In March 2018, Santana fled Newark Liberty International Airport, leaving his passport, identification and luggage behind after Transportation Security Administration agents examining his carry-on luggage found a loaded .38-caliber handgun inside of his bag, as well as eight oxycodone pills. After going on the run for three days, Santana turned himself into the custody of the Port Authority Police Department on March 12. On March 26, Santana was denied bail. Santana was released from custody on April 6, 2018, when his mother posted $500,000 bail after putting her house up. He was ordered to remain in the custody of his mother and remained on house arrest at his mother's residence in New Jersey while he awaited a federal trial. He was later allowed to travel and perform with the rest of The Diplomats on their 2018 reunion tour, under the condition that his mother accompanied him at all times. On December 18, Santana was sentenced to 27 months in prison followed by one year of supervised release. Santana began serving his sentence at the medium security FCI Petersburg in Hopewell, Virginia on March 1, 2019. Santana was released from prison early on August 5, 2020, after serving 17 of his 27 month sentence.