Leonard’s face would turn scarlet at the comparison, but in his nine-plus years on the City Council he’s become the George W. Bush of Portland politics. Like Bush, Leonard is a master at presenting himself as an aw-shucks everyman while cultivating close connections to his most powerful constituents. And like Bush, Leonard is adept at pushing through aggressive policies that have changed city history.

With Mayor Sam Adams badly wounded by the Beau Breedlove scandal, Leonard in 2009 and much of 2010 was Portland’s de facto chief executive. He was instrumental in bringing Major League Soccer to Portland—and at losing the 107-year-old Portland Beavers baseball team. Leonard demanded—and got—the strongest changes to police oversight in a generation. And he altered the city skyline by saving the Made in Oregon sign, changing the words to “Portland Oregon.”

And Leonard’s not finished just yet. He announced June 29 that he won’t seek re-election next year—but that leaves him with 18 months in office. Here are five items on Leonard’s to-do list before he walks out the door. 

1. CALCULATE HIS PENSIONS

Leonard insists he’s retiring with two pensions, but by our count he’ll have at least three. The first is from Portland’s Police and Fire Disability and Retirement fund from his 24-year career as a firefighter. The second is from Oregon’s Public Employees Retirement System from his 19 years as a state legislator and city commissioner. Neither the city nor the state would tell WW how much those pensions are worth. Leonard says he’ll collect about $85,000 a year—plus about $110 a month from the Veterans’ Administration for a military injury from his service in the Marine Corps, as well as Social Security from various jobs in the private sector and the firefighters’ union.

2. HELP HIS BUDDIES

Leonard says he gave “good friend” Steve Novick “several months” of notice that Leonard wouldn’t seek re-election. That tip gave Novick a jump-start in creating a website and declaring his candidacy on the day Leonard announced his departure. Two other friends Leonard could help: Adams and Police Chief Mike Reese. Leonard says he’ll endorse Adams. If Adams stays in office that will help Reese, a friend who played with Leonard in the rock band the Usual Suspects at a 2009 charity concert. When Portland mayors lose their jobs, the top cops they appoint typically go with them. Also, Leonard will need to find a spot for his personal Dick Cheney—chief of staff Ty Kovatch, whose entire career has been spent at Leonard’s side and who allowed Leonard to live in his garage while the commissioner was going through a divorce in 2009. 

3. SPEND $132,000 A DAY

Last year Leonard persuaded voters to approve a $72 million bond to pay for what critics (including Commissioner Amanda Fritz) argued is a core service that should have been covered in the city’s general-fund budget: improvements at the fire bureau. In his last 550 days in office, Leonard gets to spend the money. That includes $39 million for radios plus loads of toys like new rigs, a fireboat and a new station at the east end of the Hawthorne Bridge. “It needs to be done consistent with what we told voters would be done in the bond election,” Leonard says.

4. MOP UP THE WATER MESS

Heading the Water Bureau hasn’t given Leonard much positive material for his memoirs. In the past year he’s been slammed in a city audit for spending ratepayer money on alleged pet projects (a “Water House,” scholarships and parks among them), and he’s incurred the wrath of residents for failing to save Portland’s open reservoirs from shutdown by the feds. Now he has a final chance to chalk up a win by successfully executing the build-out of a 50-million-gallon tank on Powell Butte and a 25-million-gallon tank on Kelly Butte to replace the beloved Tabor ponds. “That’s the part of the job I won’t miss,” Leonard says of citizen ire over closing Tabor’s reservoirs. “You literally can’t win the argument.”

5. WRITE HIS MEMOIRS

Former Mayor Vera Katz has a statue on the Vera Katz Eastbank Esplanade. Another firefighter-turned-politician, former Mayor Terry Schrunk, has a downtown plaza named after him. What about Leonard? He leaves the Portland Oregon sign, a neon flower over Tom McCall Waterfront Park, and a growing number of free public commodes as the most visible reminders of his time in office. “What you learn if you actually read history is that individual people are quickly forgotten,” says Leonard, a former history major at PSU who still enjoys waxing pedantic. “It’s about how you lead your life [and] how you conduct yourself, in the final analysis, that is the legacy.” Just ask George W. Bush.

Randy Leonard Sound Bites

Clips from our June 29 interview with Randy Leonard:

• On Leonard's political alliance with Mayor Sam Adams

• On Leonard's biggest political regret

• On losing the Mt. Tabor reservoirs