When Tim Mahoney (D-FL) announced his bid for Congress in 2006, he had little reason to expect he would win. He was running against a popular incumbent in a safe seat. When Mark Foley self-destructed he wound up a surprise winner, and it was only a few months before the former businessman publicly complained about not liking his job, even though (we now know) he had a girlfriend on his payroll. According to a contemporaneous press account, Rahm Emanuel confronted him in May, 2007 — allegedly about his disillusionment with public life. But within a few weeks, his flame was off the payroll. That begs the question: exactly what did Rahm Emanuel talk to Mahoney about?

According to the Associated Press, Tim Mahoney’s romantic relationship with Patricia Allen began during the 2006 campaign:

The FBI is investigating whether Democratic U.S. Rep. Tim Mahoney broke any laws or misused federal money when he hired a mistress to work in his office, a senior federal law enforcement official told The Associated Press.

Federal agents also are examining whether a second affair Mahoney was having with a high-level official in his Florida district was behind his decision to push for federal emergency funds for her county, the official said…

The FBI is looking into whether Mahoney hired the first mistress — and put her on the federal payroll – so she wouldn’t reveal their affair, the person said. The woman, Patricia Allen, has not returned repeated calls.

Mahoney, 52, who is married with a child, began his affair with Allen, 50, in 2006 while campaigning for Congress.

The online Congressional database Legistorm reports that Allen was on Mahoney’s payroll from his first day in Congress, and stayed on the payroll until June 2. Those first 6 months were a trying time for Mahoney. He was seen as unhappy in his job and poorly matched for the role of Congressman. He clashed with his colleagues. He even expressed his disappointment in his job, even going so far as to tell The Hill ‘this isn’t the greatest job I’ve had.’ That story in the Hill came out on May 24, 2007, and it also reported that Mahoney had been confronted by House Democratic leaders — including Rahm Emanuel:

The millionaire Florida businessman has shrugged off advice from some seasoned lawmakers and exhibited an impatience for the glacial pace of Congress, prompting Rep. Rahm Emanuel (D-Ill.), the Democratic Caucus chairman, to have a quiet tête-à-tête with arguably his most vulnerable freshman, according to several sources, including one Democratic lawmaker.

Mahoney denied that a Democratic leader had confronted him, but said, “I think there was a concern that I wasn’t happy in Congress. Very candidly, this isn’t the greatest job I’ve had.”

Mahoney was causing enough worry about whether he could cope in Congress that the Democratic leadership tapped a prominent Washington insider, Chuck Brain, to act as an informal adviser, according to a Democratic lobbyist. Now the head of his own lobbying firm, Brain was a longtime congressional staffer who served as the Clinton White House’s chief liaison to Capitol Hill…

“I’m trying to do what I can for the Democrat who is perceived by Republicans to be the most vulnerable,” he said. Davis said that both he and Emanuel pointed Mahoney toward Brain after the freshman came to Washington “because we know how good Chuck is…”

So Rahm Emanuel took an early interest in Mahoney, spoke to him about his troubled early tenure, and appointed a ‘mentor’ to guide him through troubled waters. And just a week after this story appeared in The Hill, Allen was off of Mahoney’s payroll. What happened next? Emanuel threw a fundraiser for him:

Meanwhile, the Democratic leadership is firmly behind Mahoney: Emanuel and House Majority Leader Steny Hoyer (D-Md.), along with Financial Services Committee Chairman Barney Frank (D-Mass.), are hosting a fundraising event for him next month.

There’s no smoking gun here, but the timeline is awfully suspicious. Are we to believe that in all the conversations that Emanuel had about Mahoney — both with colleagues and with Mahoney himself — the fact that he had a flame on the payroll never came up? And despite having selected a trusted lobbyist to guide Mahoney, Emanuel never came to learn about the violation until the last few weeks?

I call shenanigans.

Now the real question: who’ll ask Rahm Emanuel what he knew, and when he knew it?