Speaking at the Marketing Society annual conference in London, Dennis reflected back on the racing brand’s relationship with Hamilton and said he had "mixed feelings".
Dennis outlined how he met Hamilton at the age of 12 when he asked for an autograph. At age 13 Dennis signed him to the racing brand, culminating in a career that would see Hamilton become world champion in 2008 before leaving to join rival Mercedes in 2012.
He acted like a "surrogate father" to him, Dennis said, by outlining the boundaries and rules that would enable him to become one of the youngest world champions in history.
Whilst he was celebratory of Hamilton’s successful career, he also said Hamilton had at times gone "off the rails" because he missed out on a "formative" part of his childhood thanks to racing.
Asked whether he saw Lewis Hamilton as a "dirty word" he said "No, of course not".
"I look at him with mixed emotions," he added. "It was an interesting experience for everybody and it wasn’t completely smooth and harmonious, and I don’t approve of everything he does or says."
"But nevertheless great athletes are great because of the sacrifices they have to make. And sometimes sacrifices are in a very formative part of their childhood [so] they don’t always emerge with the all the right social process or behaviour or tendencies that you like.
"If he was at McLaren he wouldn’t be behaving the way he is because he wouldn’t be allowed to... He's shaking off some chains he didn’t want to have."
Dennis also revealed while he doesn't have sleepness nights about McLaren's relatively poor performance in racing currently, he does pause to reflect on it each Monday morning when he wakes up.