IMO, there's a few reasons for this.

The Outfit has always been very different for the fact that they are the only thing in town. So I think "official" numbers are different than in NYC. One thing for sure, they have gotten smaller.

They used to have 6 crews and now I've read they are down to 3 or 4. It's been listed, like someone else said, that they they have 25-35 made guys and one hundred associates. This again is confusing because The Outfit makes very few people and knowing who is made is confusing because in the change of them not having a ceremony (not having a ceremony, to having a ceremony, to who knows), so being made can be confusing. Some people think Nick Calabrese made up the making ceremony he testified to and others have said they never got a pin prick or the such.

With the Outfit, being made is like being a Capo in NYC and being an associate is like being a soldier. So is that 100 associates, made guys and workers or just random guys, like bookies and such? Probably somewhere in between.

The Outfit also, from what I have read, has gone extremely low key and quiet since DiFronzo took over. It appears that this seems to be by choice. So is it by choice or is it because they are just really weak?

Also, the outfit is the only thing in town. Like others have said, in NYC the more made guys you have the more powerful the family. I have always thought that if there is no competition why does the number of made guys matter? If I'm the outfit, I stop making guys. They survived for 50-70 years without having a ceremony, why not just stop making people? In thirty years, you'll have no made guys. You'll be "dead".

Like another poster said, I have read that the outfit has been cut into 2 groups, north and south. That the north, run by Difronzo, has gone extremely low key. That DiFronzo doesn't want anybody doing anything that could get him in trouble. They say he makes a ton of money and doesn't want to risk it. Then in the south you have the more traditional crews, doing the work. And the north and south have little interactions. People really don't know who is in charge. Is this split the reason? Are they being sneaky or are they just weak?

Looking at the history of the outfit, even people being made have been a big argument amongst people and police. In NYC it seems people know who the made guys are. Cops and mafia fans, but in Chicago it always unknown. It's been like that for a very long time. It's just secretive. One made guy has ever flipped. Just a different type of thing.

There was a guy that they (FBI and papers) said was extremely high up, who the FBI didn't even know was supposedly made, Al 'Pizza Man" Tornabene. Guy died in 2009, no police record, supposedly was running parts of the outfit. Secretive or is this a sign at how weak the outfit has become? Could see it both ways.