Like a Moth I use quite a bit to use Bound and Gagged on big nasties (Y'Golonac, Cthulhu, etc.) and for stalling rush decks. I will concede that Smugglers > CC Bootleggers.
I would probably ditch CC Torch Singer and opt for something else. Is there something that SY/ST offers to help deal with Fanatics and Widows? Or would it be worth throwing Widows in myself?
Like a Moth + Bound and Gagged, while a good move on the fly, is probably not a good idea for "why its in the deck." If you get my meaning. You're using 2 cards to stall out 1 character(not too great for your card economy). I say stall because it unless you keep your Initiates in the grip you'll likely let loose the baddie you have tied up.
As for the "free" characters.... Are there things? yes. any good ones? not really. Your best option was Diseased Sewer Rats, now, not so much.
Unbound - Discarding 3 cards to destory a skill of 2 is... harsh. Combos well with Torch Singer actually(as you'd only be discarding Unbound itself if you can lower the skill enough).
Vengeful Mob - Requires some work, but possible.
Secret Stiletto - Again requires work, but triggers off of you winning by overcommiting instead of losing by undercommiting. But they'll see it coming.
The Mage Known as Magnus - Less work, but wound need to warp you deck to field stuff above cost 3 which is not recommended.
Ice Shaft - Its not cheap but it gets the job done.
If you keep the skill reduction around, Unbound doesn't look to bad. Otherwise Ice Shaft is likely the best option.
As for using a Rich Widow yourself. Depends on how rushy you feel. If you feel rushy they by all means add it. If you feel very rushy I'd add your own dreamlands fanatic. If you feel very very rushy look at Servant from out of time and/or Furitive Zoog (sometimes I think I'm the only one in the whole world that likes/uses these cards).
However, I'd add a Fanatic before I would a Widow. Turns out free 2-fast-TA icon characters with 2 skill that get around Negotium are good.