O. Henry saw this coming.

The humor writer who specialized in trick endings wrote a short story that always bothered me, called “The Cop and the Anthem.” It concerns a street bum who wants to get sent to a warm prison for the winter. “Soapy” keeps trying to get arrested, but can’t seem to get caught. Finally he slumps onto a park bench in frustration, and hears a soaring hymn being played by the organ of a nearby church. It inspires him; he decides to turn his life around, get a job, make something of himself. He is about to begin, when a policeman arrests him for loitering on the bench—and poor Soapy gets sent to jail, his dream of a new life aborted.

Now comes the saga of Timothy Elliot of Hyannis, Mass., a confessed bank robber who suffers from mental illness. He is currently out of jail on probation. One of the conditions of his probation was that he could not gamble or buy state lottery tickets.

A pause here for reflection. The state lottery is sanctioned by the government, the legislature, and the people of Massachusetts. To listen to lobbyists, it isn’t even gambling, but rather “gaming.” The fiction supporting lotteries is that it’s a good for everyone. The state gets needed revenue, the public has “fun”(you know how much fun it is scratching off those tickets), schools get built, roads get paved, and every now and them some lucky stiff becomes filthy rich. Why would in the world would a judge forbid such a benign activity?

But he did…maybe because he agrees with the Scoreboard that state lotteries are craven and misleading devices to take from the poor instead of taxing the rich. And Elliott defied his probation terms by buying a ticket, a relatively safe violation, unless he had the bad luck to win. Which, God being a real cut-up these days, he did.

A million dollars.

Now a hearing is going to be held to determine not only whether he can keep the money, but whether he will have to go to jail for buying the ticket. The Scoreboard would normally approach this matter by pointing out that terms of Elliot’s probation were clear, and he violated them. The fair result is unambiguous: he should go back to jail. But in this case, special compassion and empathy is called for. Like O. Henry’s star-crossed bum, Elliot has finally reached a point where he can turn around a life of bad decisions and worse results. A life-time loser finally hits the jackpot, and it gets him sent to jail? This is worse even than Soapy’s ironic fate! How can Massachusetts go ahead promoting its lottery and then let its courts behave as if buying a ticket is proof of moral turpitude? If the judge’s prohibition on playing the state lottery was intended to protect the incompetent bank-robber from losing money, that prohibition would seem to be rendered moot by the million dollar bonanza. And if he feels the lottery is such a disreputable activity, well, his employers run the thing; targeting poor Elliot seems to be an inappropriate way of making his objections known.

This is a time to make an judicial exception if there ever was one. Let Elliot keep the money, start a new life, maybe do some good for his fellow man. Doing otherwise may not meet the Constitution’s definition of “cruel and unusual punishment,” but it would be too cruel nonetheless. Give Elliot a break; the alternative is too awful to contemplate.

Do it for Soapy.