I saw the subject line on my cell phone and was like ... ugh, this can't be good. How on earth did Icthus and I get anointed to be the knowers of things Mafia??
Anyhow, you asked, I'll try to answer. WoT inc.
Like all businesses, the mafia makes money by establishing and defending a profitable market position.
Unlike legitimate businesses, the mafia defends said market position by
a) Breaking the kneecaps of potential competition
b) Generally only dealing in contraband goods and services
c) Bribing government officials to regulate the market position into perpetual monopoly status.
OK, so moving to WoW ... (b) and (c) are really non-starters. There isn't such thing as a contraband good/service in wow for RL/game-world transactions (e.g. selling gold or power-leveling) which does not address the "getting gold-rich" in-game objective that you've laid out. And given that the "government" in (c) would be Blizz itself ... I guess, in theory, you could find some GM (who probably aren't paid that well) and bribe them to manipulate something for you. But I have to think there are huge internal controls at Blizz for that, and there is probably a relatively limited amount a GM could do.
So we're left with the kneecaps. I'll make a case that this doesn't really have potential in the gold-making area, either. Let's take the "shake-down the competition" idea. You're decided you're going to dominate the market for Darkmoon cards. You see some other dude selling them and want to scare him out of it? Like Icthus mentions, you'd need a horde toon to even touch the guy. So in theory you could do that, basically have a horde hit man targeted to take out the competing seller. But if the seller is a bank alt toon ... you're probably not goign to be that effective. Really what you'd want to gank would not be the bank-selling alt toon but the person's main. And it's hard to figure out those links. And someone could easily just create another bank alt toon and become anonymous. With remote auction house, you could buy and sell without even getting in-game. Anyhow, bottom line: even with a horde hit squad, hard to muscle out competiton.
So I don't think there are any mafia lessons for us. I was going to put a sad face emoticon ... but on further reflection, that's not really sad.
On the broader issue ... I don't think you can sustain much of a legit monopoly in the game, period, because there are no finite commodities and there are too many sources of supply. Back in Vanilla, you could in theory pull together a small team to just camp, say, all of the handful of ghost mushroom spawn points. But even then, it was a lot of resources for a commodity with relatively fixed demand. Now, I just don't think that the resource/reward pays off on trying to corner anything. If you do drive up prices, that'll likely just invite competition.
You can get strong market share by being a go-to person for certain crafted goods (like, I'd say, abusedgoat has done for LW ... not that I've ever used him, but he seems to have every pattern and makes sure everyone knows it). And you can make money by knowing prices in certain commodities well, and constantly buying low and selling high. To that end, the guy COULD perhaps create commodity specialists who focus on certain things, to whom the guild gives a certain amount of trading capital to, and then work it from there. But then we're talking about taking the lessons of Goldman Sachs and applying them to the guild, rather than the lessons of Cosa Nostra...