Despite accepting that Bryant's attitude will continue to help the team, the former Lakers coach admits that he wouldn't have given the 35-year-old a $48.5m (£29.5m) two-year contract extension.
"They paid him more than I would have gone for, but what he's given to this organization, what he gives back, he brings a certain sense of, 'We're going to win!'" Jackson told NBA TV. "You got to have a guy on the team that doesn't settle for second.
"That's one of the areas where the value of Kobe, even at this age, is terrific."
Jackson won five NBA titles during his time in charge of the Lakers.