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In November 2008, Robertson came under scrutiny after reporters discovered that he had an unpaid transit infraction fine from the Sky Train system.
While the public generally appeared willing to accept his explanation that the original infraction was a mistake, he was criticized by some for attempting to spin his failure to pay into a politically positive statement. He was elected by a solid margin in the 2008 municipal election.
In July 2010, Robertson was caught on an open microphone referring to speakers from the public at a council session as, "Who are all these fucking..are these hacks, man? " Robertson and Councilors Tim Stevenson and Heather Deal went on to mock and laugh at the speakers who had called for greater transparency in the selection of a 12-person committee that will advise council on rezoning.
In 2017, the city announced its proposal of a new logo.
Community residents cited concerns with lack of public consultation, fights, public urination, defecation, public sex, and open drug use.
Later that year, Penny Ballem, the unelected city manager, notified council about a federal proposal from the Mental Health Commission of Canada to address the homeless crisis by turning the 102-room low-budget Bosman's Hotel on Howe Street near Helmcken Street into an experiment designed to see if aggressive health treatment along with housing could help the same target population.
However Robertson lost support from a former Vision Vancouver executive board member, who resigned from Vision Vancouver on May 7, 2009 and stated he was encouraging other members to do the same, based on his claim that Robertson had not responded to a message the member had sent regarding his concerns about the Campbell remarks. But given that we’re so close to an election, some of my comments were misconstrued by people." On May 19, 2009 Robertson sent a congratulatory letter to Campbell with a handwritten note that started with "Congrats" and continued, "looking forward to a very productive run-up to the Games and a strong partnership for Vancouver’s future!
The idea was described by graphic designers as "Uninspiring and a huge missed opportunity at rebranding the west coast metropolis." According to the CBC, Robertson lost his temper when asked about the logo. On April 9, 2009 a member of Robertson's Vision Vancouver caucus, Geoff Meggs, stated that Robertson regretted the language he used as being "unguarded" and that it was intended to build a relationship with the governing provincial party.
Gregor Robertson came to mayorship at a time in history when cities worldwide had been installing advanced cycling infrastructure.
This caused him to be associated with cycling in media and the public eye.
Council will decide on the proposal in the Fall of 2009.
On September 15, 2009, Vancouver city staff issued a report warning Mayor Robertson and the City Council that they should no longer expect the HEAT shelters to be funded after the 2009–2010 fiscal year.