Testifying before a Chicago election board official during a hearing that was sometimes funny, contentious and downright strange, Emanuel defended himself against claims by opponents who say he is not eligible to run for mayor in February's election because he moved out of the city to take a job as Obama's White House chief of staff.
Speaking in a quiet voice, his hands clasped before him and a photograph of his family in front of him, Emanuel looked and sounded nothing like a politician widely known for his tough, take-no-prisoners and often profane style.
Throughout the day, he appeared relaxed and smiled easily, once joking as his income tax returns were shown on the screen in the room that, "It does call for tax reform, I'll tell you that."
And he laughed when one of his questioners, a community activist, signaled he was out of questions when he joked, "Have you ever been a member of the Communist Party?"
"I enjoyed that," Emanuel said.
But Emanuel also addressed the issue of his leaving Chicago with what his attorneys and supporters believe is powerful evidence he fully intended to return.
He listed the family's "most valuable possessions" that he left in his house after he and his family moved to Washington, D.C., in 2009, including his wife's wedding dress, clothes his children wore home from the hospital just after they were born, photographs, his children's report cards and their drawings.
He made special note of leaving behind a coat that his grandfather gave his father a half century ago.
"It's the only possession I still have from my grandfather," he said.
He repeatedly came back to a theme he has been sounding throughout his campaign to succeed the retiring Mayor Richard Daley: He only left his job as a Chicago congressman and moved his family to Washington to work for the president.
After about nine hours of testimony, Emanuel began taking questions from his own attorneys.
He testified he never thought about making any place other than Chicago his permanent home and said "it never crossed" his mind that he might not satisfy the residency requirement to run for mayor.
"Having been a congressman elected four separate times, having been born here, having raised my kids here, having owned a home in the city of Chicago . the only reason, the only reason I left the city of Chicago was to take an appointment at the request of the President of the United States to serve as his chief of staff," he said.
Emanuel, who knows that if his name is allowed on the ballot he will have to battle opponents' argument that he is not really a Chicagoan like them, tried throughout the hearing to draw a distinction between his life in the two cities. He repeatedly used phrases like "back home to Chicago," and when he talked about his residence in Washington, it was always a "rental property."
But opponents of Emanuel's candidacy, who claim he forfeited his residency when he moved and rented out his house on the city's North Side, argue none of that matters. They say the law is clear: To run for mayor, a person has to be a resident of the city for a year prior to election day and Emanuel, who moved back to Chicago in October, simply does not qualify.
During the hearing, they peppered Emanuel with questions about his income tax returns, driver's license, voting record and car registration that were designed to suggest he was no longer a Chicago resident.
But Emanuel, as he has said throughout his campaign, talked about how he registered to vote from Chicago and voted absentee, did not sell his house and continued to pay Illinois taxes.
He also responded to opponents' contention that by renting his house he was no longer a resident of the city, explaining that he and his wife did so on the recommendation of real estate professionals "for the safety and security of the house."
The hearing got progressively stranger as the day went on and the attorneys gave way to Chicago residents who filed objections to his candidacy. One of those, a man named Jeffrey Joseph Black, had fellow objectors shaking their heads when he asked Emanuel if he caused the 1993 siege at Waco, Texas, or knew about his supposed FBI file called "Project Mega" or "Mega File."
Another, a woman named Zakiyyah Muhammad, wanted to know what role Emanuel played in the U.S. Agriculture Department's request that Shirley Sherrod leave her job as Georgia's director of rural development after comments she made in March were misconstrued as racist.
The hearing officer ruled Emanuel did not have to answer those questions, saying they were inappropriate.
The hearing was expected to continue into Tuesday night and on Wednesday. Also scheduled to testify is Rob Halpin, the man who rented Emanuel's house and refused to break the lease so he could move back in. Halpin made headlines when his refusal became public and with his own short-lived run for mayor, which he abandoned a few weeks ago.
A decision will be made within days because officials have said they need to settle on the list of candidates well before the Feb. 22 election.