When a snap provincial election was called in 1988 following the NDP's defeat on a critical budget vote, eight city councillors, including then-mayor Bill Norrie, announced they were considering running for the legislature.
There was so much interest among councillors, in fact, that Norrie said he was worried the 29-person council could theoretically be devastated, creating havoc in the business of civic government.
In the end, only five councillors decided to take the plunge, and three were elected -- all of them Liberals under the banner of leader Sharon Carstairs.
None of them resigned their seats during the campaign, although the winning councillors automatically lost their civic posts under rules that prohibit anyone from holding two elected positions simultaneously.
Jae Eadie, then a councillor for the Deer Lodge ward, ran for the Conservatives in St. James, but he was defeated. In an interview, Eadie said he didn't resign his council seat because it wasn't required, but he's had time to reflect on that decision and now believes it was wrong.
The question of whether councillors should resign before running for provincial office was not an issue in the election, Eadie said, except for the occasional person he met at the door who thought he was trying to have the best of both worlds.
In the provincial election of 1990, many more councillors went on to serve in the legislature, including some who held key posts in the Conservative government of Gary Filmon, also a former city councillor.
Municipal politicians have always had an incumbent-like edge when jumping to higher office because of the name recognition and personal contacts that come with the job, but Eadie said that's not why he believes they should resign.
"I think it's a question of you can't serve two masters well," he said. "Something is bound to slip."
During the 1988 election, for example, Eadie said he attended every civic meeting and dealt with every ward problem while spending every free minute on the campaign trail.
"It was too much," he said. "I was exhausted, mentally and physically, at the end of it (and) it wasn't something I intended to try again."
Councillors at that time served only part-time, but for serious members like Eadie, it was a full-time job.
In 2002, Eadie, by then considered an expert on questions of governance, was a member of a civic-provincial working group that re-wrote the old City of Winnipeg Act, now called the Winnipeg Charter.
When their work was done, the province unilaterally added an amendment that forces councillors to forfeit their seats when nominated by a party to run provincially.
"It wasn't something that had been discussed with us, even though we were supposed to be working together to update the legislation," Eadie, who was defeated as a councillor in 2006, said. "It was kind of sprung on us."
He couldn't say if the legislation was sparked by principle or politics, but others on council note that Gary Doer sat in opposition for 10 years staring across the aisle at former city councillors who dominated the suburban ridings. It's a highly cynical perspective, but the city has long complained about getting the shaft from the province.
Like others at city hall today, Eadie interpreted the new legislation to mean that a councillor would have to resign when he or she was nominated by a political party, which could be years before an actual election.
In interviews with the Free Press, however, Elections Manitoba and political staff at the province said councillors would only have to resign once they file their nomination papers, which usually occurs around the time an election is called.
Eadie said he has no problem with that interpretation, but added the legislation needs to be clarified because right now it is causing a lot of confusion and concern.
Next week, city council will debate a motion by Coun. Gord Steeves that says councillors should not have to resign until they are elected. Steeves said he believes it is wrong, and possibly unconstitutional, to disqualify a councillor from running for the provincial legislature on the grounds that he already holds elected office.
The Winnipeg Charter is unique in Canada. Other provinces leave it to the judgment of councillors and voters whether they should resign or not. In a recent case in London, Ont., for example, a councillor was elected in the city's fall election only to turn around and announce she plans to run provincially this fall. Her sudden change of heart was criticized, but the tempest quickly blew over.
As far as Eadie is concerned, the law should require politicians to quit their seats when seeking another one. "I don't think that's unfair," he said.
"It's too difficult to represent two constituencies, to do everything at the same time," Eadie said.
The city charter required Judy Wasylycia-Leis to resign to run for the mayor's job, while federal legislation forced Kevin Lamoureux to resign from the legislature to seek a federal seat, so it's not like city councillors are being picked on.