Jerry and Marge Selbee

Jerry Selbee, a retired Kellogg's materials analyst with a mathematics degree from Western Michigan University, was 64 when he read a brochure for Michigan's new Winfall game in 2003 and found its flaw within minutes. When the jackpot passed $5 million with no six-number winner, the pool 'rolled down' to lower prize tiers, and on those draws the expected value of a $1 ticket exceeded $1. His first wager, $2,200 placed in Mesick, returned $2,150; his second turned $8,000 into $15,700. He and his wife Marge formed GS Investment Strategies LLC, which grew to 25 shareholders buying $500 units, and played 12 roll-downs for about $850,000 in profit before Michigan discontinued Winfall in May 2005. They then drove roughly 900 miles to Massachusetts to play Cash WinFall from August 2005 until the game ended in January 2012, buying tickets by the hundred thousand, including $720,000 on 360,000 tickets for the 14 July 2011 draw. The Boston Globe exposed the high-volume syndicates on 31 July 2011. Massachusetts inspector general Gregory Sullivan's report of July 2012 found the lottery had bent its own rules for large bettors but that no laws had been broken. Over nine years the Selbees grossed about $26–27 million and netted roughly $7.75 million before tax.

In a June 2022 CBS 60 Minutes update the Selbees were still living in Evart, Michigan, and said they now gathered with their former investors for poker nights rather than lottery runs; their winnings had gone on renovating their home and on education for their six children, 14 grandchildren and 10 great-grandchildren. Paramount+ released a feature film about them, 'Jerry & Marge Go Large', starring Bryan Cranston and Annette Bening, in June 2022.