If you get busted with a small amount of pot, it's the Seattle City Attorney who decides whether to charge you (a misdemeanor punishable by jail time and a fine) or drop the case. If you serve alcohol to a minor, the city attorney chooses whether to press charges that could land you in jail for a year or fine you $500. And when someone sues the city because his or her right to free speech has been violated, the city attorney tells city officials whether to appeal the case or concede error. The city attorney is the prosecutor in chief.

In Seattle, unlike in most cities, the city attorney is not appointed by a city official but elected by voters.

In 2001, Tom Carr won the election in a landslide. He was hailed as sweet relief compared to Mark Sidran, his anti-poor, anti-civil-liberties predecessor, who left the office to run for mayor. But Carr, despite campaign vows, has not proven himself a contrast to Sidran. Carr believes that he should continue to prosecute marijuana possession cases despite a 2003 voter-passed initiative that made marijuana possession the city's lowest law-enforcement priority. Pot prosecutions did drop—thanks to Seattle police making fewer arrests—but Carr unbelievably prosecuted a higher percentage of pot cases referred to his office.

Carr also believed that when police made 27 arrests in Operation Sobering Thought, a sting on bar employees, that he should charge each defendant with gross misdemeanors—seeking up to one-year jail terms rather than a $500 fine, which is what the Washington State Liquor Control Board does. The city attorney's office was so aggressive and sloppy about the sting that Danny Westneat wrote in the sometimes pro-nanny-state Seattle Times that this was "the nanny state gone way too far." One of Westneat's examples: police jailing "a 23-year-old bar assistant for 11 hours—allegedly for serving a drink to a drunk guy—when their own report says she 'poured him a glass of water.'" Widely regarded as a man with axes to grind who pushes a tough-on-crime agenda (even crimes citizens don't think the city should be tough on), Carr has the advantage of incumbency (he ran unopposed in 2005), name recognition, and formidable legal skills.

But a relative unknown, police watchdog Peter Holmes, who's running against Carr in November's election, is slaughtering Carr in one arena: endorsements from Democratic groups. In a two-minute speech before a crowded room of the King County Democrats on June 23, Holmes, who led the police-misconduct oversight committee for five years, blasted Carr for prosecuting low-level offenses—such as pot possession and overblown charges of obstructing police officers—while reflexively pushing unpopular cases representing the city. A few minutes later, the group handed Holmes his fourth sole endorsement in a row from local Democrats (the 11th, 37th, and 43rd District Democrats also granted sole endorsements), while Carr has received none. Several people in attendance say Carr looked dejected. Indeed, it must have been a surprise—the same group had endorsed Carr in 2001.

"We supported him big time," says Suzie Sheary, chair of the King County Democrats, regarding their Carr endorsement eight years ago. "I think Tom still has a lot of support, but Peter just has more."

It's not just that Holmes has been espousing philosophical lenience toward low-level, nonviolent crimes. He's promising to reinvent the role of city attorney. The office performs two functions: (1) prosecuting misdemeanor cases, and (2) acting as the city's lawyer, i.e., enforcing contracts and defending the city from lawsuits. Holmes argues that the city attorney works for Seattle residents and voters; if those voters don't want pot smokers to go to jail, then the city attorney should use discretion to drop charges. (Full disclosure: This is an issue that Carr and I sparred over when we were both appointed to the panel that oversaw implementation of the marijuana initiative—an initiative I organized.) And if the city is charged with a lawsuit where the city is clearly wrong, then the city attorney shouldn't waste city resources fighting it. "There is a reason why Seattle elects its city attorney when most other cities appoint the position," Holmes says. "At some point there is obstinacy, and the city attorney must be careful to consider what is in the city's best interest, rather than pursue appeals endlessly."

For instance, Holmes would not have pursued a case that the city lost in 9th U.S. Circuit Court of Appeals in late June. Balloon artist "Magic Mike" Berger sued in 2002, claiming that the city had infringed on his constitutional rights when the Seattle Center required him to purchase a permit, stand in one location in the 74-acre park, and keep "speech activities" within 30 feet of a captive crowd. Berger lost his case at first, but challenged the ruling. Carr's office fought Berger all the way into federal court—losing when a panel of judges ruled that parks are locations "where a speaker's First Amendment protections reach their zenith." Now, Carr's office is considering appealing the case to the U.S. Supreme Court. Is that what voters think the city should spend its resources on?

"I would much rather have the conversation be about the positive changes I want to make rather than criticizing Tom," Holmes says. "I think that, you know, he means well—I just think he has made numerous poor judgments over time." That's the tone coming from the Holmes camp. In an alarming contrast, Carr's campaign manager Cindi Laws is an ad-hominem-attack machine. (Laws worked on Holmes's campaign before leaving to work for Carr, a friend of hers for 19 years.) "All he knows is the upside-down end of a ledger sheet," Laws says about Holmes, a bankruptcy attorney by profession, before adding that Holmes's "only purpose in life is squeezing that last drop of blood out of a business." She argues that Holmes's years as chair of the police-misconduct oversight board was merely "grandstanding."

Meanwhile, Carr's support seems to be disappearing fast. Cleve Stockmeyer, a past candidate for the monorail board, served on Carr's steering committee in his election bid in 2001 but now supports Holmes. He points to repeated settlements in cases that the city has challenged and lost. Perhaps most egregious: Carr zealously defended the city's decision to impound vehicles driven by people with a suspended license (such as drivers who have failed to pay traffic tickets). The state supreme court tossed out the controversial law—which essentially skipped due process by seizing people's property on the spot—and a judge later ruled against Carr's office in a class-action lawsuit, ruling the city had to pay up to $1.3 million in settlement.

"I think the perception is that [Carr] is arrogant because he tends to think that this is his fiefdom and he is entitled to it," says Lem Howell, an attorney who handles civil-rights and personal-injury cases. At a campaign kickoff for Holmes in late June populated by attorneys, Howell added that, under Carr's watch, "crimes of violence are not getting the attention they deserve."

Carr's résumé is littered with other unpopular crusades. In 2007, Carr subpoenaed three Seattle Times reporters, attempting to force them to name confidential sources or face jail time (he dropped the case a few days later). The same year, he charged dozens of bar employees caught up in the aforementioned bar sting (attorneys for the defendants say that in some cases, undercover police would order drinks and hand them to underage patrons). "Carr did not investigate the circumstances around the arrests and ask himself, 'Do we have strong cases?'" says Dave Osgood, who represented three of the defendants. None of the 27 cases resulted in a successful prosecution, and, in the case of employees at Ibiza, the judge declared a mistrial after Carr's office failed to inform the employee that his testimony could be used against him. "This was nothing but political grandstanding on his part," Osgood says.

Carr believes that "the role of the city attorney is to work with the policy makers" even when those officials may be wrong, he says. But he insists he's gone "easier on low-level offenses than any other Seattle City Attorney." However, attorneys, district Democrats, and Carr's former allies think his priorities are still misplaced—and that Holmes will enact the change people thought they were getting when they voted for Carr eight years ago.