Charles throws a blanket statement without consideration to the different cir stances of each team.
I don't think it's the right philosophy for a team and franchise that say had been through a decade of lottery picks with no playoffs at all. If they finally get to the playoffs even as a 6, 7, or 8 seed, at least they can get some more fan support and excitement and get a piece of the playoff revenue. And after 10 or so years of not going to the playoffs, I think a team like that would appreciate going to the playoffs for a number of years before trying to sell off their good players for draft picks and cap space.
I think where what Charles says might apply is a team like Phoenix where the stars are older (in the mid 30s) and they've had quite a bit of playoff success over the years and the only thing that would really make a huge difference in fan support is actually getting to the NBA Finals and winning a le. So in the case of guys like Steve Nash and Grant Hill, I would agree with Charles that Phoenix at this point would have been better served to trade them for draft picks and cap space.
It's not the same thing with a team like Portland where they just started to get some success and their stars are still young. The window of opportunity (injuries noted) is wider than for stars like Nash and Hill in Phoenix. So while there are instances where I think Charles would be right, there are also teams that I don't think what he says really applies all that well.