How as a young child growing up in the principality, he would take the bus to school up the winding climb to Casino Square, dreaming how he would one day tear up the same roads in a scarlet Ferrari F1 car.
How his late father Herve made every possible sacrifice to get him there but would pass away in 2017 before he ever got to see his son realise his dreams.
How his late friend Jules Bianchi became not just a godfather but a mentor to him, a shining light to follow on the journey from karting together at the Brignoles track, through the Ferrari academy and into F1.
"I realised actually two laps to the end that I was struggling to see out of the tunnel just because I had tears in my eyes," Leclerc admitted. "And I was like, ‘f**k, Charles, you cannot do that now. You still have two laps to finish’.
"I have to say that I was thinking to my dad a lot more. Monaco is the Grand Prix that made me dream of becoming a Formula 1 driver.
"I remember being so young and watching the race with my friends, obviously with my father, that has done absolutely everything for me to get to where I am today, and I feel like I don't only accomplish a dream of mine today, but also one of his."
Leclerc's home race had never been kind to him in the past, which only made his desire to banish those demons even stronger.
The dominant driver in 2017's Formula 2 championship, Leclerc was leading the feature race from pole until his race unravelled through mechanical issues.
His next chance arrived in his first Ferrari F1 season in 2019, but he was eliminated in Q1 due to a wrong decision to stay in the garage for the final minutes, going on to retire from the race due to damage from a mid-pack collision with Nico Hulkenberg.
In 2021 he crashed in qualifying after securing pole, with an undiagnosed driveshaft issue surfacing on the laps to the grid and leaving him unable to start the race at all.
Despite knowing he wouldn't make the start, he walked to the grid to meet with the other drivers and wave to the red-tinged grandstands, as his best opportunity yet to score that elusive maiden win on home soil had once again passed him by.
"In the garage, it was very, very difficult to feel okay," he said at the time. "I guess now I'm getting used to this feeling here, unfortunately. I've never finished a race here. This year I don't start it, starting from pole..."
Determined to make things right, he returned to take pole again the next year, but a strategic blunder by the team demoted him to fourth, with an incensed Leclerc labelling the race a "freaking disaster".
“The win was clearly in our hands: we had the performance, we had everything. I just don’t really understand the call and I need explanations for now. We need to get better," a crestfallen Leclerc fumed.
In 2023 Leclerc and Ferrari were no match for Max Verstappen and Red Bull around the principality, nor were they anywhere else but Singapore.
But under incoming team principal Fred Vasseur, Ferrari did get better. And steeled by the scars of those near-misses, all the pieces of the puzzle finally fell into place this time around.
Armed with a sharper axe in the form of Ferrari's much-improved SF-24, Leclerc backed up a commanding pole on Saturday with a faultless drive on Sunday, even if the deliberately sluggish pace to protect the tyres made it tough to get into a rhythm.
As he weaved his Ferrari across the finish, years of frustration poured out like lava as he shrieked over the radio, before falling into the arms of his crew, Vasseur, and a choked-up Prince Albert II of Monaco, who for the first time witnessed one of his own take the top step of Monaco's unique podium.
"I think the fact that twice I've been starting in pole position and couldn’t quite make it, makes it even better in a way," said Leclerc, dispelling any notion of a Monaco curse playing on his mind.
"I never believed in the curse. However, it always felt very difficult in the two occasions I had to win here. One, I couldn't even start the race. The second one, we didn't make the right choice. So it was very, very frustrating to lose those wins.
"The thing is that as a driver you never really know when will be the next opportunity to win and especially when it's your home race and it's Monaco, that is such a difficult track and such a difficult weekend to master and to do everything perfectly."
While he admitted to feeling "tension" before the race, Leclerc did everything he could to keep the pressure off. Being able to sleep in his own apartment, as most F1 drivers are able to do over the Monaco weekend, was a helpful perk. As was a slightly unorthodox last supper.
"I ate like crazy [Saturday] night," he revealed. "I actually got home too late and I couldn't cook, so I ordered my favourite pizza, which is not the best preparation to race normally, but I was like, ‘OK, maybe mentally it will help me to take the pressure off a little bit’. And I slept really well.
"I knew how it felt the last two times I was in this position. I obviously really wanted to get that victory today, so there was a bit of tension. But as soon as I put the helmet on and as soon as I get into the car, I don't feel anything anymore."
And still, it was impossible to keep all emotions at bay until the end of the race, which he said last happened to him at the 2017 Baku F2 race that took place just days after losing his father, Herve.
"Obviously, everything was still very fresh for me, so it was difficult to manage mentally," he recalled.
"However, it's probably the first time in my career that it happened again while driving, where you've got these flashbacks of all these moments that we have spent together, all the sacrifices that he has done for me to get to where I am."
Yet under the most difficult circumstances, then 19-year-old Leclerc produced a flawless drive to win that Baku F2 race, showing inner steel to match his natural turn of speed.
If that most devastating of losses couldn't derail him then, then there was no way he was going to let his lifelong dream slip through his fingers this time either.
Following years of loss and heartbreak, Leclerc finally found redemption on the streets he roamed as a child.
