In his 23 IndyCar starts across four seasons with as many different teams, Luca Filippi showed flashes of the pace that had taken him to six victories in GP2 between 2006 and 2012. That was never more clearly on display than at his favorite circuit in Toronto, where the Italian scored his only series podium in 2015. He finished runner-up to CFH Racing team-mate Joseph Newgarden in a memorable 1-2 for the underdog outfit, but that only tells part of the story of a race he feels unlucky not to have won.

Filippi is certainly well-qualified to pass judgment on street tracks given the various venues he’s competed at in an international career that featured trips to Monaco, Valencia and Singapore while on the Formula 1 undercard. The 38-year-old raced on the famously bumpy streets of Baltimore, as well as at Houston, St. Petersburg and Long Beach in IndyCar, while a season of Formula E in 2017-18 took on trips to Hong Kong, Marrakech, Santiago , Punta del Este, Rome, Paris, Zurich and New York. Then there’s the inner-city Copenhagen track and classic Pau circuit he sampled during his tenure in the FIA ETCR electric tin-top series.

Filippi acknowledges that Spa is “above them all” in a ranking of the best driving challenges and reckons “anyone who has driven” there would agree that “there is nothing else as good as that.” Similar tracks that evolved out of public roads he believes “have generally a better feel for the driver because it’s more of a natural elevation change rather than being artificially designed on a field.” That’s certainly not an accusation that can be levied at the 1,786-mile track that weaves through the lakeside streets of Canada’s largest city.

“Toronto you literally race the streets,” he says. “When you have street courses where you really follow the streets, they are the best. And Toronto is really nice because it is also near the coast of [Lake] Ontario, the configuration of the road and of the corners is not the typical American configuration which is 90-degrees all the time, so it has more of a natural flow.

“You have proper kerbs, some higher than others, and some roughness and bumpiness that you find in [North] American circuits, but a decent amount which is still fun to drive. Also you have a little bit of elevation change like Turn 1, it’s braking a little bit downhill and then it’s off-camber. At the end of the back straight which is quite long, it goes up again, so this is quite nice in a street course.

“When I arrived there it was really difficult to start with because it’s a really complicated circuit but then I raced the rhythm and when it got to qualifying time I was up there. It’s one of those places that it clicked.

Photo by: Phillip Abbott / Motorsport Images

Filippi made his circuit debut in 2014 with RLL and enjoyed the way he could attack the kerbs

“I had a couple of corners where I could find a very good feeling and a rhythm and it was quite easy for me to be consistently fast, where sometimes you have to do more of a mental effort to really find the limit in every single corner , especially in a street course. In Toronto, I was up there from the beginning.”

Filippi had made his series debut in 2013 with Bryan Herta Autosport, managing a single top 10 finish at Houston from his four outings, and for 2014 agreed to a two-round deal in the second Rahal Letterman Lanigan Racing car for Houston and Toronto. A month after his strong showing in Houston’s “big basically parking lot”, where he qualified fourth but was one of many to crash in the race on a damp and slippery track on cold tires following a restart, Filippi again comes out firing in Toronto.

The first of two races was postponed by a day amid rain so heavy that Arie Luydenyk lost control of the safety car and aquaplaned into the Turn 3 runoff, while front row starter Will Power also floated into the wall at the final turn. “I’ve never seen anything like that!” says Filippi.

“For the first time I could be on the right foot from practice one, because I had all the references I needed. I knew what to expect, and so also from a goal-setting point of view I really started with high expectations” Luca Filippi on Toronto 2015

Power’s repaired car was reset to the back of the grid for the belated start, which lifted Filippi to sixth, and after fencing off Justin Wilson at the start he scented the fifth place held by Simon Pagenaud. Filippi stuck a wheel inside through the fast Turn 4 left-hand sweeper, but contact turned the Frenchman around and caused a track blockage that resulted in a red flag.

The longer-term effects were more severe for Filippi than Pagenaud, who charged back to finish second. Damage to the RLL car’s front wing “looked nothing but then lap by lap, the downforce was creating the crack to get bigger and bigger and then it failed”. Struggling with worsening understeer, he tagged the wall with both right-side tires at the final corner.

The treacherous conditions returned later in the day and turned race two upside down. A small mistake in sliding straight on at the Turn 8 right-hander cost Filippi valuable track position and prompted a gamble to keep his aging wet tires when most had followed Mike Conway in switching back to slicks under a late caution.

He was well inside the top 10 when he was caught up in a melee at Turn 3 that resulted in a puncture and an eventual 16th place finish, but Filippi acknowledges that his performances in “the only two race weekends I had [for Rahal] “It is definitely what made people interested in me and generated my opportunity with Carpenter the year after.”

“I did what I was there to show, which was that I was competitive, I was able to compete with the best of IndyCar and that I was a guy ready to race,” he says.

Photo by: Michael L. Levitt

Although he didn’t get a result in 2014, Filippi believes his promising showing was key in earning a seat at CFH Racing for the following year

Filippi took the seat vacated for 2015 by Conway, who had joined Toyota’s World Endurance Championship assault, as CFH Racing was born out of the merger between Ed Carpenter Racing and the Sarah Fisher Hartman Racing squad Newgarden had driven since 2012.

Sharing the second CFH entry with Carpenter, Filippi was assigned the 10 road-and-street course rounds, while oval specialist Carpenter focused on the remaining six venues. Toronto was the first he’d visited before, and it was understandably his strongest showing him as Filippi lined up sixth, five spots ahead of full-timer Newgarden.

“I arrived there very motivated,” Filippi remembers. “Everywhere else, it was my first time. The only two [I knew] were Toronto and Mid-Ohio [rounds eight and nine on his schedule]. So for the first time I could be on the right foot from practice one, because I had all the references I needed. “I knew what to expect, and so also from a goal-setting point of view I really started with high expectations and definitely was really strong all weekend.”

Filippi had gained a spot from Juan Pablo Montoya‘s visit to the Turn 3 escape road and consolidated fifth after switching to slicks, meanwhile Newgarden made little progress. But his race was made by the timing of his second pitstop on lap 28, just before caution flags waved for James Jakes plowing into the tire barrier at Turn 5. Newgarden caught up to the rear of the snake behind the safety car, then vaulted to the front when the pits opened and the vast majority came in.

“He was just trying to get out of sequence,” says Filippi, who puts Newgarden’s subsequent success firmly at the door of race strategist Andy O’Gara. “Then he just came out of the hat of the magician.”

Helio Castroneves stayed out in the lead, hoping to profit from running in clear air, but had little hope of overcoming his deficit to Newgarden – whose cause was helped by having a buffer of two cars between him and the early leaders: Carlos Munozwho had followed Newgarden into the pits, and rookie Rodolfo Gonzalez, who had started last and had nothing to lose attempting to emulate Castroneves in staying out.

Meanwhile Filippi vaulted to the head of the runners on the standard strategy by passing Pagenaud before overcutting Sebastien Bourdais, Power and Scott Dixon following the next round of stops. He had also cleared Munoz by the time the Colombian retired with mechanical dramas.

Gonzalez couldn’t match the pace of Castroneves – who rejoined third – on the offset strategy and before his final stop had been caught by Newgarden and Filippi. With 15 laps to go Filippi got around the outside of his team-mate at Turn 3 but, perhaps thinking of the clash with Pagenaud the year before, he backed out of a move at Turn 4.

Photo by: Jake Galstad / Motorsport Images

A superb drive on his return to the track in 2015 saw Filippi overcut his way to the front of the original leading group

“I would have had the inside for the corner after but at that point, I have already been called on the radio twice in order to be smart,” he remembers. “I knew staying on the throttle I would have kept the line, but it would have been a risk for the other car to crash and I didn’t want that.

“I probably should have done it, but it was definitely not my style. If it was probably someone else, I would have stayed on the throttle, nobody could have ever complained. I just decided to be smart for the team result, thinking that could lead to an extension of the contract, it didn’t happen in the end. “I have some regrets in a way, but it could have been a disaster to crash both cars.”

Filippi returned in 2016 for his fifth and final appearance of a partial season with Dale Coyne Racing‘s minnow outfit. The #19 car that was also raced at various stages in the year by Gabby ChavesR.C. Enerson and Pippa Mann would never qualify higher than 11th all year – Filippi’s Toronto feat matched by Enerson at Watkins Glen – and his race should be viewed in that context.

On what remains his most recent appearance at the pinnacle of US single-seater racing, Filippi was left to rue the timing of a yellow that he felt had warned a potential top-10 run. At the flag Filippi was 14th, one place ahead of team-mate Conor Daly.