Gary Kings pattern of reckless behavior could jeopardize his future on Below Deck Sailing Yacht. Gary first appeared on the show in season 2 and has been a pivotal member of the cast ever since. As First Officer, Gary strives to one day become a captain. However, he has also developed a reputation as a womanizer. Garys recent actions could put his yachting future at risk and make season 5 his last.