The 'will it be this year?' question, not asked in 2020 when there was no race due to the COVID-19 pandemic, has grown more persistent.
Leclerc has yet to stand on his home podium in five attempts, four with Ferrari, but he can end that 'jinx' on Sunday.
"Monaco is very special for me. True that it hasn't been the most successful race for me until now," he said after finishing third in last weekend's Emilia Romagna Grand Prix at Imola.
"However, the pace was always there and that gives me the confidence that it will be the case this year too. However, Monaco is so specific that we need to start a little bit from a blank page.
"Free practice is super, super important to build the pace little by little. But I'm confident we'll be strong."
The twisting, metal-fenced streets have certainly not been kind to the kid who grew up watching the red Ferraris and travelling the track by bus on his way to school, dreaming of one day racing there.
In 2021 he secured pole but could not start due to a driveshaft failure.
In 2022 he was fastest again in qualifying but finished only fourth. He also crashed a 1974 ex-Niki Lauda Ferrari when he drove it for a demonstration run at that year's Historic Monaco Grand Prix.
Last year Leclerc ended up sixth. In 2019 he failed to score.
This time he arrives with four podiums from seven races and second in the standings dominated as ever by Red Bull's Max Verstappen.
Absorbing battles
Red Bull's triple world champion won last year and his increasingly absorbing battle with McLaren's Lando Norris is the talk of the sport.
Norris beat the Red Bull in Miami for his first F1 win and finished second in the races either side of that in China and Imola.
Verstappen has meanwhile won five out of seven and started all on pole position, a run of eight in a row including last season, equalling two Formula One records in the process. No driver has ever taken nine successive poles.
"You've got two guys at the top of their game going at it like (heavyweight champions) Tyson Fury and Oleksandr Usyk," commented Red Bull team boss Christian Horner after Norris finished 0.7 of a second behind Verstappen at the last race.
"It was literally sector for sector, fantastic racing at the end of the race... You can see the cars are converging. The latest upgrades, they are all becoming very similar."
McLaren will be running a car with a special Ayrton Senna livery, a tribute to their late triple champion who died 30 years ago at Imola and who remains the most successful driver around Monaco.
"It's about time someone put him (Verstappen) under pressure and he felt a bit of nerves again, because I'm sure he hasn't felt it for a while," Norris said on Wednesday.
"I don't want to be overconfident, that's never been me, but we want to come into races now and be confident in racing against the Red Bull, racing against Ferrari, because we are in the mix with them."
Mercedes' Lewis Hamilton will also be one to watch, given the seven times world champion's past success, while RB's Daniel Ricciardo is another previous winner.
So too is Verstappen's teammate Sergio Perez and Aston Martin's Fernando Alonso.
