J. Wyndal Gordon has spent the last nine months calling Michael Brown a rat, but on Monday, he felt sorry for him.

Gordon, an outspoken Baltimore attorney who calls himself the “warrior lawyer,” represents Hakim Sutton, who served as Brown’s campaign treasurer until the former at-large councilmember fired him and accused him of embezzling campaign funds last summer. So Gordon has plenty of reasons to enjoy the downfall of the man he once declared to be of “morally depraved composition.” But after watching Brown plead guilty Monday to accepting bribes in 2012 and 2013, Gordon pegged his mood differently—-“melancholy.”

U.S. Attorney Ron Machen, on the other hand, was livid. This wasn’t the bank fraud of former Council Chairman Kwame Brown, whose scheme started in 2005 and thus couldn’t be a reflection on Machen’s effectiveness at scaring officials onto the right side of the law. Apparently, Brown felt he could solicit bribes right as federal law enforcement was on a well-publicized push to straighten out the District’s government.

Brown started searching for a deep-pocketed, ethically compromised contractor even after Machen had repeatedly warned Washington politicians to clean up. His first bribe by undercover FBI agents came just a day after Jeanne Clarke Harris pleaded guilty for her actions in the 2010 shadow campaign to elect Mayor Vince Gray, a coincidence that wasn’t lost on Machen.

“It is clear many people have not gotten the message,” Machen said at a press conference Monday, after Brown’s plea.

Machen used the opportunity to dish out another round of boastful threats (or are they threatening boasts?). “If you believe you’re too smart or your scheme is too complex, you’re wrong,” Machen said. “These prosecutors are not only very persistent, they’re very good at what they do.”

Machen’s constant admonitions—-and his appearance in last October’s issue of Washingtonian, where he looked ready to leap over his desk and clothesline a sticky-fingered official—-show he’s hoping persuasion can be as effective as prosecution in cleaning up D.C. politics. But Brown’s plea Monday showed it isn’t working on everyone—-and it’s time for the U.S. Attorney and the people he’s trying to serve to wonder why.

Brown wasn’t only pleading guilty to bribery and accepting a potential 37 months in prison, under a deal reached with prosecutors. He was also accepting responsibility, less formally, to being desperate enough to fall for a whopper of an FBI sting.

Brown’s undoing didn’t come from the kind of elaborate shadow campaign or straw donor schemes that have made headlines in the District over the past year and a half. Instead, Brown took $55,000 in bribes from undercover agents from July 2012 to March 2013 in laughably obvious ways—-inside a Pigskins mug, or in a duffel bag along with complimentary Nationals T-shirts (all of it caught on video released in still images to media, of course). Heck, at least Ward 5 Councilmember-turned-federal prison camp resident Harry Thomas Jr. hid his misdeeds behind a nonprofit.

Brown was supposed to be helping the agents, who were posing as Maryland businessmen, get into the Certified Business Enterprise program, which is meant to aid local, minority- or women-owned firms in obtaining District contracts. He spends much of the events recounted in court documents coining a new patois of Washington corruption: An advance on the rest of the bribe was a “piece of the piece,” and progress toward the certification meant they were “moving and grooving.” The details of the sting read like they were dreamt up in an escalating series of dares between the FBI and the U.S. Attorney’s Office: Just how brazen will these councilmembers be?

Brown spent the last few years transforming himself into the perfect mark for the feds. He faced financial problems, including a tax lien, an ongoing divorce, and a $1.8 million Chevy Chase house he still can’t sell. A year ago, Brown claimed that he discovered $110,000 missing from his re-election fund, which he blamed on Sutton, his treasurer. (The alleged embezzlement is still being investigated.) “Like many people after the economy crashed, Michael had extreme financial pressures, and they caused him to make a very unwise decision,” Brian M. Heberlig, one of Brown’s attorneys, said outside the courthouse.

Brown’s predicament should be enough to spook any councilmember. Longtime rivals were there to watch him finish the career collapse that started when he lost his November re-election bid, then was forced by law enforcement to drop out of April’s special election. Gordon was joined by District gadfly Marie Drissel, who spent countless months foiling Brown’s online gambling legislation, and reporter/activist Dorothy Brizill, whose petition challenge became yet another headache for Brown’s November campaign. LL is sure he heard Brown choke up while U.S. District Judge Robert Wilkins quizzed him about the plea, and who can blame him?

Despite all that, Machen’s first major D.C. catch since Harris’ plea nearly a year ago didn’t exactly send shockwaves through the Wilson Building. Brown’s guilty plea surprised many, but it hasn’t changed the wait-and-see attitude of Machen and Gray, according to one administration official who wasn’t authorized to speak on the record and requested anonymity.

“There’s more of a feeling that Machen has never gone away, versus ‘Machen’s back,'” the official says. “We knew that he would be around until the investigation’s concluded.”

There’s something else muddling Machen’s lawman image: the two elections Brown ran in while on the take. By the time he finished third behind Vincent Orange and David Grosso for the two at-large seats, Brown had already accepted three payments worth $35,000 from the FBI agents. They had him on tape talking about how close he was to getting them to the fraudulent CBE certification. (“Damn right, it came through quick.”) But the U.S. Attorney’s Office didn’t intervene.

The FBI had even more in January, when Brown announced his intention to get back on the Council by running in the April 23 special election for the seat previously held by Council Chairman Phil Mendelson. The investigation had accumulated Brown’s frantic text messages and phone calls for a “piece of the piece,” and had recorded this instant classic of Brown’s cynical wheeling-dealing: “It’s not cheap to get people on top of the pile.”

Still, law enforcement didn’t force Brown to leave the race until early April. It’s easy to see how the presence of a well-connected former councilmember in the campaign could have scared off potential challengers, altering the dynamics of the race and, perhaps, its ultimate winner, incumbent Anita Bonds.

If Brown hadn’t lost to Grosso in November, or the U.S. Attorney had taken a little longer to put together a case before April, the District might have found itself footing the bill for yet another special election. They don’t come cheap—-D.C. Board of Elections director Clifford Tatum asked for more than $1 million for April’s, the third since the 2010 election.

On Monday, Machen defended his decision not to go after Brown until he felt the ex-councilmember was fully ensnared. “If we had brought that case down earlier and, Lord knows, we charged him and didn’t get a conviction, everybody would say ‘What’re you doing?'” Machen said. “‘Influencing an election by charging somebody before you have all the evidence?'”

Brown’s November loss lessened the impact of the bribery sting. Another indictment of a sitting councilmember would have brought on another round of the spectacle Machen needs to show he’s serious: a hasty resignation, followed by an escape from the Wilson Building in a storm of thrown elbows.

“Had [Brown] been here, it would’ve been a zoo,” one Council staffer predicted to LL. Instead, the District saw the downfall of a man who was starting to look like a political loser anyway.

Judging from the abyss of disappointment he brings to each new guilty plea, Machen has grander ambitions for the District and for himself. The prosecutor declared Brown’s influence peddling the product of a “broken system” that allows councilmembers to influence city contracts. Now that he’s called it broken, it’ll be hard for Machen to avoid trying to fix it. The only way there goes through the investigation that kicked off the District’s recent tumult in the first place: the shadow campaign behind Gray’s 2010 election and its alleged money man, accountant Jeffrey Thompson.

Brown’s plea puts Machen a little closer to Thompson. In addition to the bribery charge, Brown’s plea deal involved admitting to taking illegal contributions in his failed 2007 run for the Ward 4 Council seat from an unnamed Washington businessman who, as described in court papers, resembles Thompson. Because the businessman wanted to back multiple candidates in the race for the benefit of his enterprises, he sent Brown $20,000 in wire transfers via Harris, a longtime Thompson associate, according to Brown’s statement of offense. Brown, in turn, disguised the money as his own contribution to his campaign. (Interestingly, Brown wasn’t charged with any campaign finance crimes in court, despite admitting all that.)

Machen declined to comment on who Harris and now Brown are giving up to the feds, but we may not have to wait long to find out. On Monday, prosecutors asked for extra time before sentencing to ensure that he would cooperate with other investigations. Brown’s sentencing is set for Oct. 3. By then, we should know whether Machen can still back up his bluster.

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Photo by Darrow Montgomery