Kemp for Pippen Trade in 1994

It all depends on what the design was.

In the linked article, there was also mention of a Kendall Gill and Mitch Richmond trade and an attempt to sign Horace Grant at PF.

First, while Kemp was a great player and one of the better PF of his era, Scottie was arguably the best at his position in the game and one of the greats of all-time (in Bill Simmons' Book of Basketball Pippen was 24th all time and Kemp 88th).

Second, after the '93-'94 season, it was very clear that Kendall Gill wasn't a great fit on this roster as his game was about having the ball and slashing to the basket. He needed the ball in his hands and that wasn't going to work. Moving him for Mitch Richmond who was a dynamic scorer who was capable of being a catch and shoot guy made a ton of sense. Particularly with Payton and Pippen on the court, you could then hide Richmond on defense fairly easily. Instead, you held onto Gill, watched his stock drop further, and you ended up getting Hersey Hawkins. I love the Hawk but he wasn't Mitch Richmond.

Third, if you were able to then go out and sign Horace Grant to a deal, you'd solve the PF issue as well as a long-term lingering issue through those Sonics teams of questionable depth. You'd be able to move Det back to the bench and able to play the 3-4 positions and have a very strong 2nd unit - particularly if you also included Ervin Johnson in your starting lineup as that would then push Perkins to the bench. Even if you switched that, when you add Mac10 into the equation, you then had a very deep 8 man rotation with everyone of your bench guys capable of being a starter on a championship caliber club. And that doesn't even include guys like Vincent Askew who were capable of providing solid minutes.

I can understand being cautious about making the deal. I can understand thinking about the implications of the deal and how you made your lineup better to cover a weakness that would be created. But in the long run, that's a club that has significantly better depth and would have had the flexibility to go small against a team like Phoenix (GP, Mitch, Pippen, Det, and Perkins) or big against a team like Houston (GP, Pip, Det, Grant, Perkins/Johnson). It's a team that probably wins a title and quite possibly 2 or 3. You probably take away Houston's 2nd title, you'd nip the Bulls 2nd 3 peat in the bud, and be better positioned to neutralize a Utah team that couldn't keep up with this depth.

In the end, Wally Walker was always a pussy looking for an easy solution. He definitely didn't have any forward thought to how the game could or should be played. He had a massive ego (that was never deserved) and instead of working with his coach to try to build the optimal roster based on a desired way of playing he would dictate to the coach the way he should play.