Photograph by Platon for TIME

Carl Icahn is the richest man on Wall Street. He's the most feared corporate raider In the world. He may also be the most entertaining financier on the planet. Having grown up in a family that resembled a darker version of Woody Allen's multigenerational working-class Jewish clan in Radio Days, Icahn is prone to one-liners. His real talent is as a mimic, but when I ask him to do Apple CEO Tim Cook, he declines. "Nah, I can't do Cook. I can only do crazies."

Of course, some people say Cook is crazy to listen to Icahn, who has been trying to persuade him since August to give some of Apple's $147 billion cash hoard back to investors in the form of a massive share buyback. Now Icahn is ratcheting up the pressure: he tells TIME that he filed a precatory proposal with Apple on Nov. 26, three days before the deadline for measures to be voted on at the company's next annual shareholders meeting.

His proposal, which calls for a stock buyback, would not be binding on the company's management, and that's typical for shareholder resolutions. But a buyback would almost certainly push up the price of Apple's stock--and increase the value of Icahn's $2 billion in Apple holdings along with those of all the other Apple investors. Icahn says he doesn't consider his proposal an indictment of Cook, who has been at Apple's helm since Steve Jobs died in 2011. "Tim Cook is doing a good job with the business," Icahn tells TIME. "I think he's good at running the business whether he does what I want or not. But Apple is not a bank."