When you mention Scottie Pippen, you tend to get a lot of varying opinions. Typically what I hear most is that Scottie Pippen is very overrated and wouldn't have been nearly the player he was had he not been with Michael Jordan his whole career. I tend to take the complete opposite position.
Scottie Pippen is one of the most underrated players ever because he played with Michael Jordan. Some people might say 25 is too high of a spot for Pippen, but honestly I would be more likely to make him higher on the list than I would to put him lower. Obviously Michael Jordan was great, I think he was the best NBA player ever, but he's not winning all those titles without Scottie Pippen.
Scottie was a jack-of-all-trades. He was never a great scorer or great shooter, but he didn't have to be. And that's just a small complaint against a guy that did almost everything else well.
What was it that he did well? For starters, he's one of the best defensive players ever. He was quick enough to guard and disrupt PGs such as Mark Jackson in the 1998 playoffs, his long arms wreaked havoc with offensive players on the wing, and at 6'7'' he was tall enough and quick enough to guard guys down low. He's 5th in the NBA in career steals, nearly had 1000 career blocks, and was on either the 1st or 2nd team All-NBA Defense every year from 1991 to 2000.
But he was far from a defensive specialist. With his unique skills he practically started the concept of a "point forward." With his size and ballhandling skills that added another dimension to whatever offense he was in. He was also a great passer that averaged over 5 assists a game for his career. In 1992 he averaged 21 PPG, 7.7 RPG, and 7.0 APG. Which reminds me, he was a pretty darn good rebounder as well, averaging 6.4 a game for his career but pulling down 7 or 8 a game during his prime.
And this was not all because of Jordan. In 1994 when Jordan retired for the first time, Pippen stepped up his game. He averaged 22 PPG, 8.7 RPG, 5.6 APG, 2.9 SPG, and finished 3rd in the NBA MVP voting. The team didn't do so bad either, winning 55 games on a team whose 2nd and 3rd leading scorers were Horace Grant and BJ Armstrong.
Later in his career as he joined Portland he lost a step or two athletically but still did whatever he could to help the Blazers come within a quarter of going to the Finals.The points when down a little as Pip scaled back shooting, but he kept rebounding, passing, and playing excellent defense.
Those that don't like Scottie will point out how he refused to re-enter the end of a playoff game after not having the final shot drawn up for him... and while I can't defend that action, I'm willing to forgive.
So while some might call Scottie Pippen overrated, I lean the opposite way. He was one of the great all-around players ever... he scored some, played great defense, rebounded, and was unselfish with the ball. He played with the greatest player ever, but that doesn't make him any less of a player.