Pimp Chicago and the Players Ball

The Times, Jun 2003

Monster’s Ball: The pimps competing for the Pimp of the Year title at the Chicago Players’ Ball live up to every cliche. There is the pantomime wardrobe, the alligator shoes, the empty boasts – and the underlying threat of violence and extortion that make up this self-glamorized and ugly underworld.


Photographs by Chris Anderson

It is 3am when Billy finally brings the van to a halt, in a motel car park beside the freeway, somewhere in Indiana. I don’t know where we are exactly, or why we’ve stopped, only that when we left the party over two hours ago – myself, the photographer, Billy and his boss Pimp Chicago – we were supposed to collect two prostitutes from a truck park near the Illinois border. Well, we sailed over that state line 60 miles ago and with still no mention of Gypsy and 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 me?”

As Billy talks, Pimp Chicago sits imperially silent in the passenger seat. It’s a pimp’s affectation to be attended by servility so Billy serves variously as his minder, driver, gopher and, on special occasions, his door-opener. At 46, he is also Chicago’s bigger brother by six years, 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 bright pumpkin suit, flashing rings and twinkling cherry ‘gators’ (alligator-skin shoes), Pimp Chicago delicately tweaks the tilt of his strawberry hat in a wing mirror. At only five-two and bony with it, he looks like the imp in ‘pimp’, an elfin dandy poised for a tap dance.

“But you gotta pay the Bishop, everybody pays that nigger – Snoop Dogg, HBO, everybody. So with you not paying you making a big problem between the Bishop and my boss, here. That’s right. And I’m talking guns or whatever you got because this ain’t no game-”

Chicago silences Billy with a wave and turns briskly to look me in the eye. “Now don’t be scared,” he says, quietly. “The Bishop ain’t going to touch you. You like family to me now – didn’t I invite you in my house, didn’t I introduce you to my mother? So don’t worry, I got your back.”

He pulls his jacket to the side and reveals a handgun tucked into his belt. “You know I carry this on me, right? Nine millimetre.” He takes it out briefly “So you see, I ain’t scared of no Bishop, I ain’t even scared of no penitentiary. You fucking with a thug nigger now. I alreadydid 15 years for double homicide. And you know what?” He replaces his gun. “I didn’t mind. I go there again tomorrow.”

I first met Pimp Chicago a few days ago because I wanted to go to the Players Ball, an annual pimp convention from which the press are traditionally banned, and he might be able to get me in. First Pimp Domination from Miami was going to walk me in, but he claims one of his girls was choked in a Las Vegas hotel room and the hospital bills drained his cash so he couldn’t afford to travel to Chicago. So Domination told me that his pimp pal Whitefolks would look after me, but Whitefolks had no sway with the Ball organisers so Whitefolks introduced me to Pimp Chicago. And now it has all gone horribly wrong. Is he going to hurt us or just rob us? Will he take us back to our hotels, or abandon us here in the icy nowhere? What does he want?

“Listen, I want you guys to get into the Ball,” says Chicago, “but I need $1000 to pay the Bishop otherwise you don’t need to show up tomorrow. You need to leave town.”

At the first cash machine we find, I withdraw as much as Barclays will permit. The rest, I assure him, will be tomorrow.

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Of all the difficulties in attending a pimp convention, I had not anticipated robbery. Perhaps some dispute at the door over my sartorial shortfall but not a mugging on the eve of the event by the soon-to-be 3rd runner up Pimp Of The Year. After all, the pimp of popular culture is a harmless sort, a ghetto jester known less for gun-thuggery as for a pantomime wardrobe and an unrelenting stream of jive known as ‘game’. He’s a stud, a charmer, he’s the charismatic slum cat Curtis Mayfield sang about on ‘Superfly’, and although he inspires outrage for flaunting his abuse of vulnerable women, he clowns it up with such gusto that before revulsion has a chance to gather itself, it is distracted by a wisecrack, by those ridiculous shoes.

On television, if not in motel car parks, pimps are a joke. On the Jenny Jones show, for example (a low-rent Oprah), the sunny daytime host invited Pimp Domination to strut and brag for her baying audience. When he spun a little rhyme about ‘selling booty by the pound’ and ‘breaking bitches before they hit the ground’, Jones just laughed and moved on. Had he sold ‘crack by the stack’ instead she might have taken issue with him, but he’s not a nasty drug dealer, he’s just a pimp. He’s there to be laughed at.

Even on dedicated documentaries, pimps are more or less handed the microphone by film-makers all too quick to bank on the give-em-enough-rope card. In both Pimps Up Hoes Down (1997) by HBO, and the marginally better American Pimp (1998) by the Hughes brothers (Menace To Society), the camera mostly marvels at the clowns a-clowning, at their big mouths, bad taste and spangly suits. Admittedly, their brazen political incorrectness is fascinating – would you look at that, a whole convention for men who beat women and call them ‘bitches’! But add a classic funk soundtrack and trace the pimp’s inglorious heritage from his slave roots, through his 1970s heyday to his current embrace by hip hop, and the effect is one of grudging respect, even awe for this African American icon – for his defiance of poverty, his contempt for authority, his swagger and front and endless capacity for self-aggrandizement. (Not to mention those shoes).

The pimp owes his current rude health to hip hop culture which has long treasured its urban outlaws. Beside the drive-by murderer, at least, the pimp is a positive role model – he’s friendlier and funnier and with those suits he looks like just another 70s revival. Yet hip hop’s leading lights venerate these gaudy dinosaurs as elder statesmen and pioneers. The multi-platinum likes of Snoop Dogg, Jah Rule and Jay Z are so proud to associate with pimps and sing about pimping that many even claim to be part-time pimps themselves, as a badge of credibility. With pimps now guesting on rap records and presumably picking up handsome royalties, it’s unclear as to who is basking in whose glory any more. On Snoop’s latest single, for example – ‘Paid Tha Cost To Be Da Bo$$’ – you’ll find a few verses by his dear friend and “spiritual advisor”, the most notorious pimp in America, Bishop Magic Don Juan. (Or he who shalt be paid, according to Pimp Chicago).

The Bishop is pimping’s figurehead. He built his reputation in the 1970s, cruising around the depressed suburbs of Chicago’s Southside in a trademark green and gold Rolls Royce: “green for the money and gold for the honey”. He carries an encrusted cane or ‘pimpstick’ with which he once freely beat his girls, the Juanettes, all of whom were tattooed ‘property of Don Juan’. And although he claims to have retired 17 years ago – having heard God’s call after a heavy drugs binge, Don Juan established a crew called Church and ordained himself Bishop – he has remained the public face of pimping, with appearances on Pamela Anderson’s “VIP”, on Dr Dre’s movie “The Wash” and several chat shows.

Much of the Bishop’s profile stems from his control of the Famous Players Ball, an annual event he founded in 1974 and has thrived ever since. From year one, he was astute enough to merge what might have been a mere tribal meet with both his birthday party (November 30th) and an awards ceremony (the Ball is like the Pimp Oscars). The awards themselves are comical – Mack of the Year, Pimp of the Year, Cross-Country Pimp of the Year and so on – but they keep the sheep flocking from Hawaii to far and wide, all desperate for the validation of their peers, and, lately, the chance to appear on television or to cosy up to the stars that the Bishop brings along like Snoop Dogg and Ice T (both proud pimps themselves). This year, the posters promise James Brown, though few believe it.

For the Bishop, the Ball makes shrewd business sense. Not only does it establish Church as the Pimp Vatican – similarly led by an old man with a big ring – but since the Bishop is the host, sole judge, sanctioning body and promoter of the event (not to mention the birthday boy), it also assures him a bounteous stream of ‘blessings’ around this time of year. The way pimps queue to approach the Bishop with an envelope and a hug, one is reminded of the Sicilian Mafia.


“All the Bishop knows about church is the goddam collection plate,” curses Pimp Chicago. “That’s why a lot of niggers don’t fuck with Church no more. Some niggers be giving him ten, twenty thousand dollars for pimp of the year. I ain’t spending no $20,000 for no $40 plastic trophy!”

It is the Thanksgiving holiday, 48 hrs before our mugging, and after a hearty turkey dinner, Pimp Chicago – or Ronnie as he’s known at home – settles down to tally the cost of the impending Ball. “I got to buy my outfit, my bitches’ outfits – that’s $3000 right there, because all my shit is tailor-made. Then I got the limo to pay for, my shoes…” He wipes his forehead. “Damn! Today was expensive enough!”

Since morning his cramped three-bedroom has been overrun by family and friends all heaping their paper plates with his food, smoking his menthols and drinking his liquor out of plastic cups. Among them was his mother, a cleaner, who is “proud of little Ronnie whatever he does”, and his sister, a prim young lady who has just become a legal clerk of all things. “Ronnie must respect women,” she said, defensively, “they put food on his table don’t they?” Rocky paid a visit, a well-attired hustler in furs, knock-off Rolex and shades: “I been looking for a job for two years but there ain’t nothing around!” And Whitefolks dropped by, or rather he invited himself. As his name suggests, Whitefolks is a sore-thumb incongruity in the pimp world – a pink, fortysomething beergut in black jeans and torn sneakers, he looks like a roadie fallen on hard times. “I’m retired from pimping, so I can move into the entertainment business like Eminem,” he says, indignantly. “And my story’s better. Eminem’s trouble is, he can’t express himself.”

Come eight o’clock, the scene has returned somewhat to normal. Mob Deep’s “Murder Murder Kill Kill” plays on the stereo, battling the sound of Pimps Up Ho’s Down on the immense television, and the screeching cars and gunfire coming from the back room Playstation, where the kids are playing Grand Theft Auto. A few local teens smoke marijuana in a corner. There’s a sad woman in the armchair quietly necking beer from a brown paper bag and as the hookers clear the table, an infant scrapes around the filthy floor shooting everyone with a toy pistol “bang! bang!”


“Pimping is very political,” explains Ronnie, shooing the child at his feet. “It’s all about networking. Like you can give a nigger a call, say ‘how your ho’s doing down in Las Vegas?’, and he might say ‘they making $3000 a night, you need to bring your bitches down here’. If you don’t network, you don’t hear what’s going on.” The practice of roving around the country selling sex is a common pimp boast, (hence the “Cross-Country Pimp of the Year” award) – it panders to their sense of community and entrepreneurship. Few girls actually ever leave their hometowns, however, other than to go to the Players Ball, and then only if they can afford it.

“But the Bishop, he on another level, he got all the hook ups. He could give you a call, and you could get your own movie! He already got me playing the lead in a movie Snoop Dogg’s producing. We shooting in a couple of weeks in Miami.” Not that Ronnie can name the director or any of his co-stars. He hasn’t even seen the script. “I’ll read that when I get there.”

On cue the Bishop appears on screen in giant close-up, drawling like a grizzled drunk about unifying “this pimp shit” to a rabble of rapt admirers in a barber’s shop. Though he burbles hopelessly from one non-sequitur to the next, his audience nod in awe and salute him with cries of “Church! Church!” The Emperor’s new clothes are evidently green and gold.

“You see what I mean?” says Ronnie, as though his point has just been proved. “That’s what I’m talking about. Now, I know the Bishop. Whitefolks don’t, he ain’t even got no ho’s. But I know all them Church cats. Listen.” He plays me a “what’s up? Call me” message on his cellphone from Bishop’s right hand man, Minister Seymour. “See? So I fin to get the brother a pair of gators or something. Not because I have to, but because I respect him.”

Leaving aside his warped notion of respect – he respects women too, while sending them to screw a fleet of truckers every night – Ronnie has, within a few sentences, gone from spitting the Bishop’s name to owing him his huge acting debut and now to boasting about receiving an innocuous phone message from the man’s henchman. And he doesn’t care whether I have noticed that it doesn’t add up – he may not have noticed himself. The exaggeration I can accept as a congenital disorder and part of the whole pimp burlesque. When he happens to mention his vast collection of $7,000 mink hats, five houses, 50 pairs of gators and weekly earnings of $10,000, I let it slide – after all, pimps are supposed to show off, it’s their thing. But these glaring inconsistencies are much harder to stomach. Within a cup of coffee he will flit from “pimping is hard work” to “I don’t do shit all day, I send a ho to get my money” or from “I’m a family man” to “I ain’t married, they ain’t my kids.” As for what he’s up to next month, he is either shooting a movie in Miami, or selling his girls in Memphis, or Vegas, or, for that matter, all three at once. When I ask how he could possibly be simultaneously in Memphis and Miami, he retorts, “you see this car I got don’t you? I just drive between them.” It matters not that Memphis is 1000 miles from Miami and 600 miles from Chicago or that his shabby Cadillac has a back bumper held together with sellotape – Ronnie feels no need to defend his ridiculous claims, only to keep making them like some psychological tick.


This may be the cornerstone of pimping – forget the devilish charm with which pimps are rumoured to entwine their women, ‘game’ is often no more than an advanced case of braggerhea, the steady discharge of hollow boasts made with utter conviction and no regard for plausibility. It’s a confidence trick that works on certain prostitutes like hypnosis. And pimps too are hypnotised at some level. No one falls for the pimp myth more than pimps themselves.


“I got so many bitches it’s pathetic man, because they just love that 14K juice, see what I’m saying? Motherfuckers want to be like me but can’t nobody be like 14K man, I kept it real in the game for 20 years, in that order, man, because I am that nigger your mother warned you about, the nigger everybody’s talking about worldwide, pimpwide, playawide man. I walk like a pimp and talk like a playa, I’m all that shit…”

An exponent of ‘game’ at its most effluent and asinine, Fourteen K fell harder than most. He admits to being first drawn to this life by movies like The Mack (just as modern Mafiosi took their early cues from the Godfather), and now that he is “that nigger”, now that he has won Playa of the Year he couldn’t be happier, always grinning, whooping it up for the cameras and waving his silly goblet around – it’s a shame there’s no Jolliest Mack award. In a quieter moment, once the first froth of ‘game’ has died down, he owes his happiness to Church, and claims the Bishop as his personal mentor. “Man, the Archbishop taught me the game, that’s why I’m as cold as I am, man.”

This vision of pimping as a steeped tradition with apprenticeships and elders is a common delusion. Having compared the accounts of Fourteen K, Ronnie, Al Capone, Whitefolks, Scorpio and, erm, Dave – “but I call myself SuperDave because I’m kinda super and shit” – pimps seem to regard themselves as the torchbearers of an ancient wisdom, practitioners of the second oldest profession, a trade so fundamental that the whole world may be reduced to its binary ontology of pimps and ho’s. For instance, Ronnie informs me that the Times is pimping me. Capone insists that most men are pimped by their wives because they’re out earning while she stays at home. Dave calls the police the government’s ho’s. No one is safe.

The tradition has a code, of course, every club has its rules. Foremost is the 100% rule whereby a prostitute must surrender all of her money, not just a cut to her ‘daddy’ (a term of bitter irony considering the prevalence of sexual abuse in the childhoods of many prostitutes). In return the pimp commonly puts his girls in a house together where he covers their expenses and buys ‘whatever they need’. (Yet rarely do any girls own cars or apartments of their own. Even their wardrobes pale compared to those of their pimps).

A further founding principle is “no drugs” – pimps are often affronted by their association with common drug dealers who sully their profession. A bonafide card-holding pimp, it seems – and they really do have Famous Player membership cards, granted by the Bishop – bans his girls from so much as a joint while they work. “I want a hard-working ho,” says Fourteen K, “the bitch gotta give her money to me, not the dope man.”


Times may be changing, however, on issues of etiquette, such as whether a pimp should beat his girls or not. The Bishop boasted about routinely battering women well into the 1980s in his memoirs, “From Pimp Stick To Pulpit” but today, his pimp Grasshopper, Fourteen K, wouldn’t think of it. Or so he says. As a concession, perhaps, to social mores, or more likely the spotlight of the media, the fashion among modern pimps is to beat women on the sly and then deny it. Those who openly follow the Bishop’s example are scorned as ‘gorilla pimps’ – Dave is one such lying gorilla – as opposed to ‘gentle pimps’ like 14K, Scorpio and Ronnie who won’t even call his girls ‘bitch’ to their faces. As Fourteen K says, “you start beating on bitches, you giving pimping a black eye”.

Though pimps fight frequently – it is violence that underpins their world, as I was starkly reminded – they pay lip-service to a spirit of community. “If a nigger says ‘my bitch just left me man, I’m running low’, I’ll peel the nigger off a couple of hundred if he a true pimp,” says Capone, stretching credibility. In this fantasy, an inter-pimp dispute is settled by an orderly committee meeting. “With this card I can reach any pimp in the world,” he explains, “so if I got a problem, I take it to the major pimps and we vote on whether to get this man towed off our track.” In the finest pimp tradition, the girls do all the work. “We tell our girls, all combined, to chase his girls away.”

No doubt the Players Ball is intended to promote such pimp unity, but instead, it has the opposite effect. The awards breed tension, jealousy, bribery and plenty of snide gossip – pimps are a bitchy bunch. Ronnie bitches about Whitefolks, Whitefolks about Domination, Domination about Capone about Ronnie and everyone but Fourteen K hisses privately about Church, they resent the Bishop’s hegemony. When we visit Mister Kays, a favourite pimpwear outlet in the Chicago ghetto, Ronnie joins the bickering group at the front desk.


“What’s his name, Snoop Dogg came in the other week,” says Mister Kay, a chubby fast-talking Italian with a ponytail who might be plucked straight from a Spike Lee movie. “He had about 20 Church guys with him and they started stealing shoes. So we had to lock the shop up and search everyone.”

Ronnie shakes his head seriously. “Yeah, they’re disrespectful niggers. I don’t even fuck with Church no more.” He then picks out a pair of green and gold gators worth $950 – “I just get the Bishop something for his birthday, you know” – and starts begging Mister Kay for a loan.

As the big day nears and Ronnie’s expenses mount, his demands for remuneration become exhausting – always for the Bishop, of course, never himself. So I eventually arrange to meet the Bishop myself, with Ronnie’s introduction, at one of the many parties he holds for arriving pimps in the days before Ball. As Billy drives us all there, he dispenses his usual hectoring advice. “Now listen, you gotta be real respectful, because this ain’t just a party. This is the Bishop’s private house.”

I’ve heard tell of the Bishop’s house – in his prime, his toilet seats were made of clear glass and lined with $100 bills, the walls were bedecked in green and gold drapes, even his poodles were dyed in the colours. Today, however, we find Bishop in a pokey basement flat in a dishevelled, paint-chipped tenement, sat drunk on a sofa beside an addled old dear who might easily be in her 70s. A DJ plays some old soul in the corner but there is no room to dance, nor anyone to dance with other than 15 overdressed black men, dripping in cologne and sipping sparkling wine from Arthurian goblets encrusted with fake gems. In the tube-lit, adjoining kitchen, two fat women in tracksuits are tucking into tubs of leftover turkey. A toothless geriatric stands at the door, barking “Church! Church!”

Clearly too busy to talk, the Bishop palms me off to one of his helpers, an aggressive young follower in a bright pink suit who won’t hear a word until he has $2000 for access to his leader. I offer $200 in cash, which prompts a brief whispering huddle. Then the Bishop comes lumbering out of his stupor. “HBO paid me $50,000!” he snarls, setting off a chorus of righteous sycophancy that fills the room. (HBO refuses to take part in this story). As myself and the photographer are bustled out onto the freezing streets, the dandy bouncer in pink snaps “Church!” and slams the door. Whatever happened to room at the inn?

After a few minutes, Ronnie emerges from the party, no doubt planning our mugging even then. “I know you mad,” he says, “but whether you know it or not, you just been blessed. You just met one of the richest motherfuckers in the world! He richer than Donald Trump!”


This is the tragedy of Ronnie – he curses the Bishop in private but still bows and scrapes in his presence like a cap-doffing house slave. Every time he hands him an envelope, or a pair of $1000 shoes, he is paying a pimp, which as he well knows, is “what bitches is for”. Yet if he had the $20,000 for the $40 trophy he would surely pay. Just as the girls often need pimps for want of someone, anyone to believe in, Ronnie needs the Bishop and the whole pimp myth that he represents. Without the “billionaire” Bishop leaving him phone messages, Ronnie too has little left to cling to.

And Ronnie is broadly typical. So much as the armchair psychology of ‘he doth protest’ is valid, pimps scream ‘esteem issues’. For no one doth protest quite so much as a pimp, nor about so many things – wealth, fame, wits, toughness, appeal to women, anything in fact that comes to mind. And certainly, the self-loathing runs deep. According to what history exists on the subject, the first pimps were opportunistic slaves who thought to capitalise on the rape of their women by white masters. Ronnie now embodies that abuse in many ways. Like the slavemasters, he keeps black women as property, like the first pimps he still cashes in on their occasional rape and like the house slave he looks up to the master’s lily-white daughter as an object of unattainable beauty – which is why he has never pimped a white girl.

“Man white girls are too beautiful, they just finer than black girls. I know some white bitches want to get with me, too, but I might just fall in love with her, and that’s the worst thing you can do is fall in love with your bitch.”

Of his two girls – a paltry count, though few pimps have more than five – Gypsy is his ‘bottom bitch’ (a compliment). It was Gypsy who first turned Ronnie into a pimp by offering to whore for him five years ago. “Yeah, I respect Gypsy, I know she’ll never leave me so I got a ho for the rest of my life. But it ain’t love. She could leave me tomorrow and take the kids with her, they ain’t mine anyway.”

The stories Ronnie tells about Gypsy are harrowing, though again he could be bragging – every pimp has his far-fetched tales of hooker devotion. The Bishop boasts of the time one of his girl’s was shot, and still later that night, when patched up by the hospital, she insisted on returning to her beat to earn daddy’s money. Ronnie’s version has Gypsy getting her face smashed with a fire extinguisher by another demented john and again, insisting on going back to work the same night. “I said, shit, with that face you going to scare away the customers! But you know, it was cool, because some of her regulars just gave her money because they felt sorry for her.”

Gypsy herself claims to have never been hurt on the job. She says she likes her work, and is perfectly happy to be Ronnie’s whore. Every night she puts the dinner on, the kids to bed and then her life on the line before she gives her man her money and she is adamant, “there’s nothing else I want to do more than make my daddy shine”. The daughter of a prostitute herself, Gypsy grew up watching her mother take a beating from a succession of gorilla pimps, so she avoided ‘the game’ for years, working various low-grade office jobs. “But I wanted to see more of life,” she says, “I wanted to be in the light, I wanted that fast money.” Why then, does she give her hard-earned to a pimp?

“Because everyone needs protection. And I couldn’t take care of my money, I would spend it as fast as I got it, so I needed a pimp for financial management.” But Ronnie spends it on goblets and mink coats. “That’s right. Ain’t nobody can provide for my man like I can.” Surely though, if you were independent… “No, I got no time for renegades. When I see a girl on my track and she don’t got a pimp, I chase her off myself. You got to have management or you taking a pimp’s money, and that ain’t right.” To paraphrase Arthur Miller, “there is no power on earth that can break the grip of a woman with her hands on her own throat”.

Last week, Gypsy found a girlfriend in Aphrodite, a fellow prostitute who would show up for work bearing the bruises of her latest beating from Pimp Dave, an inveterate gorilla. So one night Gypsy brought her home to Ronnie’s fold, or to use the jargon, Ronnie “bumped” Dave’s prostitute. (They talk also of girls choosing their pimps rather than the other way around but choice is a tenuous concept in the world of street prostitution.) Bumping is often a testing time for all concerned, although so far, Aphrodite’s move has gone ahead without incident. “Some pimps develop feelings for a girl and that’s where the problems start,” says Ronnie. “But Dave, he cool. He a gorilla but he knows ain’t no bitch ever come between two pimps.” Remarkably,Dave is the same. He shrugs, “that’s just the way it goes. I know I bumped a few bitches in my time.”

For Aphrodite, moving to Ronnie’s has been a minor blessing in a life so riddled with scars. Abused by her stepfather, who shot her mother, not long before she herself shot her sister in a dispute over her grandmother, Aphrodite left home at 12 and was a prostitute by 16. She is now 28. She has avoided a serious drug problem to date, instead she betrays her dysfunction by wearing vampire teeth and flinching when she finds sitcoms or soaps on the television. “They’re always hugging and kissing on those programs, it makes me feel sick.”

Now, Gypsy, Aphrodite and Ronnie live together as a loose family, with six children, all from Gypsy’s previous marriages. The girls call each other ‘wife-in-laws’ though neither is married to Ronnie, nor do they share an intimate relationship with him – outside of work, the girls care not for men but each other. As Ronnie says, ‘a lotta ho’s on that lesbian shit’. All of which leaves the pimp leading an oddly sexless life. So much for the mythical potency of the sharp-dressed hustler who could turn any square girl out – according to his pimp principles, Ronnie cannot have sex with anyone unless he gets paid, “otherwise it’s disrespectful to my girls”, so he has been chaste for over 6 months. “No, a year. I don’t know, a long time anyway,” he shrugs. “But pimping ain’t about sex. Pimping’s about money.”

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Come the day of the Ball, having successfully menaced us out of $1000, Ronnie is in much higher spirits – at least the Bishop’s shoes are paid for. All morning he has been strutting around in his pumpkin suit, posing in front of mirrors on his cellphone. “What time you turning up? Yeah, I got the limo booked, the whole shit.” When the removal men arrive to wrestle his sofa down the stairs for a good hour, Ronnie can’t resist rehearsing his ‘game’ for tonight.

He asks the removal men, “you know you in the house of the number one pimp in Chicago right now?” They just grunt from beneath the sofa: “left a bit, now tip up your end…”

“Yeah I send a bitch to go get my money,” continues Ronnie. “You see the ING in pimping? That stands for ‘I’m not going’. Bitch got to pay if she with me, in that order. Because a real man don’t pay for it, he gets paid.”

The sofa corner is stuck on the hinge. “Wait, wait, back up a minute…”

Moments later, Ronnie is looking at his watch and flapping. “I ain’t got time for this sofa shit. It’s what – two already? I got to get my hair done, my face done, my nails, I got to get my shoes waxed…” It’s hard being a real man. The manicure bills alone.

As Ronnie’s rentalimo pulls up, the first members of the public have begun to gather at the gates. It’s a bleak venue, the East of the Ryan motel. A rundown yellow brick building with a broken sign in a bustling ghetto high street, it seems better suited to bingo night. Nevertheless, about 30 enthusiasts between 11 and 30 years old wait in the biting cold to catch sight of this annual pimp migration, joined by cameras, video and still, attached to local Chicago newspapers and minor web TV networks (no CNN or ABC as promised). They stalk the arriving cars in huddles, as each one disgorges its preposterously parcelled thugs, flanked by frequently matching women. Snoop Dogg’s stretched Hummer was a highlight that set the flashbulbs popping, and the Bishop too. Curiously, when the Bishop arrived at the heart of a mob of Church heavies, they all started chanting “Church on the move! Church on the move!” in eerie chain gang unison.

Billy holds the door open and the girls emerge first, each wearing a matching mauve outfit and clutching a white teddy bear and a single red rose. Then Ronnie steps out followed by Billy’s drunken girlfriend. No one takes any pictures. “Now don’t be telling anyone that you with me, OK?” he says. “And stay away from Church cats, because they’ll throw your ass out. And don’t be talking to no women because they all ho’s. Niggers be thinking you trying to bump ’em. And no pictures.”

Duly cowed by a barrage of warnings, and with last night’s robbery firmly in mind, I finally enter the Famous Players Ball, 2002, and head straight for the bar. It seems the safest place – at the back of the hall, separated from the Bishop on stage by a busy dancefloor and a few rows of tables and chairs.

At a glance, the room is mostly male, furry and loud. An assemblage of pimps and wannabes, who swagger about congratulating each other on their outfits – white fur is particularly in this year – and cast around for girls to bump, idling at the trinket stands that line the perimeter. There’s Scorpio checking out the plastic goblets for sale, while his girls examine the plastic earrings next door. Most of the men are up the front, gathered at the Bishop’s feet, as he garbles into the microphone and hands out trophies. Their girls, meanwhile, mostly sit at the tables – decked in green, in tribute to the Bishop – eating chicken wings and sipping cocktails. For many girls the Players Ball is a huge treat, a reward for a hard year’s work.

As huge and lucrative as prostitution is in the United States, and as global as these pimps claim to be, the Players Ball is unmistakeably small-time and provincial, right down to the paper plates of fried chicken. It’s an anachronism, this celebration of street prostitution, in a market that has largely veered away from the street to escort agencies, websites and otherwise. Yet the Pimp of the Year – Kenny Red, from Ohio – has only two prostitutes. It isn’t his lack of hookers, however, that makes him a surprise winner. “I’m first nigger in history to take the trophy out of Chicago!” he yells.

Kenny Red denies paying the Bishop any kind of bribe or lavish birthday present – but we can safely assume it was more than a pair of shoes. For the green and gold gators, Ronnie is awarded the third runner up prize and he seems disappointed, even though it’s his first ever award at a Players Ball after five years of attendance. Billy is left to guard the trophy as Ronnie skulks around the room looking for Aphrodite, who has apparently been throwing up in the ladies toilets. It’s time to go home.