To be fair, who was going to win in an era with MJ/Pippen, Shaq/Penny, KJ/Barkley ,Stockton/Malone, Clyde/Cassell/Dream, Ewing and Reggie? Robinson was a one man band in the 90s.
To be fair, in the early days of TD, he played against these guys in the finals
1. Knicks with none of those aforementioned stars (Spree, Allan Houston, Camby)
2. Nets with Kidd + a bunch of young guys who were all good but not on the level of the aforementioned guys
3. Pistons with a hall of fame defense and 4 all stars but arguably none on the level of the aforementioned guys
4. LeBroom with a bunch of scrubs
...and even Duncan lost against the better teams of his era (Shaq/Kobe Lakers, Dirk Mavs, Kobe/Pau Lakers etc)