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Send him spam? Nah. You can do more damage by doing the exact opposite.
Does the guy run a website? Use harvester software to grab a bunch of e-mail addresses, open a Hotmail account, and make up a spam message advertising his site and anything he sells on it.
Next, report it to SpamCop, SPEWS, SpamHaus, etc (plus other people surely will as well). They are a bunch of fanatical assholes who will likely overreact and block his entire upstream provider from sending e-mail to people who use those blacklists. They'll drop his account in a heartbeat in order to get un-blacklisted, and he'll be down and scrambling to find a new host. That'll likely cost him more than $500.
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