Last week, he was the subject of "I [heart]ary Webster" buttons.
Next week, he could be out of a job.
The TTC has scheduled a surprise meeting for Tuesday to debate Mr. Webster's future at the agency, just two weeks after the long-time chief general manager sparred openly with Mayor Rob Ford's team over the future of rapid transit in the city.
Five Ford allies on the nine-member commission signed a letter calling for the meeting: Denzil Minnan-Wong, Norm Kelly, Frank Di Giorgio, Vince Crisanti and Cesar Palacio.
Due to staff confidentiality issues, none would elaborate directly on Mr. Webster's job status.
Mr. Di Giorgio, however, did acknowledge that the snap meeting stems from the obvious tension between Mr. Webster and the mayor.
"If I'm a top member of the bureaucracy and I can't support a new mayor's mandate, I should either resign or find a new position or approach," he said. "I should not actively work against the mayor's mandate."
Mr. Di Giorgio refused to confirm that commissioners plan to oust Mr. Webster, a course they can take with a simple majority vote.
"We want to re-examine the situation that's happened over there and come to grips with how to make things work more harmoniously," he said. "If we can't, then we'll have to take some steps. I don't know what the group will decide on but we will be discussing a couple of options."
A 35-year veteran of the commission, Mr. Webster worked his way up through engineering positions at the agency to take the top post in 2006, the first chief general manager hired from within the organization.
Ford allies have said they want a business-oriented outsider to take over and clean house at the commission.
But one current commissioner said she won't go along with the shakeup.
"I'm in shock," said Councillor Maria Augimeri. "I think the people who signed this letter are spineless cowards who don't care for the integrity of the people we serve."
Rumours of Mr. Webster's dismissal have swirled through City Hall since the summer but came to a head during a council meeting last week where he offered a passionate indictment of Mayor Rob Ford's subways-or-bust transit plan.
"We don't recommend spending the money you don't have on an asset you don't need," he said of subways that day, which ended in Mayor Ford's biggest political defeat since taking office, a 25-18 vote against his subway plan.
Councillors decided instead to resurrect a David-Miller-era scheme to build above-ground light rail on Sheppard Avenue, Finch Avenue West. and at the east end of the Eglinton Crosstown line.
It was then that buttons bearing the phrase "I [heart]Gary Webster" began appearing around City Hall.
Following the meeting, TTC Chair Karen Stintz, who led the insurrection, acknowledged that it would have consequences for herself and Mr. Webster.
Mr. Webster earned $281,931 in 2010. Former TTC vice-chair Joe Mihevc said his dismissal would cost the city hundreds of thousands of dollars. "And it's such a waste because he's such a good manager," Mr. Mihevc said.
"This is an absolutely abhorrent way to run a city."
The mayor was at City Hall on Friday but refused to take questions from reporters.
Commissioners will meet in private at 2 p.m. on Tuesday. Public feedback is scheduled for 3:15 p.m.