In 1988, Georgetown-educated attorney Dwain Kyles was solidly entrenched as a member of Chicago's black professional class. He and his wife, another lawyer, owned a condo in an up-and-coming neighborhood just south of the Loop. He'd worked for Mayor Harold Washington and was close with the family of Rev. Jesse Jackson.

His low-key, earnest style and quick mind won him friends and business prospects, as did his willingness to supply money, clothes and free legal advice to those in need.

"Someone would call Dwain from Operation Push, from the Urban League, and say so-and-so needs some advice, so-and-so needs help," said Abe Thompson, a radio-station owner who has known Kyles for years. "Someone wants to have an event, and they don't have a lot of money... And Dwain would help them."

At the same time, Kyles, the son of a prominent Memphis civil rights leader, was involved in an unusual business venture for someone in his position: Running a nightclub.

The club would later become E2, where 21 people were trampled to death in February 2003. Kyles was charged with involuntary manslaughter in the wake of the tragedy. His trial is scheduled to begin today.

Even before the E2 stampede, though, there were signs that Kyles was something more than the dapper attorney and community activist that he appeared to be.

Federal agents caught a former director of the club with 18 kilograms of cocaine in a downtown hotel. E2's manager was a man who'd done prison time for killing a patron at another bar. Kyles defaulted on his mortgage, fell into tax trouble with the state and federal governments, and was censured for attorney misconduct. Patrons at Kyles' club sued repeatedly, alleging security problems that foreshadowed the 2003 disaster.

Kyles could not be reached for comment on this article.

Born in Chicago, Kyles spent most of his childhood in Memphis. His father, Rev. Samuel "Billy" Kyles, is the man Rev. Martin Luther King Jr. was going to visit on the evening he was assassinated in 1968. The elder Kyles also serves on the board of Jesse Jackson's Rainbow/PUSH Coalition.

From a young age, Kyles settled on a career in law or politics, said Rev. James L. Netters, who knows the family. Kyles volunteered on political campaigns and for his father's civil rights efforts.

"He was very studious, very obedient, very respectful," said Netters. "He had his mind set on what he wanted to do. I always admired him for being ambitious and for how he went about getting what he wanted. He was very mannerable, but persistent."

Kyles left Tennessee to attend Lake Forest College, in the suburbs north of Chicago. After graduating from Georgetown University Law Center in 1979, Kyles accepted a job at Johnson Products Co., the Chicago-based maker of black hair-care products.

Marilyn Cason, then the company's general counsel, hired Kyles on the advice of the company founder, George Johnson. Johnson's son had gone to Lake Forest College with Kyles and the two had become friendly.

"The Johnsons knew him and liked him a lot," Cason said.

Cason said Kyles' legal skills were much like those of any recent law school graduate. His personality made an impression, though.

"He seemed very gentle, kind, well brought up. He was interested in being with a black company in particular," she said.

It was a heady time for Johnson Products, and for Kyles. The company was for years the lone sponsor of the Soul Train television show, and Michael Jordan was appearing in Johnson ads. Kyles, a lifelong basketball fan who still spent time on the courts at a Hyde Park gym, was excited.

"The excitement of that world drew his interest," said Cason. "He was sort of fascinated with that side of the world, entertainment law and all that."

In 1983 Harold Washington was elected mayor of Chicago. Kyles left Johnson Products and took a job in the city's economic development office.

"He was a very dedicated guy when he worked in government," said Al Johnson, who hired Kyles. "He gave much more than eight hours a day."

Around that time, Kyles talked often about starting a business that would provide a good environment for people in the black community to gather, said Thompson.

"He thought that if he had a restaurant, people could meet, exchange ideas, and bring their families," said Thompson.

In January 1986, Kyles filed incorporation papers for La Mirage All Nite Studio, a juice bar.

Shortly thereafter, Kyles changed the club's theme. He renamed it as Heroes, billing it as "Chicago's unique disco eatery." He also applied for a liquor license.

"I had no real appreciation for what I was getting myself into," Kyles wrote later in court documents.

In June, 1988, he married Theresa Cropper, whom he met when they both attended law school in Washington, D.C.

Six months after the wedding, their first child was born.

A second son, who was born needing a heart transplant, followed him in 1990. The couple's health insurance would not cover the procedure, and they mounted a high-profile effort to raise money. Stevie Wonder, for whom Cropper had worked, played a benefit concert.

Meanwhile, the club was becoming known as a prominent gathering spot in the black community. But there was another side to Kyles' business.

He and the club have been associated with two men who have run afoul of the law.

Kyles incorporated the club with Chicagoan Marc Wells.

In August 1988, a little more than two years after Kyles and Wells joined forces, federal agents arrested Wells at a South Loop hotel.

An informant had called the FBI and told agents that a man named Marc was registered at the hotel, and carrying a substantial amount of cocaine, court records said.

Federal agents staked out Wells' room and caught him leaving with a suitcase containing 18 kilograms of cocaine an amount worth millions of dollars, according to court records.

Wells, who had no criminal record at the time he incorporated La Mirage with Kyles, pleaded guilty to drug charges and was sentenced to a federal prison term.

He was not listed as an officer on the club's state filings when he was arrested. Asked if he was involved in drug dealing while he served as a director of the club, Wells declined to comment.

Another Kyles acquaintance, Calvin Hollins, also faced criminal charges in the 1980s.

Hollins, a former Cook County sheriff's deputy, shot and killed a patron of the Streeterville bar he was managing in 1984.

He was charged with murder and convicted of manslaughter in 1990. The same year, Kyles wrote a judge urging leniency for Hollins: "Mr. Hollins and I are partners in one of Chicago's largest restaurants and sports bar... He both operates and manages our facility."

Kyles' statement was an eye-opener for two reasons. Hollins had never been listed as a shareholder on documents filed with the Illinois Liquor Control Commission. And, as a convicted felon, Hollins was not allowed to have an interest in a tavern.

Hollins' sentence was later commuted, and documents indicate his involvement with the club continued. City officials found his business cards on the premises after the stampede, according to public records. And in a complaint filed July 11, 2004, the Daley administration accused Hollins of having an illegal interest in the club and sought to revoke E2's liquor license.

Public records show the bar struggled financially, too.

In 1988, a construction contractor alleged that Kyles, his partners and the bar had failed to pay a $95,304 bill and placed a lien on Hero's.

Illinois state tax officials placed a $14,413 lien on Kyles' company in 1990, and the IRS weighed in with allegations about unpaid taxes, too.

In 1997, Kyles and the club paid a $20,000 settlement to a woman who claimed she was injured there.

The club had hosted a rap contest called Soul Explosion, the lawsuit said. Members of warring gangs were allowed into the club, which lacked the proper security arrangements and emergency exits, according to court papers. A riot broke out, and the woman, Debra Cobb, was trampled and severely injured, the lawsuit said.

That same year, Kyles was charged with battery. The case was eventually dismissed, and no details about the allegations against him are available.

Also in 1997, state bar regulators reprimanded him for misconduct.

Kyles illegally threatened criminal charges to obtain an advantage in a civil case, issued an inaccurate press release, and corresponded directly with his opponents in the case, even though they were represented by an attorney, according to state records.

And in 1999, Cropper filed for divorce. The couple had been living separately for two years, court papers said.

Kyles' attorney, Vickie L. Pasley, said the divorce was amicable.

"He's an extremely devoted father. Both parties are focused on their children," she said. "Representing him on the divorce was quite pleasurable, as divorces go."

But Ralla Klepak, who represented Cropper, disagreed.

"They didn't communicate with each other at all," said Klepak. "It was pleasant because they didn't communicate with each other."

The divorce agreement gave the interest in the club that would later become E2 to Kyles.

Klepak said the club was not making money. "He was functioning on a cash basis," she said. "If this were to be subject to scrutiny during an IRS audit, I could see there wasn't a good job of accounting for things."

Also in 1999, a dispute broke out between club patrons, and a woman was beaten and tossed unconscious outside the club's side door by employees, according to documents in the lawsuit she later filed.

Arbitrators awarded the plaintiff, Inecia Sneed, $9,000.

In 2000, Kyles remade the nightspot into a downstairs restaurant, Epitome, and an upstairs nightclub, E2. The building, lavishly decorated with marble pillars and plush carpeting, became popular with upscale blacks. Politicians held fundraisers at the restaurant, and civic groups often met there.

And the club served as a first performance for many Chicago artists.

"It's basically been a staple in the black community as far as a place for people to throw parties," said music producer Steve "Silk" Hurley. "It's a place in history for all forms of black music."

Kyles was a hands-on owner.

"He'd be there, asking if you needed anything. He would clean up a table if it was dirty," said Thompson. "He wouldn't go around saying, 'Hi, I'm the owner.' Most people probably thought he was the maitre 'd or a guy waiting on tables."

Problems at the club mounted, though.

A patron sued in 2000, claiming security guards allowed a group of drunks at the club to hit him on the head with champagne bottles, drag him out of the building and continue to beat him on the street.

The same year, another clubgoer sued, alleging E2 security workers had beaten him and a friend with flashlights and portable radios.

In 2001, employees beat, strip-searched and illegally detained two valet parkers working for the club, according to the lawsuit they later filed.

And in January 2003, a woman injured in a crash on the Dan Ryan Expressway also sued the club. The crash was caused by a motorist who had been drinking at the club and then drove south in the northbound lanes of the highway, court papers said.

Questions about the club's security and fire exits persisted until the early morning hours of Feb. 17, 2003, when bouncers used pepper spray to quell a disturbance in the overcrowded space.

Scores of people were jammed in a narrow stairwell and suffocated beneath the crush of patrons trying to escape the club. More than four dozen were injured, and 21 died.

Cook County State's Attorney Richard Devine, who brought charges against Kyles and three others, said the disaster could have been prevented.

"These four men knew that this was a dangerous environment to jam five times as many people as could safely be housed into the second floor of this club," Devine said. "The crowded conditions they allowed in this club were simply a disaster waiting to happen."

Those who know Kyles say the stampede and its aftermath devastated him.

"When he thinks about that, he can't even express it," Thompson said. "His boys are close to the age," of many who died at E2.

Reconciling Kyles' personality with the club's troubled history is a difficult thing, even for those who know him well.

"There are people who get caught up in things," Thompson said, "and by time they figure out it wasn't such a smart thing to do, it's too late."

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