Because not even Apple can know at which prices its shares will trade in the coming years, Milano thinks Apple's $10 billion buyback is misguided. Instead, he called for a special one-time dividend in lieu of buybacks. That could be a $53.60 dividend per share if Apple paid out just half of its $98 billion cash hoard to shareholders. (Remember, Apple recorded $16 billion in free cash flow in the first quarter, so the cash coffers are still growing.)
Most importantly, a one-time dividend would eliminate the risk of paying too much for shares, Milano argues. It would also reward current shareholders without exposing them to the stock market's vicissitudes.
"If I were them, I would have taken the price element out of it completely," says Milano. "Buybacks are a little tricky—they only make sense if share price goes up. But you have no idea if it will beforehand."
Apple is an extraordinary company. But it went with convention on buybacks, leaving shareholders to suffer if its plan doesn't pay off.