Hamilton heads into Sunday's Monaco Grand Prix six points adrift of title rival Sebastian Vettel in his bid to become the first Briton to win four championships.
The 32-year-old is now in his fifth campaign with Mercedes – a relationship which has yielded an incredible 34 victories and two championships – but one that has not passed without controversy.
Wolff, however, is hopeful that Hamilton, who is in the second of a three-season deal, will see out his time in the sport with the Silver Arrows.
Lewis Hamilton is in his fifth campaign at Mercedes
Toto Wolff is optimistic Lewis Hamilton will remain at Mercedes for the rest of his career
“If you would have asked me the same question one year ago, I would not have been very optimistic, but now it is different,” said Wolff.
“I have the feeling that it can’t be much better in a different place. For him and for us.
“This is very strong now, and I am not speaking only about on-track performance because there are going to be difficult moments, but I am speaking about the relationship.
F1 2017 Drivers' World Championship standings Mon, May 15, 2017
Express Sport runs through the current F1 Drivers' World Championship standings
Play slideshow GETTY 1 of 22
Who is top of the F1 Drivers' World Championship after Round 5?
“After five years, this relationship has become so strong in a way that it wasn’t last season.
Get Quotes on Home Insurance
"For Lewis it will be important to see whether we are competitive or not, but at the moment there is such a solid basis that I can imagine it going on forever.”
Spaniard Fernando Alonso, who missing the Monaco Grand Prix, will fulfil a liftetime’s ambition when he races in the Indy 500 tomorrow.