AOL just sold ICQ for at least $100 million less than it paid, cementing the brand's infamous association with the absolute worst deals in internet history. To cut a deal with the internet conglomerate is to invite epic disaster.

It's been an awful morning for AOL. It sold instant-messaging service ICQ to the frighteningly backed Russian firm Digital Sky Technologies for $187 million, well under the purchase price: AOL agreed to buy the company in 1998 for $287 million plus $120 million in potential performance bonuses. So this is potentially a $220 million writedown. It also reported a terrible first quarter, with earnings down 58 percent and revenue off 23 percent.

AOL's bloody ICQ write-off isn't even close to the most horrific deal it's been involved with. Earlier this month, the company said it might have to write down its $850 million 2008 acquisition of social network Beebo—all the way down to zero. Ouch.

Then, of course, there was AOL's epically bad $180 billion merger with Time Warner. It was actually a fantastic deal for AOL shareholders, since it cashed out their inflated stock near the peak of the dot-com bubble. But on balance it was a disaster, failing to meaningfully transform either company or grow the combined stock. The Time Warner executive who orchestrated the transaction, Gerald Levin, this past January apologized for presiding "over the worst deal of the century."

It should be noted that none of these transactions involved the current CEO of AOL, Tim Armstrong, who is having to clean up the company balance sheet as AOL finally spins off from Time Warner. Still, the ICQ writedown provides a third example of an AOL deal gone horribly wrong, and one wonders what sort of acquisition premium Armstrong will have to pay the next time he wants to do a deal, to overcome worries about the Curse of AOL.

[Photo of Levin with AOL co-founder Steve Case from January 2000 via Getty Images]