This doesn't sound like blackmail, or anything. Apparently, JWOWW's ex, Tom Lippolis, sued JWOWW after receiving a letter from her lawyers saying that the first payment for his managing services was on the way. That may seem like proof that Tom is actually owed the $350,000 JWOWW allegedly stiffed him. However, along with that letter from JWOWW's attorneys came a plea for Tom to give back the photos of JWOWW in his possession "that may be derogatory to her image and in violation of her contract with MTV." Uh, translation: nudie pics.
Friends of JWOWW have confirmed that Tom is, in fact, in possession of nude photos of the Jersey Shore babe. It sounds like Lippolis wants JWOWW to hand over the money, and he'll hand over the photos.
Perhaps in the future, JWOWW, you may want to be more discreet with which greedy boyfriends you let keep naked pictures of you.