He began dealing drugs in 2005. In April of 2009 he stole a 1999 Mazda Millenia that had been left in his neighborhood, only to discover that the body of Denise Babbit was in the trunk. He drove the car to Santa Monica and left it in the parking lot next to the Casa Del Mar Hotel. However, he left a thumbprint on the rearview mirror. He was arrested for her murder, and Santa Monica police extracted what they construed as a confession from him. He was 16 years old at the time but would have been tried as an adult. His public defender was Jacob Meyer. He was later exonerated when Los Angeles Times reporter Jack McEvoy found evidence that Babbit's murder was actually the work of a serial killer.
Winslow and his grandmother were set to appear on CNN Newsroom along with McEvoy until the reporter warned the show's producer of Winslow's volatile vocabulary and gang affiliation.