"The upside sounds nice. So what's the problem exactly? Well, for starters, it preys on the same instinct that drives parlays. You bet a little to win a lot, and you make correlation work for you, but here the correlation has already been priced in. The books are well aware of how it works. You're not compounding a stake. Instead, you're making a series of independent bets on each rung. And that's why ladders really treat your bankroll like a Margaritaville mermaid. You see, it's a giant blender. It's a gimmick for Jimmy Buffett fans. Just ask your dad about it. It's because you're paying VIG on each bet. And as those bets go higher up the ladder, the more each rung carries more VIG. Especially after you move past two-way props. At least then, you can see exactly how much juice you're paying. When you get to the higher rungs, they become one-way markets where the books can hide all the VIG they want."