Three weeks ago, Charles Larocco, the embattled King of Bootleggers, found himself in a Brooklyn holding cell waiting— for the third time in 30 months— to be arraigned on federal criminal charges. Just like in June 1996 and May 1997, the 42-year-old had been arrested that late-January afternoon by an all-too-familiar posse of agents from the U.S. Customs Service. Among these veteran New York investigators, Charlie was somewhat of a legend, only the second guy they had ever arrested three times for the same crime— in this case, the illegal sale of bootleg CDs featuring groups like Nirvana and Garbage.

Until January 27, when Charlie hit the trifecta, the three-arrest record was held solely by some Queens recidivist who could not fight the overwhelming urge to manufacture crack pipes.

But it seems that LaRocco— the legendary "Mr. Big" of bootlegging circles— will not, or cannot, stop selling illegal CDs. His multimillion dollar operation, which manufactured and sold bootleg albums to many New York City record shops and hundreds of retailers nationwide, has been crippled by federal investigators, so LaRocco— who has been free on bail— recently had to test a new distribution tool. But he was quickly collared again, this time in cyberspace on one of the Web's most popular sites.

Facing several years in prison, LaRocco appeared defiant— and also a bit delusional— during three Voiceinterviews last week. Asked about his January bust, the slender and soft-spoken LaRocco said, "I was happy it happened. Because to me it's like an exciting adventure. Because when you feel you did nothing wrong and they're coming and accosting you under those circumstances, I feel I got nothing to lose."

LaRocco actually spoke fondly of his latest legal scrape. "I mean, when I go in the cell with all these drug dealers, it's an experience for me." While waiting to be arraigned, he showed off his Latin music chops to two impressed DEA detainees. When his cellmates then asked about his case, Charlie lied, claiming that his charges were rather serious. "Of course, I'm embarrassed to tell them all I'm in there for is CDs."

An ascetic character who hews to a weird, quotidian schedule, LaRocco has already pleaded guilty to charges filed in connection with the first two arrests. But he scoffs at the notion that he will actually be punished for those crimes, though federal guidelines call for a prison term of 30 to 37 months when he is sentenced on March 19. He expects investigators to soon admit they were wrong about him and return the nearly 1 million bootleg CDs. The albums, seized from two Queens warehouses in 1996, are now being stored in a Customs Service depot. For Charlie, it is as if a member of the family has been held hostage for more than two years.

As they had done twice before, Customs agents traveled to Valley Stream, where they arrived in the early afternoon at the modest ranch home LaRocco shares with his 82-year-old mother. They were again carrying an arrest warrant for Charlie and a search warrant for the premises. But since both Luna LaRocco and her son suffer from sleep disorders and live the lobster shift, they had to be rousted awake by the raiding party. As agents took Charlie from the house, he had a parting message for his mother, who was enduring the third court- ordered raid of her home. "Mom," he whispered, "watch 'em so they don't steal anything."

As it turned out, the 1999 canvass netted little, unlike a 1996 search that turned up $490,000 in cash. Charlie had hidden wads everywhere: $4900 in the microwave, $46,620 in a credenza, $193,600 in the laundry hamper, even $220 in the cookie jar. The rubber bands on some stashes were dry and brittle, leading investigators to theorize that Charlie— who suffers from short-term memory loss as a result of a serious car accident— may have forgotten where he once hid the loot. He does not trust banks, LaRocco explained, because "If something's not in my possession, I'm not comfortable. I need to be in control of everything."

On his first two trips through the system, LaRocco had been charged with distributing large caches of CDs featuring live performances by artists like Jimi Hendrix and Pearl Jam. When it came to bootleggers, Charlie was the recording industry's chief nemesis, No. 1 with a bullet. After analyzing LaRocco's meticulous business records— which were kept in small spiral notebooks and on pieces of cardboard— federal investigators were able to quantify the remarkable scope of Charlie's business. Customs officials figured LaRocco earned more than $15 million selling swag from 1990 up until his first arrest in mid 1996. And that figure would have been higher, a former LaRocco associate said, if a "placid" and "very generous" Charlie had aggressively pursued unpaid bills. This assertion is supported by LaRocco's own financial records, which listed many accounts payable.

And Charlie was making this mountain of cash even though he did not like rock and roll.

LaRocco prefers gospel quartets and old r&b to Smashing Pumpkins and Bruce Springsteen. In fact, when he was younger and his peers were plugging in, Charlie sang tenor in an a cappella group on the Lower East Side, where Charles Cyril LaRocco grew up the youngest of three children on Monroe Street. This harmonizing was an "anachronistic sound for the time," he recently recalled. But while his customers' tastes may have run counter to his own, LaRocco never let that affect his bootleg operation. Charlie understood that Marilyn Manson, not the Marvelletes, moved product.

When he starts evangelizing about his unfair treatment at the government's hands, LaRocco reveals the focused, obsessive side that allowed him to build the nation's largest bootlegging business. A former criminal associate said it was that drive— and a paucity of career alternatives— that kept LaRocco peddling illegal CDs. "This is what he knows how to do," said the source, who himself was convicted in a related smuggling case.

Amazingly, LaRocco has operated essentially as a one-man enterprise. Using a network of U.S. contacts, investigators said, LaRocco would secure tapes of live concerts or recording studio sessions by headline acts. He would then have a variety of production facilities in Europe— including well-known firms like Swinging Pig and Why Not— produce CDs of these performances. The records were then shipped to New York, where Charlie packed them into jewel boxes carrying four-color insert cards, many of which he designed. The finished product was then distributed to LaRocco's domestic customers, who paid around $10 for CDs that would later retail for around $25 to $30."For what he was doing, he could have been written up in Entrepreneur Magazine," said Edward Dempsey, a Customs Service group supervisor.

And like any accomplished smuggler, Charlie dealt only in cash and postal money orders. Along with several personal aliases (apparently including "Pookie"), he operated under an array of business names, none of which were incorporated or registered in New York State. LaRocco used a series of drop boxes to receive mail and filed fraudulent Customs declarations to sneak bootlegs into the country. He never paid taxes and used a series of phony social security numbers. When investigators recorded some of his telephone conversations, he spoke in code, referring to CDs as "magazines." While he has claimed to have been unaware that selling bootlegs was illegal, LaRocco sure operated as if he had something to hide.

For LaRocco, the ongoing law enforcement scrutiny has been a major annoyance and a disruption to his regular routine. That regimen basically revolves around his hunt for records at tag and garage sales and his daily postmidnight trips into Manhattan for bicycle rides and three-mile runs. "It's like an oxymoron, but I strive for contentment. I'm content with the way things are. So I just look for no changes. I got great equilibrium." That balance, however, was thrown off again last month.

Though on bail and awaiting sentencing for his previous bootlegging activity, LaRocco was nabbed in a first-of-its-kind Internet sting launched by World Trade Center–based Customs agents. LaRocco was caught selling bootlegs on eBay, the popular online auction site. Aided by the anti-piracy unit of the Recording Industry Association of America (RIAA) and a confidential witness, Customs agents successfully bid for Byrds and Beach Boys albums offered for sale by LaRocco, who is known by several eBay handles, including "groupsound" and "harmonysound." Investigators presented Roger McGuinn with the Byrds CD— a recording of a 1978 reunion show in San Francisco— and the group's founder announced that those ringing Rickenbackers were recorded without permission.

Together, the two winning eBay bids cost Uncle Sam $96. In an additional $100 transaction conducted via e-mail, LaRocco also sold the federal source four other bootlegs, including Alice in Chains and Tool performances. Normally, a measly $196 illegal sale would not be worth the effort of Customs agents and federal prosecutors. But when it comes to LaRocco, the government has a zero-tolerance policy in light of Charlie's lengthy pirate pedigree.

Strangely, the great majority of items LaRocco has sold on eBay appear legitimate, like Al Green and Sly Stone singles and a variety of old Stax 45s. Feedback posted from nearly 100 LaRocco customers is almost uniformly positive. "Five *****'s Charlie!" and "Charlie's a fab dealer" are typical examples of such praise. It is unclear why, among all these old r&b and soul offerings, LaRocco decided to chance slipping in some stray bootlegs, a decision that could lead to more jail time and revocation of his current bail package. But for Charlie, jail is just not an option (as if he has a choice): "There's no possibility of that because there was no wrongdoing on my part." This, of course, is coming from a guy who stood before a magistrate last year and copped to three felony counts. When his sentencing day arrives, LaRocco is sure the judge will realize the case against him is "a joke."

LaRocco believes that the federal bootlegging statute enacted in late 1994 as part of the General Agreement on Tariffs and Trade (GATT) is unconstitutional and will eventually be overturned. Along with two criminal defense attorneys, LaRocco has also hired a copyright lawyer and an intellectual property expert to research possible legal challenges to the bootlegging law. Of course, along with already pleading guilty to that statute, LaRocco also admitted that he violated separate smuggling and currency reporting laws. And nobody's arguing that those sections of the federal criminal code are particularly flimsy.

As LaRocco finances a multiple-member legal team, Customs agents are left to wonder whether the bootlegger successfully hid large sums of money earned by his illegal operation (in places other than the hamper or cookie jar). Investigators believe that Charlie made far too much money to have spent most or all of it. "I live like an impoverished guy," said LaRocco, who added that he has taken one vacation in his life. And that was only a brief record-buying expedition down South in 1976. "I don't need an escape from anything," he said, "because I'm content with the environment that I'm in."

As he awaits exoneration, LaRocco busies himself with a strange nocturnal schedule. Because he cannot sleep at night, Charlie naps during the day and heads into Manhattan near midnight. He drives a 1996 Isuzu Trooper because his 1992 Isuzu Trooper was seized by Customs agents. In the back of the truck is Charlie's trusty bicycle. Nowadays he is riding a Raleigh R-40, but that could change momentarily, since LaRocco said he has had 13 bikes stolen in the past two years. There is something about a bicycle chained to a No Parking sign at 4 a.m. that attracts those with a larcenous heart.

He rarely has a route planned for his two-wheeler, he just goes "where my bicycle takes me." Often he'll bike someplace, lock up his wheels, and go for his nightly three-mile run. Charlie can be found crossing the Triborough Bridge, running on the Coney Island boardwalk, or even jogging up and down Eighth Avenue. With the terrain changing nightly, how does he know when he's run three miles? Well, he counts the number of strides he takes. For every 700 times Charlie's New Balance 875s hit the ground, he has traveled a mile. Twenty-one hundred paces, and three miles have gone by.

Certain days of the week have their own rigid schedules. On Monday nights, Charlie heads for an Avenue C club to watch a favorite honky-tonk band. On Tuesdays, he drives his mother into Little Italy for dinner on Mulberry Street (usually Pellegrino's). He then drives back to Valley Stream, drops her off at home, and then returns to Manhattan for some biking and jogging.

But for Charlie, his schedule will not be whole again until he can start selling a mountain of bootlegs. "I don't regret doing anything at all. I would do it again. I'm just gonna wait for the government to say, 'Okay, we made a mistake. Continue operating the way you were operating.' It's only a matter of time before they realize that I didn't do anything wrong."

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