Jackpot seems to have "lucky" built into his core programming. He really gets a kick out of placing bets on dangerous predicaments and coming out on top. The higher the stakes, the happier he is. He once bet a Decepticon guard he could escape from the cell he was being held in... and now that Decepticon is in the cell Jackpot formerly inhabited.
To tilt things even further in his favor, Jackpot relies on his avian partner Sights to scout out information beforehand. Of course, some are just waiting for the day Jackpot's luck runs out... which might have disastrous results for the Autobot.
Jackpot has a big thing for fembots (especially ones with racing stripes), despite it being the one aspect of life where he isn't (getting) lucky.