In November 2012, Michael Applebaum was poised to make history as Montreal’s first Jewish mayor and its first anglophone mayor in over a century.

But his friend and former chief of staff, Hugo Tremblay, had his doubts about Applebaum’s campaign to become the squeaky-clean mayor who would “erase the stain” of corruption tarnishing Montreal.

“I tried to convince him (not to run),” Tremblay told a court Monday. “The way he was going about it would just multiply the number of enemies we would have, and I knew there were skeletons in the closet.”

Applebaum ignored the advice, and seven months later the closet door would be burst open when anti-corruption police arrested him at home. On Monday, the friend turned informant was the first Crown witness at Applebaum’s trial on 14 charges of fraud, breach of trust and conspiracy.