You can wait a long time, because there are too few computer scientists on the intersection of poetry, linguistic analysis and computer security to make that happen. You would need a good estimate of likely sentences used for input and that requires skills far outside the computing sphere.

A statistical analysis will likely reduce the set of probably letter combinations somewhat, but probably not by more than one or two orders of magnitude. An analysis of word-beginning distribution of letters will gain you more. Taking all that into account, my best gut feeling is that you'll end up somewhere in the area of 10^10 in complexity for an 8-character output. Better than passwords (which I've repeatedly estimated at around 10^7) but still not so great and probably much less than you'd expect.

Also, taking into account psychology and the fact that a fairly small set of phrases is much more popular than all the others combined, and that many users will choose a popular phrase instead of a personal one, you would also end up with the "password"-as-my-password problem in that a lot of accounts would have phrases from a list of maybe 1000 popular ones.

Been there, done the math, and I can confirm that the guy is 100% spot on. According to the slides of my last keynote on the subject, it basically goes like this:

We think the complexity of a password made in accordance to a typical password policy (at least 8 letters, at least 2 of them special characters or numbers, mixed upper and lower case) is on the order of 10^16.

What users actually read is more along the lines of "take a word, maybe abbreviate it, add one number and one of the easy-to-type special characters", giving us a complexity in the order of 10^7.

That's not a small difference. That's 9 orders of magnitude. That's like thinking the population of the USA is around 3000 people. That's how far off we are when we think about complexity of passwords in purely cryptoanalysis terms, without taking user preferences into account.

What this guy did is really great, I wish I had time to do such a proof-of-concept instead of just speaking about it every time I get an opportunity.

Your first comment is close. Yes, a serious attacker has many better ways than cracking your password. In fact, I've given another speech on this a few months ago where I basically said that we should drop brute-force as a threat scenario from our password strength estimations, because any software that even allows a brute-force attack to be run is fundamentally broken and needs to be discarded.

Same for cracking hashes, btw. If your software does not properly salt and hash, it's broken. It's 2015, not 1995.

Your second comment is totally wrong and one of the reasons we have so many bad passwords. We tell normal human beings to use a different password for each of the 200 or so sites that they have an account on, many of which they use once a year. That's idiotic, and users are telling us we're insane by ignoring it.

I use 3 different passwords for 90% of the accounts I have. One for all the various forums, social sites and other crap that is of absolutely no importance to me and if it gets leaked and you use it to log in as me on one of them, you can post comments in my name - omg, the sky is falling. One is for sites that I have some stakes in, like accounts in online games and such, where you could do some damage in the sense of destroying something that took me time to create (delete my GW2 characters, I'd hate you for it, but no real damage has been done). And one I use for sites where you could do some damage that I could probably reverse, but it would take effort and might cause me real-world inconveniences, such as shopping sites where you could order something in my name and I'd have to go and cancel the order or send it back or whatever.
My PayPal and banking accounts have their own passwords, as do my user accounts, database accounts and such. But for 90% or so of accounts, you don't really need a seperate password (and using password managers ties you to them, which is why many people don't do it).

And I'm a security expert giving speeches at conferences about these topics. I'm just not a blind one-trick-pony who knows all about cryptography and nothing about anything else. If you begin to figure in psychology, HCI and other topics as diverse as design and linguistics, a lot of what's wrong with IT security begins to emerge more clearly.

Nonsense. The time of naked chess has finally arrived.

You know, just like the TSA will soon make naked flying mandatory.

Also under suspicion: The intelligence of his opponents in those tournaments, because they apparently didn't notice the most obvious strange behaviour ever.

There are pro life libertarians.

Those ones are socially moderate.

LK

This bit of information came to the public's attention because of a Democrat. Dick Morris spilled the beans when the Clinton's let him get pilloried in the court of public opinion.

Of course you don't care. No one who cares about decency or the rule of law would consider voting for Hillary. It's nothing like picking apart someone's grammar. Hillary Clinton was involved with denying due process and justice to women who were sexually assaulted by her husband.

One?
Minor?
Out of proportion?

Bill Clinton raped Juanita Broaddrick. Bill Clinton sexually assaulted Kathleen Willey. Bill Clinton sexually harassed Paula Jones.

When deposed in Paula Jones's civil case, he committed perjury. He instructed people that if they lied, the investigators would have nothing. He suborned perjury. He committed Obstruction of Justice. These are all felonies that would get you or me incarcerated.

You call it decency for Bill Clinton to grope Kathleen Willey's breast and forcibly put her hand on his penis while her husband's dead body was being recovered?

Joe Biden is a crazy asshole but he's nowhere near Bill Clinton in terms of sleaze.

LK

You must be a socially liberal libertarian. Right?

LK

To use her political connections to deny someone due process or justice is most certainly corruption.

LK

If you didn't know about it before, it was informative to you.

Again, Hillary Clinton orchestrated the character assassination of the women who were sexually assaulted by her husband.

It's not my opinion, it happened.

LK

No. That's pretty much the exact opposite of what happened.

Monica denied that anything happened until she was threatened with perjury charges because of Linda Tripp's recordings.

Please, familiarize yourself with the events before you opine.

LK

Yes, according to Dick Morris.

When the Clinton's left him out to dry, he stopped keeping their secrets.

LK

Who said anything about the intern? That was a series of consensual encounters.

I'm talking about the women that he sexually assaulted.

LK

I don't care about Bill Clinton's consensual sex life.

I'm not talking about Monica.

I'm talking about Kathleen Willey, Paula Jones and Juanita Broaddrick, not to mention the other women who recanted their allegations after Hillary's forces put pressure on them.

She victimized women who were assaulted by her husband.

That's far worse than Bill's hanky-panky with an intern.

LK

By all means, you may vote for whomever you choose but please don't lie about it.

Hillary Clinton is one of the most corrupt politicians who has ever been on the national scene. Her job during her husband's administration was to orchestrate the harassment and character assassination of the women who were sexually assaulted by her husband.

LK