rivera on Rikers Island with Rivera's mother before he was sent to an upstate maximum-security adolescent jail. He told the outlet, "She was heartbroken that I was being taken away. The first time [she came to visit], she was upset — she cried a little bit — but after a while, we get used to things. She only came to visit me twice because her mother forbid her from coming to visit me." Rivera went on to say that he and Vanessa were very much in love and had even considered marriage and starting a family. Unfortunately, Rivera's 1998 New York Post exposé of Vanessa's infidelity with Leonardo DiCaprio put an end to their five-year relationship. Vanessa was a model for the Wilhelmina agency at the time.

Interestingly enough Donald Trump conducted his research before Vanessa wed his son and found out that she had dated a Latino gangster. Trump questioned Vanessa over her connection with Rivera after summoning her to his office. however, she denied it completely. Vanessa and Donald Jr. tied the knot in 2005, and they have five kids together. After 12 years of marriage, the pair announced their divorce in 2018. As reported by People, they shared a joint statement at the time, "After 12 years of marriage, we have decided to go our separate ways. We will always have tremendous respect for each other and our families. We have five beautiful children together and they remain our top priority. We ask for your privacy during this time."