In the past four months, City Commissioner Randy Leonard has remade himself.

Leonard has whittled his physique down to muscle and bone. By running and hitting the weight room at 24-Hour Fitness near City Hall, he's dropped 35 pounds.

"I used to bench 225 in my heyday, and now I work out with 135," Leonard says. "I do a lot of reps, do 60-pound military press, do 25-pound dumbbell and then dips."

Today, Leonard's jeans fit loosely. His half-moon face, shorn of the fireman's mustache he wore for years, is gaunt.

Leonard says there is no specific reason for his new health kick.

"I just wanted to feel better," he says.

But the makeover comes at a time of great stress.

Professionally, Leonard, 57, is the most dominant elected official in Portland.

He runs the Fire and Water bureaus and the Bureau of Development Services, which puts him in charge of many core city functions.

More than that, he is the City Council's go-to guy, filling the vacuum created when a sex scandal engulfed Mayor Sam Adams last January.

"Leonard sets the agenda," says Pacific University political science professor Jim Moore. "You'd have to go back decades to find examples of somebody who's exercising power the way he is now."

Former Mayor Vera Katz, now a City Hall lobbyist, agrees.

"Randy plays a major role in nearly every issue, and many times views himself as the mayor," Katz says.

But Leonard is also dealing with challenges that would unravel most pols.

His personal life is in shambles. He recently faced a criminal investigation from the Multnomah County District Attorney's Office. And although he has long deflected allegations of cronyism and self-dealing, critics say power is turning him into a not-so-benevolent dictator.

"Leonard has tremendous power, and he uses it in ways that are arbitrary and capricious," says Chris O'Connor, a public defender who has clashed with Leonard over the tactics a Leonard-led team used to target repeat offenders.

Leonard says the notion he has great power is "a myth."

In the evenings these days, instead of heading home, he often hits the gym and runs alone along the Willamette in the dark, crossing the Steel Bridge to the Eastbank Esplanade, and back across the Hawthorne Bridge. The run offers a magnificent view of the city he increasingly controls, and temporary refuge from those challenges he cannot.

"I find it very peaceful," Leonard says.

Randy Leonard is a man of action. But toward the end of the summer, he found himself paralyzed.

"I had a lot of vacation to use up, and I couldn't go away and I couldn't work," Leonard says. "All I could do is sit there."

That's because Leonard's family life has come to echo a sad country-western song.

For much of the past year, his oldest child, Kara Leonard, 30, was wanted on criminal charges in both Oregon and Washington.

Kara's crimes were relatively minor. In 2006, police arrested her for trying to obtain Vicodin with a forged prescription at two Clark County pharmacies.

She subsequently missed a series of court dates, leading to a warrant being issued for her arrest. In Portland, she was arrested for shoplifting at Macy's last year and again failed to show up for court.

Until now, Leonard has not talked to the press about his daughter's legal troubles.

"The sooner she got taken into custody, the better," Leonard says. "The one thing I wouldn't do is ask the Police Bureau to arrest her, and I could have, because her mom and I both knew that the best place for her to be with her addictions and her associations is in jail."

In a letter she wrote last year to a Clark County judge, Kara Leonard explained that she'd "been an addict for 12 years" and was then in a residential treatment program, which was the only thing keeping her alive.

She'd previously left treatment for a court date and used drugs, she wrote.

Leonard's daughter's travails are not the only family issue weighing on his mind.

His second marriage broke up a couple of months ago. He says he and his wife, Julie, whom he met when he was a firefighter and she worked in the city office dealing with police and firefighter pensions, are preparing to file for divorce after 12 years.

"I work too much and stay up too late doing my work," Leonard says. "That's what cost me my marriage."

While Julie Leonard remained in the couple's 3,900-square-foot Mount Scott home, Leonard spent the past couple of months living above his chief of staff's garage in Southeast Portland.

And last week, Leonard had to give his beloved 11-year-old German shepherd-boxer cross, Rosey, to his first wife because, being newly single and gone all day and many evenings, he could no longer take care of her.

"I wouldn't wish what I've been going through on my worst enemy," says Leonard. "I've been humbled."

As a politician, Leonard has a lot to be proud of. He is energetic, decisive and far more candid than most elected officials.

In a City Hall where property developers usually get what they want, he has rejected tax abatements for condo towers and pushed back—hard—when the business lobby complained about taxes.

He's passed a ballot measure that reined in the city-owned Portland Development Commission, shaken up stodgy bureaus and even delivered some pork to his beloved alma mater, Portland State University, by persuading colleagues to move the city archives from North Portland into the lower level of a brand new PSU student center.

But amid such accomplishments, there have also been warning signals from Leonard's past. In 2005, after he'd twice been elected to council, The Oregonian unearthed records revealing alcohol abuse and allegations of domestic violence from Leonard's first marriage, which ended in the mid-'80s.

(Leonard denies ever hitting his wife or any other woman, and no longer drinks.)

More recently, WW has learned of an accusation that he steered business to his brother when Leonard worked for the Fire Bureau.

Leonard retired from the Fire Bureau in 2002 to run for a council seat vacated by Commissioner Charlie Hales.

The Fire Bureau is one of the city's most cohesive tribes—thanks in no small part to Leonard's leadership of the Portland Firefighters Association Local 43, from 1986 to 1998. It was at the union that he honed his political skills, working doggedly to improve firefighters' compensation.

And while the police may generate more headlines, it is Portland's 755 firefighters whose endorsement and manpower politicians most covet at election time.

"The public's perception is that firefighters are heroes," says political consultant Liz Kaufman.

"When Randy ran the union, they'd not only make lawn signs [for candidates the union supported], they'd put them up for you," adds Kaufman, who worked on Leonard's 2002 campaign.

Mementos from his firefighting days fill Leonard's City Hall office. Most prominent is a ceremonial ax hanging on his wall, dedicated to "Brother Leonard."

But in July of this year, Chuck Hegele, who owns American Sprinklers Inc. in Portland, lodged a complaint about Leonard's tenure in the Fire Bureau.

Although Hegele's allegations concern the period between 1982 and 1985, the Multnomah County District Attorney's Office took them seriously enough to assign its chief criminal investigator to the case.

Leonard joined the Fire Bureau in 1978. In 1982, he transferred to the Fire Marshal's Office, which is responsible for ensuring buildings have appropriate safety features, such as sprinkler systems.

Leonard worked in the Fire Marshal's Office until 1985, and then left to become fire union president.

Hegele told investigators that while Leonard worked in the Fire Marshal's Office, Hegele noticed one of his competitors getting a disproportionate share of Portland's sprinkler business. That competitor? Leonard's older brother, Rick.

Although Rick Leonard had worked for a sprinkler company prior to 1982, he conceded to an investigator that he created his own company "in '81-'82" and abandoned it three years later, mirroring the period of time his brother was a fire marshal.

In a July 2009 interview, Hegele told the D.A.'s investigator that he confronted Rick Leonard during those days.

"And he was bragging about how his brother [Randy] was pumping him work through the fire department," Hegele said, describing a scheme in which fire marshal staff would hand out Rick Leonard's business card after issuing citations.

In August of this year, the D.A.'s investigator interviewed Leonard and his brother, both of whom adamantly denied any wrongdoing.

On Aug. 27, the D.A's office closed the case, having found "no evidence of criminal or unethical conduct," according to a summary written by Deputy D.A. Don Rees.

Investigators did not interview anybody other than Hegele and the Leonards. Nor did they explore any correlation between citations written when Randy Leonard served in the Fire Marshal's Office and the sprinkler permits Rick Leonard received during that time.

The investigation into Hegele's claims seemed cursory, although as Rees pointed out in his report, the allegations concerned activity from more than 25 years ago, well beyond the statute of limitations for official misconduct.

Randy Leonard says the investigation was a total waste of time. He adds he was unaware his tenure in the Fire Marshal's Office coincided with the years his brother ran his own sprinkler company.

"I wouldn't have known that if you had not told me," he told WW.

The investigation included one other noteworthy aspect. Fire Marshal John Nohr and investigator Greg Wong interviewed Hegele on July 2. They taped the interview and gave a transcript to the D.A.'s office. But first, they gave Leonard a copy before he was interviewed.

That's unusual.

"It is generally inadvisable to provide witness statements to the subject of a criminal investigation prior to the case being reviewed by law enforcement," Deputy D.A. Rees noted in his final report.

Though investigators found no evidence Randy Leonard did anything wrong, the commissioner has certainly used public resources to take care of his own over the years.

An unusual number of people with personal connections to Leonard are, or were, on the city payroll.

One of the first people to join his staff when he took office in 2002 was Stacy Chamberlain, daughter of Oregon AFL-CIO boss Tom Chamberlain, Leonard's close friend and successor as fire union president.

The next year, Leonard hired Jimmy Brown, whom he'd known since kindergarten, to head the Office of Neighborhood Involvement.

Tom Chamberlain's son Joe was until recently a code compliance officer in Leonard's Bureau of Development Services. Leonard's own son Ryan works as a 911 operator in the Bureau of Emergency Communications.

There were others as well—so many, in fact, that then-Auditor Gary Blackmer produced a report in 2007 critical of city hiring practices that was a thinly veiled shot at Leonard.

The audit described loopholes bureaus use to skirt civil service and competitive hiring practices—which are designed to "separate the recruitment and advancement of employees from political patronage and favoritism." Two of the top three offenders were bureaus of Leonard's.

Leonard notes that while job candidates may have connections to him, he rarely makes hires himself.

He also argues their connections to him might even have hurt their prospects. He calls questions about whether such hires constitute cronyism "disingenuous."

"I grew up here," Leonard says. "The folks who are associated with me are the most personal reflection of me possible. Would I actually place my future in the hands of somebody whose only qualification is being my friend?"

Leonard's political decisions also often turn on personal relationships.

In 2006, for instance, Trail Blazers owner Paul Allen, who put a quarter-billion dollars of his own money into the Rose Garden, asked City Hall for financial assistance.

Leonard, who had no ties to Allen, panned the request.

But last year, when Portland Beavers and Timbers owner Merritt Paulson, whose investment in Portland is far smaller than Allen's, sought to bring Major League Soccer to Portland, Leonard championed a far greater city subsidy for Paulson than the one Allen requested earlier.

The difference is Leonard's friendship with lobbyist Greg Peden, who represents Paulson.

Leonard says he got to know Peden in Salem in the '90s, when Peden worked for then-Gov. John Kitzhaber and Leonard served in the Legislature. Peden later became the City Hall lobbyist for the Portland Business Alliance.

Without Leonard's loyalty to Peden, it is unclear whether MLS would ever have gained traction in City Hall.

"Greg has always been and remains a very straightforward and honest guy," Leonard says. "It was very helpful for Merritt's cause that he first had Greg meet with me so that I could ask questions knowing I was going to get straight answers."

As an east Portland lawmaker in Salem from 1993 until 2002, Leonard worked hard for organized labor and also displayed a skill at working the public treasury for his benefit.

In 1997, he amended a bill to allow members of the Portland Fire and Police Disability and Retirement system who served in the Legislature to earn pension credit from the city system rather than the state Public Employee Retirement System while serving as lawmakers. The difference was substantial, because public safety officers get paid far more than lawmakers and remaining in the city pension system would allow them to retire earlier.

A June 1997 memo from City of Portland lobbyist Jackie Bloom shows Leonard did not consult city officials about the change and noted the city's "opposing the amendment on both fiscal and policy grounds." The memo added that the amendment was worth "at least $100,000 and closer to $200,000" to Leonard personally.

Leonard's amendment benefited just two people—him and then-Portland police detective and state Sen. John Minnis—and would not benefit any future lawmakers in the same position.

"I thought then and still think it was a fair approach," Leonard says.

Leonard also takes full advantage of Oregon's lax campaign finance laws. As a city commissioner, Leonard is well-compensated, earning a salary of $96,000 in addition to his fire pension of about $50,000. When he finally retires from City Hall, he'll be allowed to draw another pension from PERS.

Despite his overall compensation in the mid-six figures and a city expense allowance, Leonard has, so far in 2009, spent $6,800 from his campaign fund, more than the mayor and three other city commissioners combined. He regularly charges parking and phone bills—including a recent $590 personal cell-phone bill—to his campaign fund, even though the city provides him a cell phone and an expense account.

Leonard defends the expenditures.

"What I'm doing is appropriate," he says. "These are privately donated dollars, and I'm using them as allowed by the law."

Janice Thompson of the watchdog group Common Cause Oregon agrees the expenditures are legal. She questions, however, whether they are appropriate.

Such expenditures, she says, "aggravate the public's troublingly low perception of government officials."

While such criticism might trouble a less confident politician, Leonard is sometimes wrong but never in doubt.

Part of the reason people don't dwell on his ethical issues is that he's forceful, funny and a master at channeling the frustrations of the average Portlander.

In addition to prodding the Water Bureau and Bureau of Development Services to improve customer service (which surveys say they have done), Leonard banned the use of duct tape to reserve parade-viewing spots, dealt with graffiti by forcing store owners to keep spray paint behind the counter, built a public restroom in Old Town to reduce public urination and thumbed his nose at Big Oil by investing a prodigious amount of city money on Oregon-brewed biodiesel.

Earlier in Leonard's City Hall tenure, strong personalities such as Katz and now-former Commissioner Erik Sten kept him partially in check. Now Adams is politically neutered, and new Commissioners Nick Fish and Amanda Fritz haven't stepped in to fill the void. Only veteran Commissioner Dan Saltzman dares tangle with Leonard, albeit ineffectually.

Katz says Leonard long ago figured out how to amass great power without seeking the city's top office.

"I asked him a couple of years ago if he would be willing to run for mayor. And he said, 'I don't have to,'" Katz recalls.

There is no better example of the way Leonard wields power than his creation of the Housing Interdiction Team.

The effort grew out of a police officer's concern in 2003 about a bad landlord in Northwest Portland.

Leonard convened code enforcement specialists from the Police and Fire bureaus and the Bureau of Development Services. They forced the landlord to sell his property.

After that success, Leonard expanded the team's scope. Working from anecdotal evidence and complaints, HIT team members began suggesting other properties.

"They identify new targets all the time," Leonard says.

The HIT team's freewheeling culture couldn't be more different from that of the process-driven Bureau of Development Services.

So far, Leonard says, the team has targeted eight or nine properties. Three were squalid single-occupancy hotels in Old Town. The city bought out the owner of the largest of the three, the Grove Hotel. Then the team went after Cindy's Adult Bookstore, also in Old Town. The city shut it down and it was razed. Next came the Greek Cusina, forced into foreclosure by HIT team liens, and a single east-side target, an after-hours club called the Mansion, which has since been demolished.

Leonard says it's difficult to define what exactly qualifies a property as a HIT target.

"It's like Justice Potter Stewart said about pornography," Leonard says. "I can't define it, but I know it when I see it."

Leonard says he personally inspects each target property.

"I make [the HIT team] call me, and I go through the building," he says.

The combination of enforcement authority from three bureaus with different enforcement mechanisms gives the HIT team a potent arsenal.

"When you combine all three, you could find just about anything," Leonard concedes.

The HIT team operated for a long time without any council oversight—not until February 2009 did Leonard's colleagues even vote on a resolution acknowledging the HIT team.

Leonard's HIT team purposely operates without a specific methodology for identifying targets.

He argues that freedom is essential. "The moment you have specific criteria will be the first time we lose the power of the team," Leonard says.

But observers increasingly worry that he wields too much power—and is accountable to nobody.

Next week: How Leonard exercises his power.

Charles Randall Leonard
  1. One of five city commissioners, each of whom is elected citywide and assigned bureaus by the mayor. First elected in 2002, defeating Serena Cruz and Nick Fish to replace Charlie Hales. Current bureau assignments: Development Services, Fire, Water.
  2. Born: Aug. 28, 1952, in Portland.
  3. Attended Grant High (class of 1970). Briefly served in the Marines but suffered boot camp injury and came home. Graduated from Portland State University in 1975.
  4. Joined the Portland Fire Bureau 1978. Portland Firefighters Association Local 43 president 1986-1998.
  5. Appointed state senator 1993. Elected state representative 1999.
  6. Four children: Kara, Kyle, Nicole and Ryan
  7. Favorite book: Cold Mountain by Charles Frazier. History buff Leonard says the Civil War novel has special resonance for him: “My great-great grandfather William G. Leonard fought for the North from Illinois and was captured and imprisoned by Confederate troops in Kentucky.”