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In the last municipal election, Toronto Councillor Paula Fletcher won by several hundred votes and is hoping to keep her Ward 30 seat in October. Fletcher is photographed on the rooftop deck at Bridgepoint Active Healthcare on Sept. 5, 2014.Fred Lum/The Globe and Mail

It was one of the tightest races of the last municipal election: Veteran Councillor Paula Fletcher hung onto her east-end ward by just 259 votes after a strong challenger's late entry to the campaign.

Fast-forward four years and that same rival, television host Liz West, is vying again for the top job in Ward 30 Toronto-Danforth. But this time around, there is another viable contender, former CBC Radio broadcaster Jane Farrow, who this week landed the endorsement of former federal Liberal leader Bob Rae, whom she knows through a family connection.

The dynamic race is shaping up as one of the city's most-watched local contests. After a term rocked by discord, both of Ms. Fletcher's main challengers argue a fresh face is needed to better represent residents at city council.

The race took on an edgy undertone this week, with anonymous "Give Paula the Pink Slip" flyers appearing in mailboxes attacking Ms. Fletcher's attendance record. "It's a smear campaign," Ms. Fletcher says, adding she hasn't missed any major votes. Ms. West and Ms. Farrow say their teams were not involved. Similar leaflets also popped up in other female councillors' wards.

Stretching from the Danforth to the waterfront, Ward 30 is a historically left-wing district – it was former federal NDP leader Jack Layton's ward when he was a city councillor – that includes Greektown, East Chinatown and Little India as well as neighbourhoods that have undergone rapid gentrification, such as Leslieville.

Both Ms. Fletcher and Ms. Farrow lean strongly left, raising the possibility of a split vote and a victory by the centrist Ms. West.

First elected to council in 2003, Ms. Fletcher argues she's the candidate with the necessary political experience to stickhandle the long list of complex issues affecting residents. A long-time member of the NDP, she also calls herself a Ford fighter, saying she helped hand the mayor some key defeats, such as reversing many of his budget cuts in 2012.

"It's been a really hard four years with Ford," she said in an interview on the rooftop garden of the Bridgepoint rehabilitation centre overlooking part of the ward. "We've seen what a difficult term that was and for really new councillors, they had a hard time finding their footing."

Ms. Fletcher's vision for the future rests on pushing ahead files she's been involved with over the years: from waterfront redevelopment and transit expansion to creating more film jobs and supporting neighbourhood initiatives.

Asked about her chief opponents, Ms. Fletcher questions their involvement in the ward. "There's ample opportunity for everybody to have shown their chops here over the last very turbulent four years," the 62-year-old says pointedly. (In all, six people are running for councillor in Toronto-Danforth.)

For her part, Ms. West, who almost managed to topple Ms. Fletcher after entering the 2010 campaign less than three months before voting day, says she's spent the past four years in "constant dialogue" with residents but that her involvement in local issues has been "from a distance."

Painting herself as an Every Mom candidate, Ms. West describes herself as "non-partisan" and "pretty middle of the road." If elected, she wants to deal with congestion, including adding bike lanes, and helping small businesses.

Ms. West received Mayor Ford's support in 2010, although she says she has never met him. "I know he doesn't like [Ms. Fletcher], so he wants someone to beat her. I guess he thinks I'm the person who can do it," the 50-year-old said in an interview at Prohibition Gastrohouse, a local bar.

Ms. West, who is on a leave of absence from her current job co-hosting a Hamilton current affairs show, says she's heard widespread dissatisfaction with Ms. Fletcher, including complaints from residents that "she'll help some people and not others" based on whether they share her political views.

Sitting in her backyard not far from East Chinatown, Ms. Farrow also criticizes Ms. Fletcher for what she says are her "old" ideological tactics. While their social values are similar, Ms. Farrow, who calls herself a "lifelong strategic voter," says she favours "a much more local, empowered, grassroots 2.0 approach."

Ms. Farrow says she's not worried about vote-splitting, saying her real concern was that if she hadn't entered the race, voters seeking a new direction would have had to settle for Ms. West, who she says "doesn't have track record and experience."

"I think Toronto-Danforth is struggling mightily to stay progressive and yet get change," says the 53-year-old.

Ms. Farrow knocks her opponents for living outside the riding. Ms. Fletcher says she's two blocks away, while Ms. West says she lives a block outside.

"I live here. Can I emphasize that enough?" Ms. Farrow said. "It matters a lot to people. They really like someone to live where they represent."

Editor's note: A previous version of this article said Paula Fletcher lives outside her ward because of boundary changes. In fact, ward boundaries have not changed during Ms. Fletcher's 11 years as a city councillor.