Kouvalis rejoined the team to lead research and polling. Tory’s campaign says Kinsella, who was running 2014 mayoral candidate Olivia Chow’s campaign war room as a volunteer, is a “volunteer” in Tory’s own war room.

The two strategists are in a position to shape the race as Tory faces an unexpected challenge on the left from former chief planner Jennifer Keesmaat. They help decide which issues become Tory’s policy promises, how to message them, how to play the ground game of turning support into votes and the overall tone of Team Tory.

Heading into the election, Tory — who rarely causes a stir with his public comments and has tried to appear as a calm presence in the years after former mayor Rob Ford’s chaotic term — had high public approval and no big-name challenger necessitating a heavy-hitting campaign. With Doug Ford now premier, Tory had avoided what was expected to be a heated, scrappy redo of the 2014 race.

The former bureaucrat used her campaign launch to signal the gloves are off. She branded the mayor “dithering,” “timid” and “low-energy.” His campaign quickly returned fire, saying she is full of “empty talk.”

What is certain is that, for a bare-knuckle fight, Tory has two very accomplished campaign veterans in Kouvalis and Kinsella. What is less certain to some close to the campaign, who spoke to the Star on condition of anonymity, is if the benefits outweigh the risks both men bring to the team.

Kouvalis, who was Rob Ford’s chief of staff after pushing him to victory in 2010 with rhetoric about a “gravy train” at city hall, was hailed in 2014 as Tory’s “Ford whisperer” when he joined the campaign that saw Tory best Doug Ford for mayor. He has remained loyal and in constant communication with Tory since, several sources say.

“I don’t support many of Nick’s clients and I don’t approve of all his methods, but he’s a brilliant strategist,” says Willowdale Councillor John Filion, a suburban progressive who fought Tory on issues including a plan to remake north Yonge St. Filion is seeking re-election in the 25-ward race.

“You’re always better off having Nick on your team, he’s one of the smartest people I’ve met,” he says. “He is an analytical thinker with a good understanding of data and he has remarkable street smarts. Usually you don’t have those in the same person. He’s also great at predicting people’s behaviour.”

Kouvalis has embarrassed Tory in the past. In 2016, while under fire for running a federal leadership campaign for Kellie Leitch focusing on immigrants and “anti-Canadian values,” Tory said he would welcome Kouvalis, “one of the smartest people I know,” to his 2018 team.

The mayor faced more questions after Kouvalis on Twitter called a constitutional expert critical of Leitch’s policies a “cuck,” short for cuckold. The slur is often used by white nationalists and other alt-right groups. Kouvalis later apologized and resigned from Leitch’s campaign.

Also in 2016 Kouvalis pleaded guilty to drunk driving after crashing his Lexus into a concrete culvert in Tecumseh, near his Windsor-area home. Fined and temporarily banned from driving, he said in a series of tweets he had struggled with alcoholism since 2011.

Last September the strategist was charged with breaking and entering after police said they found him and an aspiring politician drinking in a closed Kelsey’s restaurant in Burlington. Charges were dropped earlier this year in exchange for their guilty pleas to non-criminal trespassing.

Kouvalis remains a combative presence on Twitter, lashing out at ambiguous enemies in a string of late-night tweets.

In a now-deleted Aug. 6 tweet, Kouvalis wrote: “1 day, I will write a book: the left-center-right, & how they all f—– everyone & perhaps I will write some ‘colour’ about the journalist on the way …”my favourites (who were pros along the way & the a–wipes too) {Remember that I won, a lot} don’t ever forget, how I won that” (sic).

In another, still posted, he wrote “Shame on you, the left, for what you are trying to do. You all know the truth, but you’re playing your game. Shane on you!” He asked left-leaning councillor Paula Fletcher “Will you let them assinate me?” (sic).

Tory has said he has supported Kouvalis through his struggles because that’s “what you do with people that are your friends.”

A source familiar with the mayor’s office and its relationship with Kouvalis said Tory “needs him. It’s that simple.”

“People point out Leitch (losing) but he has helped many people win. On winning, Kouvalis’ track record is better than Tory’s and the mayor knows that. Also, Nick’s a hired gun and if he doesn’t work for you he might work against you,” the source said.

Kouvalis declined to answer the Star’s questions, writing in an email that his company, Campaign Research, “does not disclose, discuss, confirm, or deny the existence of any matter relating to who its clients are, or may be,” unless required to by law or directed to by the client.

Keerthana Kamalavasan, a spokesperson for Tory’s campaign, said in an email: “Toronto residents know Mayor Tory’s values and what he stands for. He has been a champion for an open, inclusive city that embraces people from all cultures and walks of life.”

More surprising to Tory confidantes than his attachment to conservative Kouvalis is the welcome mat for Kinsella, a tart-tongued Liberal who has also quit a campaign over a tweet and who took Kouvalis to court when they were in enemy camps.

Kinsella launched a $100,000 defamation suit over a 2014 tweet in which Kouvalis lauded the Chow campaign for “dumping” Kinsella. Kinsella said he left of his own accord after calling Tory’s SmartTrack plan a “Segregationist Track” that avoided low-income neighbourhoods.

Kinsella later deleted the “Segregationist” tweet and apologized to Tory. Kouvalis, Kinsella and a lawyer for Kinsella did not respond to the Star’s questions about the status of the lawsuit.

When Chow reacted to the “segregationist” tweet by downplaying Kinsella’s role on her campaign as a volunteer, Tory criticized her response as inadequate and failing to take responsibility.

“I would like some accountability from her and to say that this was a senior operative in her campaign . . . and that she finds those kinds of comments reprehensible in the context of politics and utterly without any foundation at all when it comes to me personally,” Tory said at the time, as quoted in the Toronto Sun.

Kinsella is a well-known strategist and former principal at high-stakes crisis communications firm Navigator who wrote the book The War Room. He appears to relish a fight, on Aug. 3 calling a journalist a “bitter little s—head” on Twitter and vowing to “kick his ass” in a debate.

Kinsella ran the war room for the federal Liberals during the 1993 election and Tory was the Conservative’s campaign chair. The Conservatives released attack ads highlighting then-Liberal candidate Jean Chrétien’s facial deformity, a move Tory defended at the time.

Kinsella, who a decade later helped Tory during his failed 2003 mayoral bid, posted on his personal website Aug. 1 he would volunteer for Tory “if he wants me,” listing several reasons why, including that he “believes in redemption.”

“When I made a stupid, thoughtless, unfunny, idiotic tweet during 2014’s race, John accepted my apology — and we resumed our friendship,” Kinsella wrote, apparently referring to the “Segregationist Track” tweet that prompted him to leave Chow’s team.

Kouvalis and Kinsella appear to have publicly mended fences.

Lisa Kinsella, Warren’s wife and partner in Daisy Group consultants, said in an email: “As Warren’s partner, I can tell you that John Tory is a great family friend, and we are delighted to support someone who has done so much for Toronto. In addition, Warren and Nick have become close friends and John Tory is the one who brought them together. John has the ability to bring people together, not separate them.”

The source with knowledge of Tory’s campaign said Kinsella’s welcome with the mayor appears to be linked to Tory’s fear of losing.

“How scared is he of Montreal happening in Toronto?” the source said early in the campaign, which started in May, referring to Valerie Plante’s surprise 2017 defeat of Montreal mayor and former federal cabinet minister Denis Coderre.

“Tory’s terrified of being a one-term mayor.”

With about three weeks until the vote, however, opinion polls suggest Tory still holds a commanding lead over Keesmaat.

Asked to respond, Kamalavasan, the Tory campaign spokesperson, said: “Warren Kinsella is a volunteer helping out in the campaign war room” and noted his previous role on the 2003 campaign.

“Staff and volunteers aren’t the issue in this election. The candidates, their records and their plans are.”

Asked about Tory using Kouvalis and Kinsella, Keesmaat said: “Toronto is at its best when we’re all working together towards the same goal, and I think we’re all disappointed when discourse becomes too venomous.”

“It’s up to John Tory to decide what kind of campaign he wants to run and who he wants to run it, and the people of Toronto will assess him on that choice.”

Jennifer Pagliaro is a Toronto-based reporter covering city politics. Follow her on Twitter: @jpags

David Rider is the Star’s City Hall bureau chief and a reporter covering Toronto politics. Follow him on Twitter: @dmrider