The 2008-09 Magic team was pretty good. Dwight was just coming into his prime, but that team had Lewis and Turk very much in their primes as were Pietrus and Nelson. It also had some nice young players in Lee, Redick, and Gortat and some cagey veterans like Rafer Alston, Tony Battie, and Anthony Johnson.
What really hurt them was Nelson barely played in the post season. I'm not sure they overcome the Lakers with him, but they certainly would have had a much better shot with a healthy Jameer.
From that point forward, Orlando started making stupid moves based around Howard. It is actually pretty similar to what the Cavs did with Lebron.