In their primes of course. 3 of my favorite players
Maybe the first point forward and one of the best perimeter defenders of all time. Scottie is one of the few 6 time champions in NBA history and even though he was the second option he was almost as important. Having Pippen allowed the Bulls to start 2 shooting guards and have Pippen run the point. Pippen also was able to guard the other teams best perimeter player sometimes so Jordan didn't get too tired and had energy for offense. Scottie is easily one of the most versatile players ever at atleast 6'7" he could play almost any positions and was one of the best rebounding SF ever. He is in my opinion the second best SF ever and one of the most exciting players to watch. Pippen also had 2 succesful playoff runs as the leader of a team in 1994 with Chicago and 2000 with the Blazers. One of the most underrated players in NBA history.
Grant in his prime was a better scorer and rebounder than Pippen but never the proven clutch player or defender Pippen was. Grant was another one of the new type of small forwards in the 90's who played as point forwards like Scottie Pippen. Grant was one of the most efficient scorers, and the best rebounding small forward ever not named Larry Bird. Like Pippen he could play 4 positions and he was unselfish. The only thing bad about Hill's career in Detroit is his lack of playoff success which really puts him a little below Pippen IMO. If not for injuries Grant could have become a legend. Grant had no problem playing point forward and being the number 1 option while grabbing 9-10 rpg at the small forward position. Unlike Pippen Grant was already an all star his first year.
The fact that everyone was comparing him to Magic Johnson including Magic himself should tell you something. Penny was probably the flashiest of the players but very similar. Not the rebounder the others were but he was just as good of a scorer, a proven clutch player and an even better passer. At 6'6" Penny could play PG, SG or SF and play them all as well as almost anyone in the league. Penny was an efficient scorer who was one of the best at both creating shots for himself and his teammates. For a very short period of time Penny was arguably the best player in the league. I have no doubt if not for injuries he would go down as one of the 10 best point guards ever. Considering his best seasons were probably his first few in the league we never really got to see what he could do.
In his prime it is hard but I have to say Pippen. Pippen was the best defender and while he wasn't the best scorer, passer or rebounder out of the 3 he was very close in all 3. The 6 titles is very impressive and he proved he could lead a team in the playoffs without Jordan in 94' and 00'.
grant hill (1994-2000)
based on their numbers, i assumed that both players declined significantly after the 99-00 season. during that span, grant hill posted better numbers compared to penny.
imo, i'll still go with grant hill, he's like a more polished but less athletic version of lebron. he was the definition of a complete player during that time. with regards to penny, fair or not fair, i'll always look at him as shaq's backup