Thanksgiving With Pimp Chicago
We wanted to get into the Players Ball. He told us he could help.
Hi Everyone,
It’s been a minute, my apologies. Got waylaid working on this book. For a couple of years I spent Thanksgiving with different iconic American subcultures. I should have continued! These pictures are low-res files shot by the English photographer Chris Anderson (not the Magnum guy), with whom I lost touch several years ago. If you’re out there Chris, get in touch!
Thank you as always for reading, and hopefully I’ll see you in the comments.
Sanjiv
“We Family Now.”
It was 3am when Billy finally brought the van to a halt. We were in a motel car park beside the freeway, somewhere near Gary, Indiana. Exactly why we’d stopped I couldn’t say, only that when we left the party over two hours ago—me and Chris, the photographer, and Billy and his boss Pimp Chicago. We were supposed to collect two prostitutes from a truck park near the Illinois border, but we sailed past that state line 60 miles ago and still no sign of Gypsy or Aphrodite.
“What did I tell you about pimping? It’s a business, that’s right. And in business you got to pay. Now you want to go to the Players Ball, but you don’t want to handle your business. So what—you trying to pimp us?”
As Billy spoke, Pimp Chicago sat imperially silent in the passenger seat. It’s a pimp’s affectation to have assistants and such, so Billy served variously as his minder, driver, gopher and, on special occasions, his door-opener. He was the Walmart version of that guy who went around holding a parasol for P-Diddy. But he’s also Chicago’s older brother by six years—he was 46 then—a double drop in seniority which has done nothing for his general charm.
“Now Chicago don’t need your money, he got money. Tell me, does he look like a man who needs money?”
In a pumpkin suit, flashing rings and twinkling cherry gators, Pimp Chicago delicately tweaked the tilt of his strawberry hat in a wing mirror. A bony five-two, he put the imp in ‘pimp’, an elfin dandy, dressed for a tap dance.
“But you gotta pay the Bishop,” Billy went on. “Everybody pays that n*****—Snoop Dogg, HBO, everybody. So you making a big problem right now, and this ain’t no game–”
Chicago silenced Billy with a wave and turned briskly to look me in the eye. “Now don’t be scared,” he said, quietly. “Stick with me and the Bishop can’t touch you. We family now—didn’t I invite you in my house, didn’t I introduce you to my mother? Well then.” He pulled his jacket to the side and revealed a handgun tucked into his belt. “You know I carry this, right? So I ain’t scared of no Bishop, I ain’t even scared of no penitentiary. I already did 15 years and I didn’t mind. I go there again tomorrow.”
I first met Pimp Chicago a few days earlier because I wanted to go to the Players Ball, an annual pimp convention from which the press are typically banned. I was originally meant to go with Pimp Domination from Miami but one of his girls had been choked in Las Vegas so he couldn’t afford to travel, what with the hospital bills. Domination passed me onto his pimp friend Whitefolks, but Whitefolks couldn’t get me in, so he introduced me to Pimp Chicago. And for a few days it had been going just fine. But now, not so much. Was he going to rob us? Would he take us back to our hotel at least, or leave us here in the icy nowhere?
“Listen, I’m a get you in that Ball tomorrow,” said Chicago, “but you gotta pay the Bishop. That’s how it is.”
At the first cash machine we found, I withdrew as much as Barclays would permit. The rest, I assured him, would be tomorrow.
The Bishop’s Last Bash
The year was 2003. A simpler time as Gen Xers like to say. So why am I telling this story now? Because, well, two reasons:
1) It’s Thanksgiving and this is a Thanksgiving story. Just a couple of days before robbing me, Chicago had me over for turkey and fixings (God bless America).
2) It’s as relevant today as it was then. Which is a shame and it points to a problem with liberal identity politics, one that we should probably fix. We think the world changes, and we’re so much more enlightened now. But does it? Are we?
