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Henry Leon Harris, a former El Rukn “general” and star witness in the government’s massive case against the gang, had just completed testifying one summer evening in 1991 when a paralegal in the U.S. Attorney’s Office caught his eye.

Interceding on the imprisoned Harris’ behalf, Assistant U.S. Atty. William Hogan Jr. approached a co-worker of the paralegal, indicated Harris’ attraction and asked her to find out if the woman would accept Harris’ telephone calls from jail.

Upset, the co-worker said she told Hogan, “Absolutely not.” But later that same evening Hogan came up to her again and tried to introduce Harris. The co-worker immediately reported the incident to her supervisor.

Last week, in throwing out seven El Rukn convictions because of government misconduct, U.S. District Judge Marvin Aspen pointed to that incident of poor judgment as perhaps the best example of the lengths Hogan, the chief Rukn prosecutor, “would go to keep his witnesses happy.”

And the government’s successful dismantling of the notorious South Side street gang is threatening to fall apart now that three judges have ordered retrials for 13 Rukn defendants. More judges could follow suit.

There is no simple explanation for what went wrong.

Interviews with more than a dozen former and current prosecutors, as well as defense lawyers for El Rukn gang members, suggest an incendiary mix that included an overly aggressive prosecutor, a clash of personalities, human frailty, a breakdown in supervision and what some believe was a sense of arrogance pervading an office that had racked up a string of impressive courtroom victories since the mid-1970s.

“No one seriously questioned how the El Rukn prosecution was to be handled. They began to lose perspective,” said a former federal prosecutor now in private practice.

Some say the scandal has taken on the outlines of a Greek tragedy.

“It is full of tremendous emotions and powerful people and the clash of ideas and human weaknesses,” said John Smietanka, the U.S. attorney from Grand Rapids, Mich., who was brought in to oversee the Rukn prosecutions when the controversy heated up last December. “You can’t view this as good and evil clashing. Some people may feel vindicated, but I think they should all feel sad.”

To ensure the continued cooperation of Harris and several other high-ranking Rukns, Aspen concluded, Hogan and other government personnel covered up drug use by key prosecution witnesses in jail; sex in federal offices between Rukn cooperators and their wives or girlfriends; lax security that allowed them to smuggle in drugs; so many long-distance telephone calls top supervisors complained about the expense; and other improper favors.

Hogan has denied wrongdoing, including trying to arrange for the paralegal to call Harris. He is now on administrative leave with pay until the Justice Department completes an investigation.

Critics say the single-minded determination that propelled Hogan to effectively wipe out El Rukn may have also led him to lose sight of a prosecutor’s ultimate objective: justice, and not necessarily convictions.

From all accounts, Hogan 42, was a skilled, veteran trial lawyer. He had dedicated four years to eradicating a gang some have likened to Al Capone’s for sheer brute violence.

But in pursuit of that lofty goal, three judges have agreed, the government broke rules, shaded the truth and manipulated testimony as a result of what Aspen called Hogan’s “well-meant but misguided sense of justice.”

Some former and current prosecutors think Hogan has gotten an unfair rap. If anything, they said, Hogan was stretched too thin and just may have ignored or simply missed things because he was overwhelmed by the workload.

Under great pressure, Hogan worked 12 to 16 hours a day, often seven days a week, to organize the massive case, bring the 2-inch-thick mega-indictment, persuade six top Rukn leaders to provide crucial testimony and then personally lead the prosecution in five of the seven trials, one after another.

Incredibly, in the single biggest indictment in the history of the Northern District of Illinois-65 alleged Rukn members and associates were charged-Hogan was allowed to lead the case with little supervision, assisted generally by far-less experienced prosecutors.

Sources said that in the crush of trial activity, Hogan sought help by personally asking other veteran members of the office whether they could assist him in the Rukn prosecution. No one volunteered because of their own responsibilities.

During summer 1991, Hogan left one Rukn trial early to begin prosecuting another one while a third one took place at the same time. “It was chaos,” said a knowledgeable observer.

A former federal prosecutor blamed an unfortunate combination of facts and personalities: a single-minded prosecutor going after a vicious street gang, using zealous, aggressive tactics that strained his relationship with each of the three judges.

He noted that Aspen was upset at the start with the size of the indictment and the initial resistance of prosecutors to break the case into smaller trials.

“Bill was aggressive in defending that, so from the start he and Aspen got off to a bad beginning,” the former prosecutor said. He also noted that Hogan’s style “doesn’t play well with every judge.”

Another former insider faulted office higher-ups for failing to see the need in this case to establish restrictive guidelines on how to handle the manipulative Rukn witnesses.

Critics said former U.S. Atty. Fred Foreman, who headed the office during the Rukn trials but resigned after former President George Bush’s election defeat, promoted a win-at-all-costs mentality in the office.

At a going-away party early this year for former First Assistant U.S. Atty. Thomas Durkin, Foreman told the crowd he had extracted one promise from Durkin before appointing him: Don’t lose any high-profile cases.

Actually, contend veteran prosecutors, there wasn’t a win-at-all-costs mentality. But they conceded Foreman didn’t emphasize enough the need to do the right thing.

Aspen’s decision last week was the biggest blow yet for the U.S. Attorney’s Office in Chicago in this unprecedented scandal. Some in the office had hoped he would break with previous rulings of U.S. District Judges James Holderman and Suzanne Conlon and find the level of misconduct did not justify overturning the convictions. But Aspen blasted the government and ordered retrials for the highest-profile defendant in the entire case, former Chicago businessman Noah Robinson, and six of the gang’s allegedly most murderous members.

Rukn defense attorneys contend the government relied excessively on Harris and five other former Rukn generals, lifelong criminals, murderers and drug dealers who became the linchpin of the prosecution case.

In such an enormous case, the attorneys said, prosecutors felt intense pressure to keep the imprisoned cooperators satisfied.

In his ruling, Aspen said Hogan, “no doubt enticed by the prospect of convicting some of the most notorious malefactors in Chicago history,” curried favor with the ex-gang generals “to ensure continued and favorable cooperation.”

The witnesses, hopeful of winning more lenient prison terms and willing to lie, “figured out what the government wanted to hear and fed it to them,” said Peter Schmiedel, a lawyer from the Conlon trial. And prosecutors knew of the deception and in some cases deliberately concealed the lies, defense lawyers said.

Hogan went to great lengths to convince juries that Harris was a reformed man who had been religiously converted, read the Koran daily and regretted his criminal misdeeds, the lawyers said.

But it was bunk, and Hogan, after spending countless hours with Harris, knew that, they contended.

“They brought a wolf into the courtroom in sheep’s clothing,” said attorney Donald Young, who defended a cocaine-supplier suspect in one Rukn trial. “Over time the wolf finally showed itself.”

Working thousands of hours together transcribing tapes and preparing the case, government employees became too friendly with the cooperating Rukn witnesses, compromising their judgment, defense lawyers said.

They threw Harris birthday parties, gave him presents and other unreported benefits. Harris thought so much of Hogan he listed him in his will as the second-in-line beneficiary, behind only his mother, in case of his death.

“In Harris’ mind, his mother came first and then Hogan,” Young said.