When Cash WinFall's jackpot rolled down, one couple bought $614K for a sure thing

A WIRED piece on broken lotteries recounts how Massachusetts' Cash WinFall game contained a flaw that was never a secret code — just a moment when the math flipped. When the jackpot reached roughly $2 million and no one won, the game rolled the prize money down into smaller tiers, and payoffs for the small prizes swelled so much that statisticians said a profit was practically assured for anyone buying at least $100,000 in tickets.

In July 2011, Billy's Beer and Wine, a sleepy Western Massachusetts liquor store that had sold $47 worth of tickets the day before, spent three days with its ticket machine tied up as Marjorie Selbee, a woman in her seventies from Michigan, bought $307,000 of $2 tickets; her husband Gerald bought another $307,000 down the road. The couple ran a gambling company, GS Investment Strategies, and were among a tiny group of bettors — including trained computer scientists from MIT and Northeastern — who virtually took over the game during rolldown weeks.

The trick, as the Boston Globe's investigation put it, was not defeating the code but realizing that under certain conditions the average payout exceeds the cost of the ticket — the same method, the article notes, that made Voltaire rich in the early 18th century. It sat in plain sight of a state lottery whose own auditor had already documented 'non-random' payouts to a short list of individuals: one person cashed 1,588 winning tickets for $2.84 million between 2002 and 2004. After the May 2011 rolldown, just three groups claimed 1,105 of the 1,605 winning tickets statewide.

During 'rolldown weeks,' the average payout exceeded the ticket price — so buying $100,000+ of tickets at the right moment stopped being gambling and became an annuity.

The edge came from the game's own payout schedule, published in advance — no insider knowledge required.

Scale was the moat: only buyers who could put up six figures in a three-day window could harvest the roll-down.

The play was repeatable every quarter, converting a lottery into a scheduled, statistically profitable purchase.

It exposed a regulator blind spot: the lottery's own audits had already documented suspicious payout concentration.

Read the payout function, not the jackpot: any game whose expected value crosses above its price at predictable moments can be legally harvested by whoever shows up with scale.

The Boston Globe investigation published in 2011 found the game had been plundered by a small circle; the Massachusetts State Lottery had insisted similar payout patterns were tax-evasion cashing, which the reporting contradicted. No changes of rule are described in the material.