you think you can win anything if a quarter of your payroll is tied up in Hassan Whiteside? i sure dont. Even though- yes personally- Whiteside isnt as good as deandre or Gobert, etc....but - why would ANY team commit a quarter of their payroll to a center that cant shoot, cant pass, and cant defend the pick and roll?
right away you are already behind the 8 ball and better be perfect with the rest of your cap space.
spend your cap on wings and guys that can play multiple positions, and that can pass, spread the floor, shoot the 3.....
not guys that afraid/too slow to leave the paint to guard a pick and roll.
It depends on how the team is built. With shooters around him, you can absolutely win with Whiteside taking up 25% of the cap. If he has shooters around him, they don't need to worry about his passing. He is definitely athletic enough to defend the pick and roll but, like most centers and most bigs in general, probably hates doing it.
I haven't seen much of Gobert, but Whiteside is better than DeAndre. DeAndre has little to no offense and is a 48% free throw shooter. He is literally a liability late in close games.
Whiteside averages more points, more rebounds, more blocks and is a 60% free throw shooter (still not great, but you can have him on the floor late in close games).