From what I've gathered the Outfit ever since it's big bust in the 80's with the Casino's leading to the murder convictions brought up in Family trials, the mob in chicago probably want to have a break and just keep low key and carry on traditional mob crimes. Such as gambling, Loan Sharking and extortion. It is also said to be involved to and extent still in the unions and has many legitimate businesses. Numbers wise I'm not sure what to make of it, I suppose 30 members and 100 associates sounds right, but I did expect more since wasn't the Chicago mob in the 80's bigger than the Philly mob in the 80's? And now they are the same size?
Recent indictments also show how they were involved with a Biker gang performing robberies. Also that cop was arrested for involvement in a national scale jewelry theft ring. If you ask me, they still got some good money makers going on, but no drugs to keep the heat off. This way they will probably start to rebuild slowly but probably keep the numbers down as well..
People forget how hard the Outfit got hit in the 1980's and 1990's. Relatively speaking, as much as any other family. And though it may have been larger than, say, Philadelphia in the past; I'm not sure the difference was that significant. In my opinion, a lot of the estimates we've seen for Chicago in earlier decades were inflated. And both in the past and today, I think the difference in Chicago is more the member-to-associate ratio than overall manpower. As for the actual members themselves, the Outfit started using the ceremony later on and seems to be much more careful about who they let in. They're more about keeping a smaller core and a low profile than keeping a certain membership quota. It makes for short term quality but can hurt long term viability in terms of general attrition.
In terms of their rackets, gambling (bookmaking and video poker) is their main business, just like the New England or Philadelphia families. Loansharking also. Extortion? It's probably a safe bet that certain things like independent bookies and mob-connected burglary rings pay the "street tax." And maybe certain businesses like strip clubs or porn shops. But I don't think there's a widespread shaking down of legit businesses in Chicago today. And the Outfit doesn't have the muscle to take a piece of any and all criminal activity. As you said, they have very little interest in narcotics. And, while there's still some influence, over the last decade there's been limited activity in labor union racketeering. Of course, there are Outfit guys who have legit interests - construction and trucking companies, real estate, restaurants, etc.
