Michael A. Brown talks to Council member Harry Thomas, left, before a Council meeting. Campaign officials from 2008 say their experiences offer a window into the troubles Brown is facing now (Astrid Riecken/FOR THE WASHINGTON POST)

Less than two months before the November 2008 D.C. Council elections, Michael A. Brown’s campaign manager, finance director and top field staffer approached him at a fundraiser on Capitol Hill and quit.

They blasted what they called his dysfunctional management style and told Brown he was lazy, according to interviews with two of the men. They said they told him they couldn’t deal with the bounced checks, the missed payrolls and the disgruntled staff.

“I had reached my limit,” said Lewis Thomas, who managed the independent candidate’s bid for an at-large seat from May until September in 2008. “He wouldn’t show up to events, would come to events late, and didn’t want to do the work because he has the strongest sense of entitlement that I have ever seen . . . and the greatest form of arrogance I have seen.”

In interviews, nearly a dozen people affiliated with the 2008 campaign voiced similar concerns: Brown was aloof, a poor manager and had trouble keeping his campaign finances in order.

Brown won the race. But those campaign officials say their experiences offer a window into the troubles Brown is facing now, as he runs for reelection — a run that has been marred by an audit that shows that more than $100,000 is missing from his campaign coffers, and a very public dispute with his former treasurer as to who is to blame.

Brown, the son of late commerce secretary Ronald H. Brown, declined to address the criticism from his former staff. “I’ m not going to comment on the past campaign. I’m worried about this campaign,” Brown said.

But Asher Corson, Brown’s spokesman, released a statement later questioning the motives of the former staffers.

“It is unfortunate that four years later, former disgruntled campaign workers are taking their gripes to the media,” Corson said.

The criticism brings to the surface a trail of ruined relationships between Brown and many of the political professionals who helped put him in office four years ago. The public criticism is rare, as many of these officials’ livelihoods depend on solid relationships with politicians.

“He has just been horrible across the board,” said Julius Henson, a Baltimore-based Democratic strategist who took over when Thomas quit. “Every political bridge, every supporter who has helped him, I don’t know anybody who would be willing to help him today.”

Brown is competing in the Nov. 6 election against six other candidates for two citywide council seats, one of which is reserved for a non-Democrat.

Although Brown is favored, his opponents are trying to persuade voters that his personal issues — including struggling to pay his taxes, mortgage and rent on time, and five suspensions of his driver’s license over the past eight years — should disqualify him from the job. His opponents also say that Brown’s oversight of his campaign should be an issue for voters, particularly as a federal investigation into the 2010 campaign of Mayor Vincent C. Gray (D) has clouded Gray’s administration.

In 2009, after Brown defeated five other candidates, an Office of Campaign Finance audit found that he failed to properly document nearly $100,000 in contributions or loans, about $155,000 in expenditures, and bouned $80,000 in checks.

Several of his former aides say the audit shows that Brown struggled to oversee a well-disciplined campaign long before he went public this summer with accusations that former treasurer Hakim Sutton took $113,950 from his 2012 campaign. Sutton, through his attorney, denies that he took anything and says that Brown authorized the payments and asked him to hide them.

“The only thing I can say, the pattern that he is following now, follows his other campaigns,” said Gerri Adams Simmons, chairman of Brown’s 2008 campaign. Simmons became disillusioned after she said Brown broke a promise to make her his council chief of staff. “Anyone looking at it, wondering why these things keep happening, look at what is central to all of that.”

After unsuccessfully running as a Democrat for mayor in 2006 and the Ward 4 council seat in 2007, Brown launched his at-large bid in spring 2008 after becoming an independent.

Thomas, a Philadelphia-based strategist brought in to manage the campaign, said within weeks “it was pretty clear there were some major, major issues” with Brown’s oversight.

“He was generally never on time for anything and didn’t take it seriously when he was there,” recalled Jeff Yurcan, Brown’s first finance director in 2008, who left with Thomas that September. “He was kind of like, he was just going to sit around and let us get him elected.”

Yet with access to a local and national network of supporters with fond memories of his father, who died in a plane crash in 1996, Brown managed to raise hundreds of thousands of dollars.

But the former aides say the campaign struggled to keep track of how the money was spent and suffered from poor documentation. Henson and Thomas pinned part of the blame on what they called a blurred wall between Brown’s campaign and personal finances.

The 2009 audit revealed 17 campaign expenditures totaling $9,139 that were not paid out of the committee’s bank account, as well as seven checks totaling $16,042 that were improperly made payable to cash. According to an OCF review of bank statements, Brown had also loaned his campaign $25,265 without reporting it in a timely manner.

Brown eventually reconciled his campaign finance reports. But OCF officials said they could not provide supporting documentation with their audit because they turned those records over to the U.S. attorney’s office at its request in February. A spokesman for the office, which earlier this year requested fundraising records for several council members, declined to comment.

Henson, who specializes in urban races, said the Brown campaign often had to use cash — sometimes directly from Brown’s pocket — to pay its bills because it had so much trouble preventing checks from bouncing. Forty-nine bounced checks were documented in the audit.

“I have never been on a campaign that had that much financial discombobulation, and I believe it’s because of the candidate,” said Henson, who spent one month in jail this summer after he was convicted of conspiracy to violate campaign laws when he worked on former Maryland governor Robert L. Ehrlich’s (R) 2010 campaign. “If there was a lady working in the office who hadn’t been paid, he would go into his pocket and pull out $400.”

Henson, Simmons, Yurcan and Thomas all said they were not surprised by Brown’s dispute with Sutton over the missing funds this year.“No one who has worked for Michael seems to have a good time,” Yurcan said.

Mike DeBonis contributed to this report.