Yet, last season, after news first dropped regarding that blockbuster transfer, Wolff was left looking for a replacement for his star man.
That was no easy feat given Hamilton's highly successful 12-season stint with the team, which included winning six drivers' championships and four constructors' titles.
Toto Wolff reveals Max Verstappen fear
18-year-old Italian and Mercedes junior star Kimi Antonelli is the man that has been chosen to replace Hamilton, with big pressure no doubt on his young shoulders as we head into the 2025 season.
Yet, Wolff has also opened up on the pressure that he felt when deciding who would fill the Hamilton void, revealing that he feared repeating a situation involving Verstappen where he missed out on signing the Dutchman prior to his F1 debut.
"It was a curve ball thrown at us, and it still feels weird that he's going to wear Ferrari overalls and drive the red car," Wolff explained on the Armchair Expert with Dax Shepard podcast.
"It's just a bit surreal. But we had this 17-year-old in the pipeline [Antonelli]. I didn't want to miss out on him, like I did with Max [Verstappen] back in the day, I didn't have a car, so that is all falling into place."
Wolff also admits he understood why Hamilton made the decision to leave the Silver Arrows.
"I can kind of get where he's coming from," Wolff added on Hamilton. "Because we weren't successful. Our car was not quick enough.
"Certainly he had a mega offer on the table - every Formula 1 driver wants to drive a Ferrari."