Give An American A Privilege Long Enough, They'll Think It's A Right
The crux of the matter seems to be Gilmore's objection to the Transportation Security Administration's directive that airlines must either ask for identification of passengers, or subject them to further screening. To quote the judgement:
Gilmore asserts that because the Government refuses to disclose the content of the identification policy, it is vague and uncertain and therefore violated his right to due process. He also alleges that when he was not allowed
to board the airplanes, Defendants violated his right to travel, right to be free from unreasonable searches and seizures, right to freely associate, and right to petition the government for redress of grievances.
While I agree that a government should not keep relevant parts of its security procedures from its citizenry, he ought to be glad I'm not the judge hearing his appeal, since I find his argument to be spurious on several grounds. First of all, he does not have a "right to travel" in the broadest possible sense. He has the right not to be asked for identification while crossing state borders while inside the United States, owing to border transparency in that jurisdiction. That doesn't mean he can just get on an aircraft without telling anyone who he is, or otherwise following the rules.
As to his charge of "unreasonable searches and seizures," while I do think that some of the current restrictions in place in the commercial airline industry are ridiculous, I also don't think that a security screening constitutes an "unreasonable" search, since there are many other reasons for a security screening than the obvious one at the top of everyone's mind, which is (of course) to prevent bomb-wielding maniacs from boarding aircraft. Unfortunately for people who like to latch on to the airborne terrorist meme, there are plenty of other reasons to have security searches on aircraft besides simply making sure "bad guys" don't get on the plane. One of them is so obvious it might get overlooked: to make sure the passengers don't possess items or engage in behaviours hazardous to the safety and well-being of the other passengers and flight crew. My father is a commercial pilot and has given me chapter and verse on this, detailing exactly why there are restrictions on air travel with everything from pressurised containers to firearms to certain electronics to wearing stiletto heels (if that one seems not immediately obvious, it's because aircraft cabin floors are not designed to take the pressure of even a small woman's weight on a tiny amount of space). The other non-obvious reason for security screenings is to familiarise passengers with the minimal personal safety procedures required for air travel, which is why, when you travel by air, there are all those signs around saying what you can and cannot take aboard an aircraft, and actions you must take in order to clear the screening. Viewed from that perspective, the formality of a security procedure -- while invasive -- hardly seems unreasonable in the legal sense.
Similarly, I think, contrary to his claim, that the governmental and airline requirement to either show ID or submit to an extra search hardly impinges on his right to free association, or not sufficiently so to warrant a legal claim, considering the wealth of other available options (especially for someone who literally has wealth, and claims on his website to have "made [a] fortune"), and the extenuating circumstances.
On the other hand, I don't like secret laws. I don't feel governments have much business keeping things from their citizens, especially things that relate to how those citizens are expected to behave in certain circumstances. If there is such a "secret policy," it needs to be non-secret, and available on request to people who want to make informed decisions about their actions.
That said, he ought to be glad I'm not hearing his case, because I can trump most of his arguments with an even more basic (small-l) libertarian argument: private property. If the government had not issued the directive dictating that all passengers must either show identification or undergo an additional security screening, if it were merely an airline policy (as has been the case in other jurisdictions), I would still feel compelled to uphold that policy on the grounds that the aircraft are the airlines' private property, and they have the right to know who's using them. This is not news; it's not even precedent. It's the same established principle that, for instance, allows a campground to set a "no firearms" policy, and then expel anyone who violates it, even if firearms are legal in the surrounding jurisdiction. It's the same principle that allows restaurants to have "No Gang Colours" dress codes.
Going by that argument, Gilmore loses. (It must suck for someone who's obviously a libertarian of a certain stripe to be out-libertarianed by a Canadian quasi-socialist, but there you go.) If private carriers want to keep passenger manifests, they're well within their rights to do so. If Gilmore wants to travel anonymously, as he obviously feels entitled to do (and why do I get the feeling this is more of a case of "rich guy who doesn't feel like he has to play by the rules" than an actual threat to freedom?), he's more than welcome to travel autonomously -- he can drive, walk, bike, or ride a horse. If he still wants to travel anonymously and have someone else provide him with his transportation service, he can take public transit. He can also stay home instead, and use his technological savvy to make travelling redundant -- teleconferencing is getting easy and cheap these days. However, in the case of air travel, at least, the rules exist for a purpose, so if he's unwilling to play by the rules, he shouldn't get a free ride.