Yet, last season, after news first dropped regarding his 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 eight constructors' titles.
Wolff reveals Verstappen signing fear
Mercedes junior driver and 18-year-old Kimi Antonelli was chosen to replace Hamilton, with big pressure no doubt on his young shoulders as we head into the 2025 season.
However, Wolff has also opened up on the pressure that he felt when deciding who would replace Hamilton, and that he feared repeating his mistake with 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 admitted that 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."