On December 10, 2018, O'Brien was arrested in Tampa for burglary of a house in the 4700 block of Windflower Circle near the Northdale Golf and Country and for assault on a responding deputy. Reports showed that around 6:57 p.m., he entered a home without permission from its two unidentified occupants. After one occupant told him to leave, O'Brien pushed a woman to the ground, left the house and hid in the property's backyard until police arrived. A responding deputy gave him orders; instead of complying, charged at the deputy with a knife. The deputy then tased him, taking him into custody afterward. He was booked into the Hillsborough County Sheriff's Office on charges of burglary with assault or battery and aggravated assault on a law enforcement officer, and was being held without bail. The burglarized home is in the same area of a golf course where a house fire broke out about the same time at 16311 Norwood Dr., the house O'Brien was renting. It was not immediately clear if the fire was connected to his arrest.