I've been thinking that Jackson needs to thread with either Sunny or Snow, and since Snow is much more likely to punch things until her knuckles bleed after losing Kash, probably her.

ALSO

Mildmay, always, because of course
Tony, because genius manchild alcoholics
Regina, just because it's funny
John Smith, because 1913 is much closer to 1890 than pretty much anybody else
Quill, again because manchildren