Surviving Barstool | Ep. 2 Premieres TONIGHT at 8PM ETWATCH EP. 1 NOW

This Chicago Man Loves Felony Convictions More Than You Love Your Mother

unnamed(CWB Chicago) – A 15-time convicted felon who’s on parole is now charged with mugging a man in Rogers Park less than 100 yards from the location where he robbed another man in 2016. Prosecutors said a police sergeant was on patrol on October 27th when he saw 2 men having a dispute. That’s when the sergeant saw 49-year-old career felon Dewitt Brown begin to take valuables from the other man’s pockets.

When the sergeant intervened in the robbery, Brown allegedly said: “I ain’t going down like this!” Brown then turned around, ran a few steps, collided with a wall and fell to the ground, the sergeant reported. As Brown was lying on the ground, he began to take items out of his jacket pocket, including a pay stub, a Ventra card, and an LG ph1, all of which belonged to the 50-year-old robbery victim, police said. Prosecutors charged Brown with felony robbery and Judge Sophia Atcherson set his bail at $10,000.

According to state records, Brown’s prison sentences so far include:

• 3 years for unlawful restraint in 2016
• 2 years for theft in 2015
• 3 years for theft in 2012
• 8 years for aggravated robbery in 2007
• 2 years for retail theft in 2006
• 2.5 years for retail theft in 2004
• 3 years for retail theft in 2003
• 2 years for theft from person in 2002
• 1 year for retail theft in 2002
• 6 years for narcotics in 1997
• 2 years for manufacture-delivery of look-alike drugs in 1996
• 6 years for robbery in 1993
• 4 years for narcotics in 1992
• Another 4 years for narcotics in 1992
• Yet *another* 4 years for narcotics in 1992

Most people I know quit something as soon as they can. People love quitting non addictive things. It’s our ancestral right. And when it comes to crime, most of the people I know give up after their  3rd or 4th felony conviction. Rarely do they get to 15, and rarely do they put up 52.5 years worth of sentencing in the process. They say it’s too much work getting routinely violated in a poorly run, rural, medium-security penitentiary day after day after day. That the criminal justice labor market is brutally unfair. That the food sucks and the air conditioning runs a little soft in July. That basically prison blows and if you can avoid it, do so at all costs.

And then there’s a guy like Dewitt Brown, possibly the least effective petty criminal in Chicago’s long-storied history of crime. A man who somehow notched 2 years’ of prison time for each year lived from 1992-2018. A man who transcends being a piece of shit with a prison record that reads like Goose Gossage’s Hall of Fame plaque.


4 years here. 2 there. Another 3 here. Blah blah blah at some point it has to be exhausting. Like at some point you have to just accept that you suck at robbing people and selling drugs. Maybe not a bad time to start looking at crypto-currency and other emerging markets to make a quick buck like the rest of us. Or maybe sign up for one of those banger promos on Fan Duel that could net you whatever it is we are peddling. Which reminds me go to Napleton River Oak’s Chrysler Dodge Jeep Ram and tell them Red Line Radio sent you for a $20 oil change. Come for the crime blog stay for the oil change.