I mean if we're just naming a price you could say something like 100m+, invest it for profit for X amount of time and either intentionally or unintentionally slip up at some point, pay back the original and be pretty nicely set with no further catch.
Sure it's clearly not within the spirit of the question, but still.
Possible, but "in debt" can equally mean you just owe the money, it doesn't have to mean bankrupt with the debt on top of it. If you owe your credit card company 10k you're in debt 10k until you pay them, regardless of whether you have 1 million in the bank. Same if you have student loans etc.