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Corruption
Applebaum was investigated by Quebec's anti-corruption police squad (UPAC) for being involved in a "stratagem of corruption" involving 10 real estate transactions and municipal contracts signed during his 2002-2012 tenure as borough mayor in Côte-des-Neiges–Notre-Dame-de-Grâce. He would be arrested at his home on June 17, 2013 on 14 charges related to two of these investigations; he was found guilty on January 8, 2017 on 8 charges, including fraud against the government, breach of trust, conspiracy, and corruption in municipal affairs.

As borough mayor, Applebaum conspired with his aides, fellow councilors, and municipal officials to extort illegal campaign contributions, bribes and kickbacks from real estate promoters and construction firms in exchange for zoning changes and municipal contracts in his borough. Applebaum was remarkably candid with his aides about his reasons for soliciting bribes: "I am not an angel ... We got to make a living." He also justified soliciting illegal campaign contributions when approaching developers in his bourough: "Elections aren't cheap".

By 2006, Applebaum was instructing his newly hired aide Hugo Tremblay to sell tickets to Union Montreal party cocktail fundraisers to promoters seeking zoning changes for their real estate projects. A box called "the hat" would be circulated at these events to collect outrightly illegal anonymous cash donations. The "pret-nom" (borrowed-name, straw man, proxy-name) scheme would be used to make it appear that large donations from a single individual came from a number of people so as not to appear to exceed Quebec's individual legal donation limits of $100. Ticket stubs would be used by Applebaum to compile lists of donors and their phone numbers for extorting "extra political effort", Applebaum's euphemism for bribes; Applebaum would then arrange to have his aide solicit and collect the bribes in cash and split the money in his car.

Applebaum would conspire meticulously to use cash in these transactions. He would instruct his aide to never discuss the cash exchanges, to accept illegal payments in a car or anonymous locations, to leave packages or envelopes in the car for a while until opening them, and to turn off any cellphones when making cash transactions. He would leave no paper trail, believing: "In order to charge you, [they] got to see the money."

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