*I know lawyers aren't free, but he'd be paying a lawyer regardless of the letter's style.
I speculate (at the risk of demonstrating my ignorance) that this letter, at 1 page of background and ~4 pages of analysis, may not actually have taken all that long to prepare, especially for someone with intimate knowledge of DMCA and libel/defamation case-law.
Of course, it's a lot more complicated if he has arranged representation rather than just letter-writing, and the contact telephone at the end perhaps suggests he has, so it's quite possible I'm wrong.
I do take your point that it is good publicity and on a related note, it is an interesting tactic to publicly disclose the legal response. It obviously will feed into the public support that the Oatmeal is receiving.
I'm not taking anything away from the letter itself - it was a good read - it's just that I don't think FJ's letter warranted or indeed deserved such an in-depth response.
Edit: I get that he's a high-profile lawyer and was respected for the work he did with sex.com, but the letter didn't seem like it was all that great. "Punch it into Google" was a phrase he used. Seriously?
In terms of his awareness of the flaws, I would say that they would be apparent to most people with an awareness of the basic facts of the case. Obviously in reality, I have no idea of his awareness but I would be surprised if he wasn't.
Even if this was restated in formal terms the same deficiency you describe would still be applicable.
If the original criticism was that the phrase did not disclose sufficient information to identify the particular circumstances surrounding the search results, then the reality is that even if this information was supplied, it would not assist.
The appearance of a post in search results is not the actionable matter, but rather the underlying cause of such appearance (for example a defamatory post referring to x, which then appears in search result for x).
Here, the alleged issue was the reference to FJ on The Oatmeal's site which was in fact completely legitimate.
Disclosing the specific circumstances surrounding the search would only have served to dilute the point of the letter, which as has been mentioned was intended more as a shakedown (albeit a completely flawed attempt at a shakedown).
I also don't think he fully appreciates the complexity of how the web works. I'm sure through his sex.com case he's pretty familiar with how domain names work and the legal recourse for dealing with those, but he just seems totally out of his depth discussing libel.
As for the "punch it into Google", it's hilariously colloquial at best and ignorant of the way which Google works at worst.
On the language point, considering the nature of the language I use in my letters and agreements I draft, I found his letter to be quite refreshing (at least in terms of the language used rather than its intention!).
I am fairly confident FJ's lawyer is aware of the flaws in his case and although an easy target, he is likely to be aware of relevant case law.
The point is that FJ's lawyer's letter was more akin to a shakedown used to obtain leverage, rather than a legitimate letter before claim detailing the full extent of the accusations present.
I would have responded in a blunt fashion denying their claims and asking them to prove loss to the value of $20,000.