I'm not reading this entire thread, but I'll respond to the OP and the most recent posts.
Has anyone brought up Karl Polanyi (of The Great Transformation fame)? He writes that socialism is the subordination of the economy to democratic desires. It's a fairly broad definition, and I think that even John Maynard Keynes (who once wrote to Hayek to profess his ideological kinship with The Road to Serfdom) would fall under its umbrella. Nonetheless, I think he is particularly instructive here.
Polanyi is writing in response to a culture of laissez-faire that came to dominate in the latter half of the 19th century and the beginnings of the 20th. He criticises the goal of laissez-faire as impossible, and he writes that all attempts to implement it are doomed to fail, with harmful consequences for the people. He has lots of interesting stuff here about fictitious commodities, but I'll cut to the good stuff. He says that a true laissez-faire market society subordinates the people to the interests of property. But as a society approaches laissez-faire market levels, the people will realise what is happening and will push back away from it. This allows proponents of laissez-faire to say that it would work if only they had pushed it further, but it also stops them from going all the way. In a sense, then, Invictus is right that laissez-faire has never happened. But that's not to say it hasn't been attempted.
Now, as far as regulation goes, I think we are right to point to the "Too Big to Fail" model as a problem. When the first list of banks that were too big to fail came out, those banks all realised that they were no longer responsible for their actions; the government would always bail them out. This gave way to a series of mergers and acquisitions over the years that made them even bigger and fail-y-er.
As for Glass-Steagall, while it is often cited as a cause of the 2008 crisis, I think it's more of a sign than a cause. The Citi Group merger had already gone through; repealing Glass-Steagall was a post-hoc regulatory thing to ensure the legality of Clinton's banker buddies' actions. At any rate, I'm not convinced that more regulation will solve anything because by regulating, you give the people with the most resources at their disposal the most reason to work against what you've just done. Sooner or later, regulation will collapse; I'm sceptical that another Glass-Steagall would fix anything.