I found this last night while I couldn't sleep. Was looking for online episodes of "Lottery Changed My Life" or "Curse of the Lottery" when I came across it.
It's a pretty good show, about an hour and 45 minutes and follows a few people from a group of 16 cafeteria workers and two of the most popular New York Lottery winners. Unlike other documentaries that show how everyone changed for the better by living fancy lives this shows how a few people from the group of cafeteria workers stay mostly the same, still going to garage sales looking for bargains or still running their dairy farm, all while still holding onto most of the cash. Of course it also follows the two NY Lottery winners who have since lost their millions ($5 back in '81 and '82), detailing what they do now, how it was back then, how they lost their money and how they feel about it. Louis Eisenberg, the first $5 million winner, was pretty interesting to listen to, though I will warn at times he's inappropriate (for anyone that gets offended easily).
If you have some time to kill I'd suggest watching it. The site it's on allows you to save your place to go back later and begin where you left off (though entering/exiting full screen during commercials causes the video to mess up and start at the beginning).
http://www.snagfilms.com/films/title/millions_a_lottery_story/