After years of trying, someone in Florida has finally claimed the Mega Millions jackpot – the third-largest prize in American history, though taxes will likely reduce it by about one third. The winner chose anonymity and now has 60 days to claim his or her prize that was announced Monday night.

Now, the big question for lottery ticket holders is how they want to take their winnings – in lump sum or an annuity over 30 years. If they opt for an annuity option, federal taxes withheld at 24% may also need to be taken out in addition to state income taxes (like Illinois).

Lump sum payment may seem like the easiest solution, but it may not always be best. Winners could end up spending their winnings too quickly on bad investments or overspending according to Warren Racusin of Lowenstein Sandler in New York – often falling victim to family members requesting more of their winnings than anticipated.

Lottery winners often face unexpected financial hurdles after their big win, and the time and energy it takes to manage such an immense sum can be draining. Some individuals simply are not adept at managing such amounts and that can lead to costly mistakes such as making poor investment choices or incurring credit card debt, says Forbes contributor Christopher Eadie.

One of the biggest mistakes comes from failing to plan ahead or hire professional assistance, like Denise Rossi who won $1.3 million from California lotto in 1995 and kept it secret from her husband – demanding a divorce without telling him she won! Two years later he intercepted a letter that revealed this secret, filed suit for wrongful termination and won every cent of Denise Rossi’s winnings!

Other large lottery wins have turned out to be disasters for their winners as well. Welshman Luke Pittard won a $1.9 million jackpot in 2006, yet spent almost all of it on trips and wedding expenses; soon thereafter he found himself flipping burgers at McDonald’s.

Few lottery winners manage to make smart financial decisions and use their prizes responsibly, but most end up making misguided choices that cost them their fortune. Here are a few major lottery winners who fell from grace: