Key events in Phil Sheegl's 5 1/2 years as a senior official with the City of Winnipeg:
- Arrival at city hall
In a surprise decision, Winnipeg real-estate agent and Arizona property developer Phil Sheegl is chosen to fill a vacancy at the helm of the city's planning, property and development department in April 2008. Mayor Sam Katz said he tried to talk Sheegl -- whom he described as a good friend -- out of applying for the job. "I wouldn't wish that grief and aggravation on anybody, let alone a friend. But as you can see, he didn't take my advice," Katz said at the time.
- Riverside Park affair
In September 2008, the city's planning, property and development department recommended retroactive changes to a lease of a city-owned parking lot to Riverside Park Management, a company that sublets land to the Winnipeg Goldeyes, owned by Mayor Sam Katz.
Those changes allowed Riverside to avoid a bill for $233,000 in unpaid rent. City council eventually approved the controversial plan.
- Swift ascension
Six months after he arrived at city hall, in October 2008, Sheegl is promoted to the position of deputy chief administrative officer and effectively becomes the second-most-powerful public servant at 510 Main St.
- Police HQ deal
In March 2009, the Deputy CAO brokers a deal to purchase the former Canada Post building on Graham Avenue and convert the structure into new headquarters for the Winnipeg Police Service. The plan initially comes with a $135-million pricetag - but later balloons to $194 million.
- Parker land swap
In July 2009, the city reveals a Sheegl plan to swap unserviced city land in the Parker neighbourhood in Fort Garry to developer Andrew Marquess in exchange for a smaller parcel of serviced land at the Fort Rouge Yards, alongside the first phase of the Southwest Transitway. The Parker land is later selected to accommodate the second phase of the transitway.
- Into the CAO's office
Following a nationwide search for a new chief administrative officer, Sheegl is selected to lead Winnipeg's public service in May 2011. Five councillors voted against the promotion, warning against having a friend of the mayor in the city's top job.
That fall, Sheegl installs a statue of the three wise monkeys outside the entrance to his office, sparring complaints the "see no evil, hear no evil, speak no evil" message sends an inappropriate signal about the upper echelons of city hall.
- A disastrous 2012
After the failure of a plan to build a hotel and water park at The Forks - at the same parking lot once leased to Riverside Park Management -- members of council question the oversight of the public service in the spring.
Those voices grow louder in the late summer, when it's revealed the city built a new fire-paramedic station on land owned by Shindico Realty -- and planned to acquire that land by swapping two old fire halls and a patch of riverfront land in Fort Rouge.
While Sheegl claims to only be aware of the plan "at 50,000 feet," the ensuing scandal sparks both a review of the city's fire-paramedic station replacement program and a broader audit of city real-estate transactions.
Council is further enraged when it's revealed Sheegl sold an Arizona shell company to Katz and reacquired it weeks later. Couns. Ross Eadie (Mynarski) and Russ Wyatt (Transcona) become the first to call for the CAO's resignation, with Wyatt suggesting dismissal if Sheegl does not resign.
- Tempest in a parking spot
After the closure of the Civic Centre Parkade in 2012, Sheegl began parking his personal vehicle at the top of a loading ramp at the rear of city hall's administration building -- at a time when other officials were forced to find parking spots further afield. Maintenance work on that ramp later forced him to park on a stretch of James Avenue reserved for police vehicles, already displaced by the parkade closure, a symbol of crumbling infrastructure only one block from city hall.
- End of the line
In September 2013, weeks before the release of the fire-paramedic station review, fire-paramedic chief Reid Douglas is fired without explanation. Angry councillors resume a move to remove Sheegl from his post, with Eadie reviving a motion that would have come to council next week.
In what appeared to be a pre-emptive move, Sheegl resigned on Thursday.
-- Bartley Kives