In a sane world, the moment Bloomberg found himself special-ordering custom-sized government-issued drinking glasses for city bureaucrats would have been the moment the fever broke and he realized that his stunningly successful career in finance and politics had ended in ruin and insanity. But no, apparently this is happening. Tomorrow.

Coming next: Size regulations on cup manufacturers?

The Health Department will begin implementing routine inspections to make sure eateries, including sit down restaurants and fast food chains, are not selling sugary beverages in servings larger than 16 ounces.

Those inspectors will have specially ordered measuring cups to help them enforce the new rule, Deputy Health Commissioner Daniel Kass said in an affidavit recently filed as part of the legal challenge to Bloomberg’s anti-big-soda policy…

‘The measuring cups that we will be issuing … will be able to contain 17 fluid ounces,’ Kass said. Inspectors will issue violations when a cup is found to ‘clearly exceed’ 16 ounces ‘when measured in the inspector’s measuring cup,’ he added.

There’s a profitable comedy to be made, probably starring Ben Stiller or Seth Rogen, about the life of an overzealous New York City soft-drink inspector and his mission to clean up the mean streets one fluid ounce at a time. And if you live in the city and you’re thinking about voting with your feet, bad news — the nanny-in-chief’s hoping to take this thing global:

“Everybody across this country should do it,” said Bloomberg, who has already called for the state to bar sugary soda over 16 ounces in stores.

And, he suggested, the crusade might not even stop there.

“In fact, obesity is a problem around the world,” he said. “It’s getting to be as serious if not more so than smoking.”

He said tough moves are necessary because the obesity epidemic will “bankrupt” the healthcare system – and, he suggested, because fat people can’t do their jobs as well as those in better shape.

Here’s the city’s fact sheet (in PDF form) to help restaurants, coffee shops, and convenient stores figure out if they’re bound by the new regulations or not. As was clear from the very beginning, the most arresting thing about Bloomberg’s ban is how haphazard it is. Jacob Sullum at Reason has a nice short dissection of that. Case in point: A 20-ounce black coffee is okay unless it has more than “about as much as three teaspoons” of sugar in it, although if half or more of the coffee is composed of milk (i.e. a latte) then the restaurant can add as much sugar as it likes because the nutritional value of milk somehow magically neutralizes the sugar and makes that concoction healthy-ish. (Sullum notes that a 60-calorie black coffee at Starbucks with four spoonfuls of sugar is banned while a milky 640-calorie large hot chocolate with whipped cream is fine.) But mind you, these restrictions apply only to the restaurant. If you like your coffee black and want a pound of sugar in there, no problem; just add the sugar yourself instead of asking Starbucks to do it behind the counter and you’re golden.

Another example? Okay: Bowling alleys, which you might visit once or twice a year if you’re an average New Yorker, are strictly bound by the city’s new regulations because they serve prepared food. Not bound: The neighborhood 7-11, which isn’t similarly regulated by the health department. That means that the fabled Big Gulp, the scourge of Bloomberg’s dream of shrinking waist sizes by shrinking sugary drinks, is still A-OK. But then, that’s likely by design. This scheme, like so many other liberal regulatory schemes these days, needs to fail in its objective so that more aggressive regulation can be undertaken. It’s win/win for Bloomberg. If there’s a very minor bit of weight loss among New Yorkers, that’s proof that this is “working” but could work better if he clamped down a bit more. If it doesn’t lead to weight loss, that’s proof that he needs to clamp down a lot more to make a dent. The fact that the ban is arbitrary isn’t a bug, it’s a feature.

Update: Apparently there is still such a thing as “too arbitrary.” Wow:

The city is “enjoined and permanently restrained from implementing or enforcing the new regulations,” New York Supreme Court Judge Milton Tingling decided Monday.

The regulations are “fraught with arbitrary and capricious consequences,” the judge wrote. “The simple reading of the rule leads to the earlier acknowledged uneven enforcement even within a particular city block, much less the city as a whole….the loopholes in this rule effectively defeat the state purpose of the rule.”

Looks like Bloomberg will have to move immediately to Plan B: More comprehensive regulation.