While Ol' Howard is up for discussion, I'd like to check if this does work:
J.W. Byrne, P.I.
Controller React, Boot: After drawing your lowball hand, but before revealing it, boot one of your Grifters at this location. Discard and redraw up to two cards from your lowball hand.
When Howard attaches to a deed as a Condition, he keeps his Grifter keyword. This deed doesn't specify that the Grifter you boot has to be a dude. Can an Ol' Howard attached to J.W. Byrne, P.I. be booted to fulfil the requirements of the ability?