Can't remember if I've talked about it here or just in fic wips, but I like to HC that Dante is Actually Cursed levels of unlucky. Like, it isn't just that he *seems* kind of unlucky based on his circumstances, he's "loses 85% of the time on a 50% chance" kind of unlucky. He *will* consistently get tails 8 or 9 times out of 10 when flipping a coin and trying to get heads, or rolll a 1 or 2 five times in a row when playing a game where you want to high roll (reasons to destroy the DMC4 Dice, anyone?)
Lady and Trish actually discretely kept track a few times and did the math to come up with this number before telling him. They noticed it mostly applied to things that depend on pure luck/random chance like games with draws and rolls and so on, but he's had enough weird cases of being dealt a bad hand by fate that they're pretty sure it impacts everything to some extent. Dante mostly takes it in stride though, deciding that there's nothing he can do about it so he'll just do as he pleases. So what if he has crummy luck; he'll make up for it with skill. Or just take advantage of it. Maybe at some point he and the ladies go to a bar where they egg him into joining a game where they bet against him because it's pretty much guaranteed he'll lose and they'll profit big time. (Unless of course the "bad luck" comes in the form of him doing uncharacteristically well to the point that Lady and Trish lose their money because Dante suddenly couldn't stop rolling 6s. Bad luck comes in many forms, and some of them can seem good on the surface!)
Nero, on the other hand, is a "wins 70% of the time on a 50% chance" kind of guy because a ton of his skills are named after gambling stuff. Yes Dante has the Jackpot phrase, but otherwise he doesn't have the same sort of skill list so I think it would be hilarious if both Dante and Vergil have terrible luck while Nero's somehow wraps around to being pretty lucky. I think Dante would find it funny while Vergil would (not-so-) secretly be jealous.