I'm surprized he paid Jill.
At one point and time, I actually paid a retainer fee for an attorney to send cease and desists when I saw my artwork elsewhere that wasn't paid for. It was worth it a decade ago, paid $500 to have the attorney, and $95 every time I sent a cease and desist .. sadly, I don't have need of it because when I do design work, I make them sign my terms when they put a deposit for work in ... it states that I will charge them my usage fee if they use my design work elsewhere without paying the usage fee for the rights to the work or an exclusive rights fee which it is then free and clear from that point on. It also states how fast I will let them pay without sending it to collections if it was used without authorization. when they ask what I mean, I tell them, set the expectations that they aren't paying for the design work for them to take so it's entirely mine until that time but we can discuss options if they want the art later or want the art right when the job is finished. I sell more logos doing it this way, get less calls for art, and if they do go somewhere else for graphics ... it's 95% chance with the cheapest person there is in town and I don't give two farts after that. Now, I don't really do proofs they can easily shop around, all my conditions on art are on the proof with the image heavily watermarked (if e-mailed) and at low res. Even then it's rare for me to do spec work without at least an art deposit (which they can apply to a full job) so most of my art problems have disappeared. I will occasionally do some freelance bidding, but even then I never do spec work, just give a portfolio page showing what I can do.
Mind you 90% of what I said is invalid if someone pays for all the artwork right out ... I give them a flash drive with the eps and ai files converted to illustrator 8 (if vector based and not 3d based) all raster exports and color variants. They also get a letter stating a "Secession of Intellectual Property" from me if they buy exclusive rights (such as logos, illustrations, etc)
I should also note, I don't make people pay for artwork from a 2 minute layout of a coroplast sign, those people just want a simple 200px jpg and at most, I tell them to bring me a fiver to cover my time hitting export and off it goes. I also don't have the terms on such silly endevors only real design jobs.