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It was February, 2012, and George Christopoulos was new to the toughest job in Toronto: press secretary to Mayor Rob Ford. Reporters were questioning the mayor about a dramatic vote by city council to overturn his subways plan, which lacked hard numbers, and build light-rail transit instead.

"Technically speaking, that whole meeting was irrelevant," Mr. Ford said, dismissing the verdict of the city's chief legislative body. Like a bodyguard protecting his man, Mr. Christopoulos stepped forward, raising his hand to try to cut off questions. "Okay guys, thank you," he said. Spectators jeered and laughed. Mr. Christopoulos retreated.

It was the beginning of what must have been a devilishly frustrating time for the former reporter and police spokesman. He had the impossible job of managing the press relations of a man who refused to be managed. When Mr. Ford dropped out of sight, showed up late or did something outlandish again, Mr. Christopoulos had to field the questions.

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To do his job, a press secretary has to know at all times where his boss is and what he is going to do or say. With an unpredictable boss like Mr. Ford – and worse, his shoot-from-the-lip brother, Councillor Doug Ford – he often had no idea. The Fords freelance their press relations. They even have their own radio show.

It put Mr. Christopoulos in a tough position. He was discreet and loyal, but if you asked him how things were going, he would give you a look that said, "You can't imagine."

In recent weeks, as the sense of crisis in the Ford camp grew, he faded from view. Often, he would not even answer messages about the latest twist in the ongoing drama. Now, suddenly, he is out.

Just after lunchtime on Monday, it became clear that something big was up. The mayor was seen walking purposefully down a corridor in City Hall with the head of security and the city manager. Then he walked into the office of Mr. Christopoulos. No one was there.

The press chief and his deputy, Isaac Ransom, had resigned, stripping the mayor of one of his top aides and adding to the impression that the wheels are coming off the Fordmobile.

The mayor did his best to sound in control when he came out of his office to meet reporters a little while later. "It's business as usual," he said. Nothing happening here, folks. Move along now.

He suggested that Mr. Christopolous was leaving for no other reason than that something better came along. "I'm not going to hold anyone back from moving on for future endeavours or opportunities that they may have," he said. If anyone in his employ has a bigger job lined up, he said, he always tells them: "Go. Please take advantage of it."

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Nice try. Press secretaries do not generally leave in the midst of a crisis by dropping off a letter and clearing out their office before the boss gets to work. The whole city – no, country – knows Mr. Ford's administration is in utter disarray. Mr. Ford has lost his chief of staff and his press secretary in the space of a week. The Office of the Mayor, always short-staffed under the cost-cutting Mr. Ford, has been weakened even further. His chief of operations and logistics is long-time family associate David Price. A former member of his high-school football team just signed on as a "special assistant," joining another former Ford-team player on the staff. His new press aide, Amin Massoudi, graduated from Queen's in 2010 with a BA. As assistant to Doug Ford, he could often be seen driving the councillor's big black SUV.

If ever a public figure needed strong, impartial advice, it is Rob Ford. But, if former staffers are to be believed, he simply does not listen. He has gone through three chiefs of staff and two press secretaries since taking office in December, 2010. Who will be next to go?

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