Jerry Levin should have cashed in his AOL Time Warner (AOL) options when he had a chance a few months ago.
His key colleagues from AOL did - including Steve Case - and they walked away with hundreds of millions in cash while Levin was left with a nest egg of 10.3 million options that are now worthless.
Many others on the Time Warner side held off - and their losses are now causing new tensions with their counterparts at AOL who were quick to pull the options trigger.
For Time Warner execs, the losses are just another indication of how badly they and their shareholders were burned when they sold their company to AOL for 45 percent of the merged entity.
Levin, outgoing CEO of the merged company, saw his options go up in smoke after the crash of the company's stock. Levin's options had a potential value as high as $325 million last year.
His stock also was slammed, dropping from a value of $103.4 million last year to just $53.8 million today.
His $400,000 annual pension, however, is unscathed by the 33 percent drop in the stock.
Soon after AOL merged with Time Warner, managements of both companies got to redeem all their options at the closing. Many in the AOL crew cashed in their options steadily over in following months, while Levin and other Time Warner executives held onto theirs.
"That was the AOL way - people sold regularly," said one company insider.
"That's what they do and that's what they've done in general in the history of AOL."
Some Time Warner executives were rankled by AOL execs' quick dumping of their options. "They're all worthless now," grumbled one veteran.
Case, the former chairman of AOL and current chairman of the merged company, redeemed $127.3 million of his options in recent months before the bottom fell out of the company's stock, according to regulatory filings.
Another honcho from the AOL side of the merger - AOL's General Counsel Ken Novack - also cashed in $31.5 million of his options.
Case's right-hand man, Bob Pittman, also climbed on the redeem-and-run bandwagon by cashing in $61.6 million of his options.
Levin didn't redeem any options. But his No. 2, Dick Parsons, the former president of Time Warner and the incoming CEO of AOL Time Warner, didn't hesitate. Parsons gained $26.9 million cashing in his options.
According to regulatory filings, the options still held by key executives include: Case, 18.3 million; Levin 10.3 million; Pittman, 14.9 million; and Parsons 3.6 million.
Case used some of his cash out gains to buy back 1 million AOL Time Warner shares when the price was at $24 in February. Case owns about 12.4 million shares outright.
Levin isn't broke by any means. He got a $10 million bonus paid in cash instead of options in 2000. He also got his $1 million annual consulting contact extended for two years after he steps down next month.
But his fortune has dramatically shrunk.
Meanwhile, a new company rule forbids all executives from getting cash bonuses. All will be paid in options, and options are redeemable only when the stock price is 50 percent above a predetermined level.
It's going to be tough to make any money from the options. An AOL spokesperson said that half of the most recent batch of options granted to executives were based on a $48.96 price, with another one-quarter redeemable at $61.20 and the remaining at $73.44.
AOL Time Warner stock closed Friday at $20.93, down 28 cents.