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The POTUS might want to reconsider his position on “bad hombres.” His former daughter in law’s high school sweetheart was a proud member of a street gang.

According to Page Six Vanessa’s Upper West Side prep schooling did not deter her from fawning over a bad boy. Her date to her senior prom was a gentleman named Valentin Rivera; a proud member of the Latin Kings Lower East Side chapter.

In an interview with the publication, her former boyfriend detailed that she lived sort of a double life. During the week she would be an honor student and on the weekends she would drive Rivera around to make drug sales while a pistol was stashed in the trunk.

“We were kids. She liked the street life at the time. She liked that type of environment — being around gang members and stuff” he explained.

The street mystique even rubbed off on her he said. “She got into a couple of little catfights. She was pretty jealous,” he said, “as far as other girls and stuff, she let it be known that I was her man.”

Their relationship ended in 1998 when at the time she was a model for the prestigious Wilhelmina agency and she started seeing Leonardo DiCaprio.

Vanessa married Donald Trump Jr. in 2005. He allegedly had an affair with Danity Kane singer Aubrey O’Day in 2012 which is rumored to be the cause of their divorce earlier this year.

Via Page Six