6-Camilien Houde denounces conscription. Popular Montreal Mayor Camilien Houde gave a speech advising people to ignore the national registration for World War II in 1940. He vastly overplayed his hand as feds swooped in and put him in an internment camp for four years without trial.
7-Failure to extend infrastructure while it was still cheap. Highways, metro lines and other such goodies would have been relatively easy to build when the island was less built-up but would be inconceivably expensive today.
8-Building a giant public housing project in the heart of the city Mayor Drapeau passionately opposed the plan to jam a huge public housing project in the heart of the city and was rewarded for his efforts by being voted out of power. Turns out he was right as the wasteful land usage known as Jeanne Mance Housing Project has cost much potential tax revenues.
9-Money and the ethnic vote A drunk Jacques Parizeau forever burnt bridges with an important demographic when he shamed immigrants for not sharing his enthusiasm for Quebec separation following the 1995 referendum, echoing the disastrous Yvette controversy of 1976 which saw a celebrity denounce federalist women as "Yvettes."
10 The CBC Tower An entire downtown neighbourhood was demolished simply to erect a tower for the CBC / Radio Canada. The new building came with extensive tunnels underneath, making it difficult to build on adjacent lands.
11-Banning immigrants from French schools. A bizarre longstanding policy that saw all immigrants forced to attend English schools worked at counterpurpose to the demographic aspirations of the francophone majority.
12-Opposing the Cavendish extension. Cote St. Luc residents fiercely opposed any proposal to extend Cavendish to Highway 40 until they realized that the status quo was forcing them into much longer commutes, it was too late, however as authorities had lost interest in the project after they changed their mind.
13-Demolishing Goose Village. A historic neighbourhood that served as an ancient landing pad to Irish immigrants, and later Italian immigrants, once sat near Bridge street, vaguely across from where the Costco sits now. For reasons best understood by himself, Mayor Jean Drapeau ordered the entire area demolished in 1964 at great costs to the city budget.
14-Decades-long hole downtown From about 1910 to 1960 the area around Central Station sat as a massive crater, the result of the digging required for the tunnel to Town of Mount Royal. Buildings such as the Queen Elizabeth Hotel and Place Ville Marie eventually filled the space but the hole remained an open wound on the city for half a century.
15- Pastagate Quebec's infamous language policy brought much unwelcome derision to Montreal by fining a restaurant for having Italian on its menus.
16-Demolishing the Overdale block Montreal Mayor Jean Dore allowed a pair of developers to dupe him into permitting them to demolish an entire city block that they had bought up surreptitiously. They promised a shiny condo project on the site but once everybody was gone in 1989, they allowed it to sit as a parking lot, speculating on the once lively neighbourhood of students and artist and retirees for 25 years.
17-Losing the Expos Montreal lost its connection to an important vein of notereity when the team left town. Had owners held on, the team would have proved viable, as revenue sharing would have put a good profit in their pockets in spite of its low player payroll and underwhelming attendance.
18- No roundabouts Montreal's approach to traffic has long been counterintuitive, as right-on-reds have led to unnecesary pollution and delays while police enforcement of jaywalking has also led to much discomfort in cold weather, but perhaps the biggest oversight has been constantly opting for traffic lights over much safer alternatives such as roundabouts.
19- Demolition of Corridart Montreal Mayor Jean Drapeau commissioned a magnificent trail of art down Sherbrooke street for the 1976 Olympics. Some elements proved derisive to his authority so he ordered the entire thing removed.
20-Letting firetraps flourish A not-too-stringent policing of safety in bars resulted in 37 deaths at the Wagon Wheel on Sept 1, 1972. Similar oversights at the Laurier Theatre on St. Catherine in Jan 9, 1927 led to 78 young people dying, while a fire at the nearby Hochelaga school 20 years prior led to 17 young people to perish.
21-Mario Lemieux refusing to don Pens jersey when drafted. Mario Lemieux would eventually prove to be an all-time hockey great but his first connection to the NHL in 1984 would prove to be a disaster that took him many years to live down.
22-Killing of Pierre Laporte The separatist movement became associated with murder when provincial MNA was kidnapped and killed by separatist terrorists in 1970, leading to long-term damage to the movement.
23-Renaming Dorchester Various street renamings have led to unnecessary squabbles and inconvenience, in the case of Rene Levesque Blvd., it sent the signal that Montreal has to name major arteries after provincial premiers of they won't get their cookies. Had Jean Dore stood strong and resisted the temptation Montreal would have retained its independence.
24-Drapeau's restaurant Mayor Jean Drapeau, while still in power, opened a fancy restaurant with live classical music in the Windsor Hotel in 1970. The place was targeted by every stripe of protester and went broke fast, leading to a sketchy showdown that saw police illegally allow him to recover his restaurant equipment after bailiff officers showed up to seize it.
25-Removing the funicular up the hill at Mount Royal park One of Montreal's most charming features (1884-1918) allowed park-visitors to slowly wend their way up to the top of the hill until it went broke and was dismantled.
27-Celine Dion angrily declining an "anglophone song" award in 1979. In an ill advised publicity blunder, rising singer Celine Dion made a bizarre speech upon accepting an English language song award. The embarassing moment was rarely mentioned thereafter.
28-Losing the Montreal Maroons Montreal had the unique distinction of having not once, but two, NHL teams, both winning Stanley Cups. They went broke in 1938. Had the two teams stayed, it would have made
29-Shooting Anthony Griffin Montreal police officer took aim and fired at a young Anthony Griffin fleeing him in NDG in 1987. The ensuing controversy long soured relations.
30- Rene Levesque running over and killing a war veteran Edgar Trottier on 6 Feb. 1977 was on Cote des Neigs when along came the Premier of Quebec in the middle of the night. Levesque had been drinking at the apartment of his pal, the hardline separatist Yves Michaud. Levesque ran over the aged man on the street, dragged his body 140 feet. Police did not administer a breathalyzer test. Levesque's credibility and judgment were forever questioned thereafter.
31-La Cite Great numbers of classic old buildings in the Milton Park area of the McGill Ghetto were demolished for the La Cite project, as authorities overlooked a huge movement to protect the area.
31-Setting the great fire of 1852.About half of Montreal burned in 1852. Someone carelessly allowed flames to spread from a fire on St. Lawrence.
32 - Bombing 11-year-old Daniel Desrochers Montreal's biker war was allowed to continue without much interruption until a poorly-planned bombing killed a child in the east end. Authorities swiftly intervened to enact new laws to take down the gangs.
33-War on gays Police led major busts against gays in Montreal bars, tossing people in jail routinely until the late 1960s and then ramping up the effort with the Truxx raid in 77, Buds in 84, Sex Garage in 1990 and Katacombes in 1994.
34-Eradicating streetcars Montreal's longstanding love affair with streetcars ended in the mid-1950s when all of the beautiful old trains were tossed in a big fire. Saving a few of the lines would have maintained some of the charm they offered.
35-Souki Montreal Expos unveiled a mascot in 1978 that lasted only one season as the round-haired scourge struck fear into the hearts of children.
36- Not saving the Van Horne Mansion Business owner David Azrieli took advantage of lax demolition laws to raze a venerable old mansion on Sherbrooke in 1974.
37-The De Bernonville petition 143 Quebec notables signed an ill-advised petition urging Canada to allow an infamous French war criminal to stay in Canada. De Bernonville was a particularly bloodthirsty killer who was forced to Brazil where he was killed by his servant's son in 1972.