Why are you (apparently) calling Milton Friedman a sycophant of monopolists? Here's a Friedman quote, shortened to keep it on topic:
"A government which maintained law and order, defined property rights, [long list of other functions of government,] engaged in activities to counter technical monopolies and to overcome neighborhood effects widely regarded as sufficiently important to justify government intervention, and which [something about welfare]—such a government would clearly have important functions to perform. The consistent liberal is not an anarchist."
Obviously he didn't like regulation at all, and was probably struggling to decide how much of it to tolerate, but that doesn't mean he wanted monopolies.
I was thinking more of Scalia than Friedman, but let's go there for a minute too.
Probably nobody wants monopolies except for monopolies; the question is what do you do about them? And the Chicago School answer is something like, have more free trade and fewer regulations so that markets are more competitive.
The problem with this is that it isn't robust against selective implementation.
We get "free trade" where international corporations get access to US capital markets in order to fund the creation of vertically integrated global supply chains that offshore jobs and consolidate the global economy into a small number of companies and countries, but we don't get "free trade" where US consumers can feasibly use a foreign bank or payment processor if the US ones have consolidated and captured the regulators, or where foreign doctors have a practical path to immigrate to the US and practice medicine.
We get "fewer regulations" where giant corporations successfully lobby to get rid of laws that are inconvenient to giant corporations (like Glass–Steagall), but not "fewer regulations" where there are still a zillion regulations that impact small companies more than large ones and make it more difficult to start a new business or compete with existing incumbents. I mean, why is DMCA 1201 still on the books? Its nominal purpose was a fraud from day one and the only thing anybody really uses it for in practice is to lock out competitors.
You thereby accumulate a bunch of consolidated markets that you need to promptly smash into tiny pieces with the antitrust hammer or you're in a losing battle against time where they lobby to accumulate even more rules that benefit the incumbents faster than anybody else can accomplish getting rid of them.
And I know I'm criticizing the implementation rather than the theory here, i.e. Scalia rather than Friedman again, but for a theory to be good it's kind of important that it be amenable to practical implementation.
But for that you need the theory to actually specify -- in bright letters on the front page, not in a footnote somewhere -- that the most important part is that the regulations you get rid of first are the ones that limit competition, not the ones that defend against consolidated incumbents. Because otherwise the consolidated incumbents will point to your theory to argue for doing the opposite, which is what happened.
"A government which maintained law and order, defined property rights, [long list of other functions of government,] engaged in activities to counter technical monopolies and to overcome neighborhood effects widely regarded as sufficiently important to justify government intervention, and which [something about welfare]—such a government would clearly have important functions to perform. The consistent liberal is not an anarchist."
Obviously he didn't like regulation at all, and was probably struggling to decide how much of it to tolerate, but that doesn't mean he wanted monopolies.