Howard Medley, once among City Hall’s most influential political operators, slips through the lobby of his Hyde Park apartment building looking for a pay phone.

“I got to watch what I say on my phone,” Medley mutters. “It’s probably tapped. I want to call my lawyer. Ah, forget the phone call. I’ll make it another time. Let’s have lunch.”

It’s sort of sad to see him slithering about talking softly. Men like Medley should be bodacious and loud–the way Medley used to be.

By several accounts–particularly his own–Medley, 62, used to be one of the most powerful black men in the Democratic machine. He raised thousands of dollars in campaign contributions from vendors seeking business with the city. And in return, powerful politicians rewarded his moving company with lucrative hauling and storage contracts. They named him to the Chicago Transit Authority board. With their help, he became a millionaire and a south-side legend–a crude, colorful, self-proclaimed benefactor of the poor.

And then–starting in 1987–Medley did something incredibly stupid: unwittingly or not, he got involved with an operator who was out to bilk the CTA of hundreds of thousands of dollars. Medley called it a legitimate business relationship. But federal prosecutors accused him of taking a bribe, and a jury agreed. It’s autumn 1989 as Medley stands in his vestibule, and he’s a convicted felon facing ten years in prison.

“I’m Medley–I didn’t do any wrong,” he says with passion. “Ask anybody: Medley gives, Medley doesn’t take. Medley’s been giving all his life. Medley didn’t bribe nobody!”

Heading for the door, he encounters a middle-aged black woman who immediately recognizes him. “Don’t worry, Howard,” she says. “The truth will come out.”

Medley smiles back. “The people know,” he says with pride. “I’m Medley. Medley’s not gonna spend no time in jail!”

Medley was 16 when he moved to Chicago from Helena, Arkansas. That was in 1943. He was an orphan. His parents died when he was three. His grandparents raised him.

Tall, restless, and strong–that’s how friends described young Medley. “When Medley puts his mind to something, he gets it done,” says Cook County Board Commissioner John Stroger, a family friend from Arkansas. “He was that way when he was young. He’s a man of boundless energy.”

After a stint in the Navy, he settled on the south side, got married, and had two daughters. The Medleys lived in an apartment; he drove a truck for the post office, making $4,500 a year. But that wasn’t enough–he wanted to make more money; he wanted to own his own building.

So he took a second job, driving a truck at night. “It’s not how much you make but how much you spend that counts,” says Medley. “I told my wife, ‘We’re gonna live on the salary from one job, and save the other.’ But she disagreed. We won’t go into that.”

They were divorced, and he was left with more time to pursue his ambitions.

By 1960 he had saved $9,000. He bought a south-side apartment building, using its rental income to help pay the mortgage. Soon he owned two buildings, and he bought an old, beat- up truck to haul junk from his property. Word spread of his truck. Neighbors asked if he would make light hauls for them. He decided that the time was right to make something of the requests. He papered the south side with fliers announcing a new hauling business. Medley Movers & Storage was born.

His stature grew quickly. Howard Medley was someone who stood ready to be of service.

He loved the power of feeling wanted. He liked it when needy people came to him. He liked it when they told him that no one else could help them as much. “I like to hear them say thank you,” says Medley. “It makes me feel good.”

He saw himself as a man of the people. “Everybody knows Howard,” the Reverend J.C. Austin Jr., minister of Pilgrim Baptist Church at 33rd and Indiana, was saying a while back. “He comes to church almost every Sunday. He likes to sit in the balcony where everyone can see him.”

“I know where I come from,” says Medley. “I won’t ever forget that.”

To hear him tell it, he helped everyone and asked for nothing. “You can’t just be helping the young skinny attractive ones,” Medley says. “Everybody wants to help them. You got to help the old fat ugly ones too.”

According to Medley, he gave money to Little League teams, churches, boys’ clubs, civil rights groups, and even needy-looking strangers he met on the street or in a store. “You couldn’t give Medley nothing,” says the Reverend Willie Barrow, former national executive director of PUSH. “He always said, ‘I don’t need PUSH, PUSH needs me.’ I remember once I couldn’t meet a payroll. I called Howard Medley. I said, ‘I need to have $10,000 to meet the payroll.’ Medley says, ‘You have it.'”

But most important, Medley hooked up with Stroger, Harold Washington, Ralph Metcalfe, and other younger members of Congressman William Dawson’s south-side political organization. It was, in some ways, a peculiar alliance. Many of the politicians were well educated and refined; Washington and Stroger were lawyers. But Medley spoke in a husky growl, his syntax-mangled sentences running on forever. He drove an Excalibur and Cadillacs; he favored gaudy suits and wide-brimmed hats.

Some politicians may have underestimated him, but most admired his drive. His ambition rivaled theirs. He never ran for public office. Instead, he operated in the back rooms–raising funds and twisting arms–handling the nuts and bolts.

“They needed me,” says Medley of the politicians he has known. “I was the guy who could get things done. You want fund-raising tickets sold, come to Medley. Want help downtown–Medley. I was the man. Everybody knows that.”

How much of his talk is truth remains a mystery. A relentless self-promoter, Medley realized long ago that the appearance of power is often as important as the power itself. Sometimes, however, he came on a little too strong.

The first time I talked to him was years ago, maybe 1982. I called to interview him for an article on black politics. He immediately told me that he knew more about black politics than anyone in the city, that he was the most important and influential man (white or black) in city politics, that he was good friends with “Eddie” (Alderman Edward Vrdolyak), that if you wanted a meeting with the mayor (then Byrne) you had to go through “Medley,” and that I was “dumb and naive” for not knowing these things already.

Having said all of that, he arranged a three-way phone conversation, allowing me to listen as some unidentified caller, seeking a city job, asked Medley to arrange a meeting with city officials. To this day, I can’t be sure that the caller wasn’t a plant.

“Who really knows how much power Howard really had?” says a former high-ranking official in the Washington administration. “He’s the kind of guy who would walk into the office of Intergovernmental Affairs and say hi to the secretary. Then he’d go over to the press office and say hello to the receptionists. Then he’d stop by the mayor’s office and wave to the guard. Later on he’d tell you, ‘Today I had to meet with Intergovernmental Affairs, the press office, and the mayor’s office.’ He’s shrewd. If people think you have power, it doesn’t matter if you don’t.”

Whatever its merits, his reputation as a south-side power broker reached Mayor Richard J. Daley sometime in the mid-1960s.

“I called Daley one day to talk about crime in the community,” Medley recalls. “There was a murder on the south side and a murder on the north side at the same time. Only the north side got all the police. So I called Daley–I just called him up. His secretary says, ‘The mayor’s busy.’ I said, ‘I don’t want to have to take this to the papers.’ She said, ‘Just a minute,’ and then Daley picked up the phone.”

For Daley and his machine, Medley was a useful tool. At that time, whole south- and west-side neighborhoods were changing from white to black, as thousands of blacks moved to Chicago from the South. Activists marched for open housing and demanded integrated schools. Martin Luther King Jr. brought his “end-the-slums” campaign to the city’s west side. And Mayor Daley was caught in the cross fire between black demands for equity and white resistance to integration.

Guys like Medley, however, operated outside these larger social struggles. They didn’t press for open housing. What they wanted was the privileges of power–jobs, contracts, and clout–that Daley could provide.

For Medley, it was a tough tightrope to walk. He didn’t want to be obsequious. He never went so far as, say, Congressman Dawson, who called King an outside agitator and demanded that he leave town. On the contrary, Medley raised money and furnished favors for civil rights activists–including the Reverend Jesse Jackson–throughout the 60s and 70s.

What he rarely did was support the independents who challenged Daley’s rule. Instead, he actively raised funds for the city’s black machine aldermen.

For his efforts, the rewards flowed. Medley Movers won county and state contracts to haul or store everything from sludge to election booths. In 1975, Daley asked Medley to take a seat on the Board of Election Commissioners.

“I’ll never forget, [Daley] called me down and told me that he wanted me to become a cabinet member,” says Medley, remembering when Daley asked him to join the election board. “I told him, ‘Mr. Mayor, you’ve been so straightforward with me I think I owe it to you to be honest with you.’ I said, ‘I’m not qualified to be your cabinet member.’ I told him I have such limited education.

“Boy, he didn’t like that. He leaned over his desk and he said, ‘Look, let me tell you, don’t you never say you’re not educated. You take this job and you’ll be one of the most educated people I’ve got down here. You pulled yourself up by your bootstraps.’ I guess he had really looked into my background; he knew everything about me. He said, ‘When people go to school for an education, just think why they are going. Just think of it. They’re going so they can make money, so they can get a chance to live and do the things that you’re able to do out here. You helps this one; you helps that one; you paid your debt to society. All these fellows’–oh, he knew everything about me. He said, ‘Listen, common sense is what your views is.’ He says, ‘Everybody goes to school so they can get an education. They go to get one type of job that won’t pay as much as another one so they gets a degree so they can get that so they can make money.’ He says, ‘So don’t you ever say you’re not educated.’ Oh boy, when I walked out of Daley’s office I must have felt I was ten foot tall.”

With that job came the title commissioner, as well as an avalanche of criticism. The commission is a three-person board (two Democrats, one Republican) that oversees local elections. Its members are not supposed to participate in partisan politics. They’re not supposed to do business with governmental entities. And yet, within a year of his appointment, the newspapers were reporting that Medley had paid for a Democratic candidate’s fund-raiser, and that his moving company still received city contracts.

A coalition of reformers sued to have Medley ousted from the board. By then Daley had died and Michael Bilandic was mayor. To avoid a court showdown, Bilandic asked Medley to leave the election board and take a seat on the CTA.

In some ways, the transfer was an advancement. The CTA is a multimillion-dollar agency, overseeing thousands of jobs. Back then, Medley was its only black board member. Medley became the go-to guy for black politicians seeking CTA patronage or businessmen seeking CTA contracts.

“I was the lowest bidder for five years and each time the CTA refused to give me a contract because they said I was not qualified,” says Robert Digby, president of Digby’s Armored Express, a security service that gathers change from el stops. “Then Medley stepped in, and ever since the CTA has given me the contract. I said, ‘Howard, if there’s anything I can do to help you, let me know.’ He said, ‘Shut up. If you talk like that, I won’t help you anymore.'”

Medley relished his role. “He thought of himself as the people’s board member,” says a longtime CTA employee. “His big deal was getting kids jobs on the summer work program. You should have seen those kids –they’d come in here all the time with their resumes, asking for ‘Commissioner Medley.'”

Apparently, his generosity had a price. In 1984, for instance, Nikki Zollar came to Medley on behalf of her law firm, Kirkland & Ellis. Zollar was a young black attorney. Medley was an old family friend who might help her make a good impression by bringing her employers some lucrative CTA legal work.

“Medley told me he had often helped young people get business, that he had helped a young man at O’Hare get [some] taxi business, and that young man gave $25,000 to be used for the community,” Zollar would later testify at Medley’s sentencing hearing. “I said I did not have $25,000. . . . He said [Kirkland] could contribute.”

The federal prosecutors described this incident as a shakedown that failed. For as they made clear, Kirkland did not give Medley any money and the CTA did not give them any law business. “Medley operated without restraint or punishment for too long,” said U.S. assistant attorney Jeffrey Stone, chief prosecutor in the Medley case at the time of Medley’s sentencing. “He’s cut so many deals he has lost his ability to distinguish between right and wrong.”

Medley, of course, saw it differently. From his perspective, he was, as they say, just doing a little quid pro quo. He never intended to pocket Kirkland’s money, he says now. Instead, he planned to distribute it to needy groups and churches in the community. Without pressure from the inside, he argued, corporate Chicago would never help inner-city blacks.

As he saw it, all power brokers–black and white–make deals. That’s how they get things done. “Mayor Daley used to say, ‘If you want things done, give it to Howard and get out of the way,'” says Medley. “That’s what it’s about–getting things done.”

Beyond the deal making, his position on the CTA board gave Medley a stage. He was a ham who didn’t hesitate to lead reporters on “waste-exposing” raids into bus garages and el stations. He called himself the “hardest-working member on the CTA board,” and many observers agreed.

“I’ve been with him on the tracks, walking over third rails, to see who was defacing our property with graffiti,” says John Hoellen, a fellow board member. “His effort for the board was exhausting.”

Behind the scenes, he waged a series of power struggles with other board members and top CTA employees. “He liked to remind us that he was the boss,” says a former senior CTA official. “He’d say, ‘Don’t forget: you have to report to me.'”

For a while, his chief adversary was former CTA chairman Mike Cardilli. In 1982, Cardilli sought to have his chairmanship extended, and Medley voted against him. After that vote, Medley says he got a call from the late Charlie Swibel–a political operator with close ties to Mayor Byrne. “Wrong vote, no business,” Medley said Swibel told him. Outraged, Medley publicly accused Swibel of threatening to kill his contracts with the city.

As word of the confrontation spread, Medley and Swibel conferred in a closed-door meeting convened by Edward Vrdolyak. After that, peace reigned: Cardilli got his extension and Medley kept his contracts.

“Today I talked to Mr. Swibel and I must say in all honesty that any alleged threat or any suggestion that Mr. Swibel threatened me is untrue. . .” Medley said in a prepared statement that contradicted his comments before the private meeting. “Most friends have differences from time to time. Mr. Swibel is my friend and my concern today is that our friendship continues.”

“I didn’t even know that he [Medley] had trucks that were being hired by the city,” said Swibel, presumably with a straight face. “Medley is a friend of mine. I would never threaten him. You know me better than that.”

These theatrics earned Medley the enmity of reformers and editorial writers. They called him a phony who cleared all of his actions with whoever happened to be mayor. For instance, in 1981 he took a television crew on a tour of a CTA cash-counting facility. They discovered hundreds of dollars scattered on the floor, and Medley went on TV to blast the CTA for sloppy procedures. Black activists, however, immediately accused Medley of having staged the raid to give Mayor Byrne an excuse to fire Eugene Barnes, the CTA’s first black chairman.

Medley “is as naked and unashamedly an Uncle Tom as any of the white-catering Harlem hustlers who would peddle the flesh of their own sisters to satisfy the lascivious desires of white thrill seekers . . .” raged “the Axeman,” a columnist in the Chicago Metro News, a south-side newspaper. “Mayor Byrne used Medley against Barnes . . . to soften the political repercussion in the black community.”

Medley says such criticism never bothered him. But he worried that some board members might dismiss him as a bumpkin. He was a little insecure about his lack of formal education. He held lawyers and other professionals in high esteem. He often bragged about how they answered his phone calls and came to him for favors.

“His problem,” says Hoellen, “is that he has to be a big shot.”

Some reformers predicted Medley’s downfall with the 1983 election of Harold Washington. After all, they said, Washington was a “movement mayor,” and Medley a hack.

The reformers were wrong. Medley made his services available to Washington from the outset. He raised money for Washington’s campaigns, and bragged that he and the mayor were as close as “a couple of brothers.”

“His devotion to Washington was almost idolatry,” says Hoellen. “He became an ideologue. To him, Washington could do no wrong. That attitude bothered me.”

As always, it wasn’t clear how much influence Medley truly wielded. “Howard liked to call Harold, and he liked it that Harold took his calls,” says the same former Washington official who’d told me Medley could say hi to a secretary and describe it later as an important meeting. ‘He’d call Harold at six in the morning and say something like, “If you’re going downtown today, I’d like to ride with you.’ And Harold would let him ride downtown. And everyone would see Medley get out of the car with Washington and think, ‘My God, Medley has power.’ Harold was like that with a lot of people. There are guys all over this city who are convinced that they were Harold Washington’s number-one man.”

Medley’s maneuvering had a purpose. He wanted Washington to have him made chairman of the CTA board. Mayoral aides say Washington would never have done that. But Medley never gave up hope.

These were heady times; Medley had come a long way since Arkansas. And what was wrong with that?

If anyone knows, no one at the CTA will say how it was that the board–then chaired by a black Washington appointee, Walter Clark–awarded a two-year, $38 million diesel-fuel contract to Brian Flisk, a reputed white slumlord, under the guise of affirmative action.

Originally, that prize had been Mobil Oil’s. But in September 1986, the CTA board voted to reject Mobil and award the contract to Flisk and his company, Metropolitan Petroleum, on the grounds that Mobil did not have a legitimate minority subcontractor (an allegation Mobil denies).

Flisk, 43, did have a minority subcontractor (a company called Casey Fuels). But Flisk’s company, Metropolitan, was virtually unknown; Flisk had bought a controlling interest in it in 1982.

In 1973 the Tribune had named Flisk one of the city’s ten worst slumlords. More recently, the paper recalled Flisk as a “flamboyant” operator “working out of a telephone-equipped limousine and residing in a penthouse on South Lake Shore Drive” who had managed or owned more than 400 buildings and “had been sued repeatedly for building-code violations.”

Flisk now promised to charge the CTA 11 cents a gallon for diesel fuel–20 percent less than the going rate–provided the authority paid within 15 days of receiving his invoices. The arrangement hinged on support from a company called Heller Financial Services, which had established a $5 million line of credit for Flisk. Flisk would borrow from Heller to buy fuel from distributors and resell it to the CTA, whose receipts would enable him to repay Heller. At the time the contract was awarded, it could not have been clear how Flisk stood to make any money from the deal, since he was, in effect, promising to sell the fuel for less money than it cost him.

When the contract was awarded to Metropolitan, Medley didn’t know Flisk, both men say. Medley knew Flisk’s business associate, Howard Weitzman, another white property owner. But Medley apparently didn’t meet Flisk until January 1987.

That meeting–arranged at Flisk’s request by a former Third Ward precinct captain named Lindsley “Jelly” Holt–occurred in Medley’s CTA office. The CTA was then conducting an internal inquiry into allegations that Metropolitan’s diesel fuel was tainted and its arrangement with Casey Fuels bogus.

Flisk would later testify that at their first encounter he complained to Medley that the inquiry was a “witch-hunt” set up by CTA insiders “promoting Mobil Oil.” Medley promised to look into the matter–and threatened to have Flisk’s contract yanked if his story didn’t hold up, Flisk said.

A few weeks later they met again–this time over breakfast at the Hyde Park Hilton. The conversation turned to fund-raisers. Afterward, Flisk accompanied Medley to his apartment to buy tickets to some events sponsored by the Washington-for-mayor campaign. It was there, according to both men, that Flisk told Medley he planned to move his company to a larger building, and asked if Medley knew of any property for sale.

As a matter of fact, replied Medley, he had just heard about a large warehouse for sale at 4800 S. Central. It was owned by a consortium that included three prominent lawyers: Robert Sperling, Donald Kahan, and Michael Zavis. Sperling was Medley’s main connection. He worked for Katten Muchin & Zavis, a large and well-connected downtown firm. They’d met years ago, when Sperling had been a staff lawyer for the Chicago Board of Election Commissioners. After that, when Sperling was in private practice, he had come to Medley on behalf of several currency exchange owners, Medley says, and Medley had introduced him to Harold Washington, then a state legislator proposing currency exchange reforms.

In time, a mutually benefiting relationship developed between the two, Medley says. According to Medley, Sperling occasionally invited him to lunch in the law firm’s private dining room. They talked politics, and sometimes Sperling contributed to the NAACP or to other Medley causes. In 1987, Sperling asked Medley to arrange another meeting with Washington, Medley says. Sperling, Medley continues, wanted to make sure that Katten maintained its share of city bond business. Medley says he arranged the meeting and that Katten’s contracts were preserved.

When Brian Flisk asked him about property for sale, says Medley, he called Sperling and told him about Flisk. After several months of bargaining, Flisk agreed to lease Sperling’s building with an option to buy. “Sperling said, ‘If they buy that building, you’re going to get a commission,'” says Medley. “I said, ‘Sperling, you don’t owe me a thing. I was glad to help.’ But he insisted.”

Medley agreed to accept $300,000–or 6 percent of the warehouse’s $6.8 million purchase price–to be paid in regular installments of $25,000. There was one hitch. Medley was ineligible to receive a finder’s fee because he was not a licensed broker. So Medley asked John Wilson, a broker, to funnel the fee to him.

In the meantime, Medley started looking into Flisk’s complaints about the CTA “witch-hunt.” He talked to the CTA’s affirmative-action officer, as well as to its directors of investigations and maintenance. At Flisk’s request, he drove to a 69th Street garage and watched fuel being unloaded and tested. Over time, Medley says, he was convinced that CTA employees were improperly testing the fuel and that Metropolitan’s arrangement with Casey Fuels was legitimate.

“Flisk met me at the garage and we saw that they [CTA employees] were testing the fuel after it had been loaded into the tanks,” says Medley. “They should test it when it’s in the truck. There’s water in those tanks that dilutes the fuel.”

Nevertheless, CTA auditors recommended that Flisk’s contract be suspended, and on March 4, 1987, the board assigned the matter to a subcommittee chaired by Natalia Delgado. After that board meeting, according to Delgado’s trial testimony, Medley privately talked to Delgado in the hallway of CTA headquarters. Then he called her at her law office. A few days later he called her again. Each time he expressed concern that Metropolitan had been wronged. At no time did he tell Delgado about his part in the pending real-estate deal between Sperling and Flisk.

By the end of March, the board had decided that the allegations against Metropolitan could not be substantiated–the company kept its fuel-delivery contract. On April 14, Wilson was written a $25,000 check–not by Sperling, curiously, but by Flisk’s associate Howard Weitzman. Afterward, Wilson gave Medley $22,500. “Wilson got to keep [$2,500] for his troubles,” Medley says.

The issue faded from view, but it was far from dead. CTA officials were concerned about the time it was taking the CTA’s billing office to pay Metropolitan for fuel. Often, more than two weeks elapsed from the time the CTA received Metropolitan’s invoices to the time it mailed Metropolitan its checks. As a result, the CTA was “overpaying” Metropolitan, or at least not receiving its 20 percent prompt-payment discount. Something seemed fishy, so CTA officials Gloria Chevere and Robert Paaswell froze about $400,000 in payments for already-delivered fuel until the matter could be resolved.

Without that money, Flisk couldn’t pay his suppliers to deliver fuel, nor could he repay Heller Financial Services. He pleaded for the $400,000, but Chevere and Paaswell stood firm. In July 1987, they canceled Flisk’s contract. Soon after, Metropolitan went out of business and Mobil started delivering fuel to the CTA.

By this time, Heller–demanding its money from either Flisk or the CTA–had called the U.S. attorney’s office. They began putting a case together. Eventually eight persons were indicted, foremost among them Medley and Flisk. Flisk was accused not only of bribing Medley to smooth over his troubles with CTA investigators, but also of bribing a couple of functionaries in the authority’s accounts payable department. These clerks, according to the indictments, accepted back-dated invoices from Flisk’s company, thus forcing the CTA to pay some $624,000 in “late payment” charges.

Ronald Buzil, who’d been Metropolitan’s controller, was charged with filing false information with the IRS. He agreed to secretly tape-record Flisk, who was not only his old boss but also his brother-in-law. In December 1987, they met.

For a while, Buzil and Flisk exchanged small talk about the recent death of Mayor Washington. “They had him laying in state for two days in City Hall,” Buzil said.

“Yeah?” Flisk replied. “He could lay out there for a week and wouldn’t stink?”

“Did you go down there?” Buzil asked Flisk.

“Fuck no,” said Flisk. “I wouldn’t be one of those people.”

Eventually, they got around to the subject of Medley. “He [Medley] made a lot of money off the whole thing,” Buzil said. “He was greedy.”

“What are they [the federal prosecutors] gonna give me if I give him [Medley] up?” Flisk asked.

Buzil never answered that question. And during the conversation, Flisk did not admit he had bribed Medley. But prosecutors were convinced that Medley–in exchange for $25,000–had stymied the CTA’s internal inquiry into Metropolitan. They subpoenaed Medley’s phone records and discovered that within a few weeks of their first meeting, Medley had made about a dozen calls to Flisk. What were they talking about, if not their real-estate deal or the inquiry? And why had Medley so diligently pressed Flisk’s case to Delgado?

The prosecutors were convinced that the ardor with which Medley had intervened on Flisk’s behalf–particularly at the 69th Street garage–belied any pose of neutrality. The foreman and pump jockey at the 69th Street garage would later testify that Medley had insisted they accept the fuel, even though they told him it was diluted. “Their method of testing was not improper, as Medley claims, and they told Medley that at the time in the garage,” said Stone at the trial. “But instead of backing up the CTA employees, Medley backed up Flisk.”

The so-called real-estate deal was a ruse, prosecutors contended, to line Medley’s pockets. “The motive was money,” Stone would say in his closing argument. “Medley received $25,000 and was promised a good deal more.”

News of his indictment reached Medley as he was preparing for an April 6, 1988, CTA board meeting. With many of his enemies in the authority watching, Medley stood before the cameras and proclaimed his innocence. He claimed to be the victim of a series of unusual coincidences. He said he hadn’t known that the check to Wilson was signed by Weitzman. He said he had assumed that Sperling provided it.

As Medley saw it, he and Flisk had made a personal deal. It was only a coincidence that he, Medley, was a CTA board member and Flisk a CTA vendor. Medley believed his finder’s fee was legitimate.

As for the phone calls and the garage visit, what was unusual about that? Over the years, Medley claimed to have spent countless hours investigating countless complaints. That was his style: relentless, persevering. You didn’t have to be a well-connected CTA vendor to get Medley’s ear. His door was open to anyone. He was the people’s board member–remember that?

His first trial began in November ’88. “Howard Medley was one of the most politically powerful men in the city of Chicago,” prosecutor Stone told the jury. “He sold his office and he sold his integrity for a secret bribe of $25,000.”

Medley’s lawyer, James Montgomery (he’d been Chicago’s corporation counsel under Washington) dismissed Stone’s allegations. This case, said Montgomery, boils down to a legitimate real-estate deal between Flisk, Medley, and Sperling and the other lawyers. Sperling and his associates leased out their building; Medley got paid for his introductions, and Flisk fattened Harold Washington’s reelection chest.

“In the business of politics, it is a business of favors for favors,” Montgomery said. “And that’s not against the law.”

Montgomery brought on Sperling to testify that he’d told Medley he could not pay him a finder’s fee and had suggested alternatives: one was to give the fee to a charity Medley favored; another was to give the fee to a licensed broker. And that is what happened–even if the check to John Wilson was written by Weitzman instead of Sperling (something Medley has maintained he didn’t know).

The prosecution insisted that it actually made no difference who wrote the check. As Medley must have known, Flisk was the source of the money Medley got because it was Flisk who was paying Sperling and the other two lawyers for the building. Yet the prosecutors wound up asking the jury to interpret this complicated deal as a bribe without producing a single witness to say that bribing Medley was Flisk’s intention. The jurors didn’t buy it. Eleven of them voted to acquit Medley, while the twelfth held out for conviction.

A mistrial was declared, and prosecutors decided to try Medley again. “At the end of the first trial the jurors told us that they were ‘waiting for the other shoe to drop,'” says Stone. “They wanted to hear from Flisk.”

For the second trial, Stone would have to produce Flisk. In the meantime, Flisk had pleaded guilty to several counts of racketeering and been sentenced to four years in jail and fined $450,000. Montgomery’s obvious strategy was to portray Flisk as the mastermind who duped Medley. But Medley rejected that approach. He didn’t want to admit that any wrong had been done, and he certainly didn’t want to present himself as Flisk’s unwitting fool.

Besides, the near-acquittal had bolstered his confidence. The black community had rallied around him–even the militants who had once called him an Uncle Tom. The way a lot of folks saw it, the prosecutors hadn’t come close to proving that either Flisk or Medley thought of their transaction as a bribe. There was no eyewitness testimony or tape recording that had Flisk telling Medley, “If you fix this CTA inquiry, I’ll get you $25,000.” They had an appearance of impropriety, and that was not enough to send a man to jail. One white guy had leased a building to another white guy, so why punish Medley? If Medley had done wrong it was in trusting Flisk and trying too hard to please Sperling.

“Howard has always been too impressed by rich and powerful white people,” says a friend. “This time they did him in.”

Medley helped form a committee–the Legal Fairness and Justice Fund–to raise money for the defense of other indicted black leaders. Over 500 people attended their first fund-raiser–a $50-a-plate testimonial dinner honoring Medley. Jesse Jackson gave a speech, and speaker after speaker lauded Medley.

Medley’s supporters hailed him as a martyr–one more black leader hounded by the feds. They likened his plight to that of other black politicians–like former alderman Clifford Kelley–who’d been set up by white operators with criminal pasts. (Kelley pleaded guilty to taking bribes from Michael Raymond, an FBI operative who supposedly was acting on behalf of a company seeking city business.)

“Who are all these whites who operate in the black community?” asks Darrell Parrish, a publicist and longtime friend of Medley’s. “How come they move around so freely? Who’s giving them their protection?”

To Medley’s supporters, it didn’t matter that dozens of white politicians here had been sent to jail over the years. Or that Medley had displayed inexcusably bad judgment in even introducing Flisk to Sperling. The wounds were fresh. Mayor Washington was dead. A new Daley was mayor. And now here was one more black leader–no matter how tarnished or controversial–facing time in jail. “They didn’t throw Howard into jail,” notes Parrish, “when he was doing deals for Byrne and Bilandic.”

As time between his trials wore on, Medley went on the offensive. He hired Rae Jones, a free-lance writer, to write his life story. Jones produced a half dozen pages that tell of his rise from rags to riches and are sprinkled with aphorisms preached by Medley’s grandfather George Medley, an Arkansas farmer.

“If you get money, except one way–the honest, hard-working way–it’s not yours,” says Medley’s saga. “God said live off the sweat of your own eyebrow. That’s what my grandfather said. That’s what he did. And that’s what I did.”

He started reaching out to the press. When his publicist friend passed on word that I was interested in writing an article, he called. After that he sent me a copy of Jones’s biography. A few days later, he sent a tape he had made–filled with vintage Medleyisms–in which he repeated the story of his impoverished youth and offered pieces of philosophy.

“I help anybody who comes to see me,” Medley says on the tape. “I never forget, a lady came in. She was in her early 40s. She was real heavy, not too attractive. You know those people don’t get help. The little cute ones–everybody runs to help them. So I take people like her. I help her quicker than I’d help another one. So I talked to her. She told me about the problem she was having. She was trying to get her daughter a [CTA job] application. Well, they were hiring down there. So she brought her daughter in and I could see why [no one helped her] because her daughter looked just like her–five-by-five. Anyway, I told them to give her daughter an application. So she didn’t pass [her job test]. So then she came back to me, she wanted to see me private. She wanted to talk to me. I told her, ‘Look, don’t disrespect me. Don’t ask me to do something unethical. I’ll help you, yes.’ I said, ‘My daughter got a job down here, but she passed the exam.’ I said, ‘No, don’t do that. Don’t ever ask people to do things like that. Try to do things honest.’ I said, ‘Do you realize if I go tell a person to tell a person to go do that I’m not their boss no more? They got me now. If I tell them to do something crooked, they have me. Don’t ask me.’ But she apologized later.”

Soon after we had our lunch. It was a sunny day, and as we walked to a fish restaurant near his apartment, several passersby–including two off-duty bus drivers–stopped to shake Medley’s hand and wish him luck.

In the restaurant he was immediately greeted by the cashier and the waitress. He sat by the salad bar and in a rambling 30-minute discourse–during which he managed to avoid answering any questions about the case–boasted of his charity, while pulling from his coat a little black book with the phone numbers–home, work, and car–of many big shots, including Jackson, Vrdolyak, Daley, and Byrne.

Then he called another customer–a woman–to his table.

“Let’s say you needed something done in City Hall,” he said softly, in a folksy voice. “Who are you going to go to?”

She was silent.

“Would you go to the alderman?” Medley asked.

“No,” she said.

“Would you go to the committeeman?”


“Well, then who?”

She looked puzzled. Finally, she spoke: “You?”

Medley beamed. Later, on the way out, he asked the counterman the same question.

After some thought, the counterman answered: “Alderman [Tim] Evans?”

Outside the restaurant, Medley still looked disappointed. He didn’t even brighten when a bus pulled past and the driver honked the horn and waved.

In time, Medley got angry at Montgomery for not letting him take the stand. “I shouldn’t have listened to my lawyers,” Medley said after the first trial. “He didn’t let me tell my side of the story.”

So Medley fired Montgomery and refused to pay his fee. (Last October, Montgomery sued Medley, seeking to recover over $200,000 in fees and expenses.)

In retrospect, most observers–as well as Medley himself–agree that firing Montgomery was a mistake. “I don’t blame Montgomery for not putting Medley on the stand,” says one observer of the case. “Medley’s too unpredictable. I don’t think he’d have made a sympathetic witness.” (Medley did not testify in his second trial either.)

With little time to prepare, Medley’s new lawyer, Stanley Hill, mounted a defense that lacked Montgomery’s preparation. Flisk made a reluctant but damaging witness. Cross-examined by Hill, Flisk insisted that the $25,000 payment to Medley was not a bribe. But then Stone made Flisk read out loud that portion of his plea agreement in which he admitted to having “tendered a bribe to [Medley] . . . to help deflect internal and public criticism of the manner in which [Metropolitan] was performing its diesel fuel contract with the CTA.”

It took the jury only three hours of deliberation to reach a guilty verdict. “They [the jurors] may figure it’s justice, but I don’t,” Medley later told reporters. “I’m Medley. I’ll win this thing on appeal.”

The December 15 sentencing hearing in U.S. District Judge Charles Kocoras’s court lasted more than three hours. After a parade of character witnesses–including John Hoellen, John Stroger, Willie Barrow, and banker Jacoby Dickens–Medley spoke. He asked to be sworn in, which was unnecessary, since at this point nothing he said could be held against him.

Mostly, he read from a prepared text that reiterated his defense: he didn’t know the check came from Weitzman, that sort of thing. “I don’t know what’s going to happen here today,” he said. “But so help me God, no one ever bribed Medley.”

He allowed that the facts might persuade the prosecutors that something wrong was done. But he acknowledged no guilt and he showed no remorse. He talked for about 30 minutes. He quoted his grandfather. He started to ramble. As he left the stand, he walked up to the chief prosecutor, reached out his hand, and said: “Mr. Stone.” “Mr. Medley,” Stone quietly replied, and turned away without taking Medley’s hand. His head high, Medley returned to his seat.

Finally it was time for Kocoras to announce his sentence. The judge, who had presided over both trials, sounded a little weary. “I don’t doubt for a minute that you have done a lot for your community,” Kocoras said, looking straight at Medley. “But when [Flisk] got into trouble he came running to you, and you took his bidding.”

Medley started to interrupt, then kept quiet. “The money wound up in your pocket,” Kocoras continued. “Those are the facts I deal with, and they are not kind to you.”

With that, Kocoras fined Medley $10,000 and sentenced him to 30 months in prison.

Hill asked the judge to extend bond, allowing Medley to remain free until his appeals were exhausted. A month later Kocoras denied that request, and Medley entered the federal penitentiary in Duluth, Minnesota. But such was the impact of the sentence on the courtroom, its weight was felt the moment it was pronounced. Medley’s daughters wept; friends offered their condolences.

Downstairs in the lobby, a bunch of reporters and cameramen awaited his comment. But this time Medley walked past the reporters. With his daughters by his side he went home–to his community. For the first time most of the reporters could remember, Howard Medley had nothing left to say.

Art accompanying story in printed newspaper (not available in this archive): photo/Garland Hale.