"It was an unbelievably generous deal," said Sonnenfeld, a senior associate dean at the Yale School of Management.
So good, in fact, that former SEC Chairman Richard Breeden said the agency likely sees Musk's and the board's decisions to turn down the deal "as another reckless act by Tesla."
"The SEC put a ladder up to the limb [that Musk is] on and tried to give him a graceful way out, showing I think fairly clearly … they are trying to avoid worse damage to the company," Breeden said in the same "Squawk Alley" interview as Sonnenfeld. "But they can't stand by … and have a recklessly false — at a minimum — tweet go into the marketplace."
Breeden said Tesla's actions don't necessarily rule out the possibility of another settlement, but it likely won't be the same deal.
"Every day that goes by, Musk makes it more difficult for them to leave him as CEO. The first deal would have left that and that's going to get harder," he said.
Jason Calacanis, a tech entrepreneur and personal friend of Musk, said he felt the first settlement seemed "reasonable."
"The SEC is in a horrible position here, because they don't want to destroy Tesla," Calacanis said Friday in a separate interview on "Squawk Alley."
"My guess is that they're probably talking right now, and they'll probably continue to talk, and they'll settle this — because they have to. You can't take America's greatest CEO out of the game," he added.