[citation needed] Gregg has long been involved in Canadian politics, but decided to travel south of the border to work with Republican Party pollster Richard Wirthlin, and learned much from him.
He adopted a unique style including gold earrings, bright red shoes, long hair, and a great deal of leather clothing.
He also played an important role in the 1992 Canadian referendum where he crafted the message that the doom of Canada would be the certain result of a "No" vote.
[citation needed] Gregg again pushed for negative tactics, crafting an attack ad one of which Canadians found especially distasteful and offensive.
The ad ridiculed a facial deformity of Liberal leader Jean Chrétien which was a result of a childhood polio infection.
Attacking a physical defect was widely seen by Canadians as a low blow and as an American-style no-holds-barred campaign style that should not be imported.
Several years later Gregg wrote about this in the pages of Saturday Night magazine, where his mea culpa rang hollow, as he continued to argue that "the ad tested well in the focus groups."
[citation needed] After a year off, he founded a new company, The Strategic Counsel, a market research and consulting firm, but one geared towards business rather than politics.
He returned to the public eye as a columnist in Maclean's magazine and a frequent pundit on the Canadian Broadcasting Corporation news for several years.