Chekhov MacGuffin wrote:The topic of Bourbon's mission comes up one more time other than the scene with Jodie and Hidemi on the cellphone. Hidemi brings it up with Gin and Vodka in the Porsche during the red shirts case.
(703.03) Technically, I suppose it is speculation since Gin and Vodka neither confirm or deny Sherry-hunting is Bourbon's mission, but it seems likely since dressing up as Akai
isn't what Bourbon is supposed to be up to. I doubt the boss would have given permission to take out "Akai" if
that person had assigned Bourbon to scope out the FBI in disguise. I think Vermouth may have known/guessed what Bourbon was up to which is why she made a comment about the boss being cautious enough to testing a stone bridge - a tip to Gin to not be too trigger happy without careful assessment first.
Wow...based on that page from the manga, I'm going to throw this out for fun:
Bourbon was Akemi's boyfriend before Akai/Dai showed up in the BO. He hates Akai for stealing her away and blames her eventual death on him. He had plastic surgery to make him look like Akai due to his obsession, i.e. he either is trying to draw him out b/c he thinks Akai's not really dead or is obsessively insane or some mixture of both. Maybe he gave himself the scar when he looked in the mirror after his surgery and saw the face of the person he hated most...and he lost it and somehow hurt himself.
Alternative theory:
Bourbon was someone who was competing with Akai/Dai for position in the organization. He always lost to Akai, and became obsessed with beating him, and that's why he's obsessed with being "the only one who can kill him". Again, a combination of mad obsession and strategy led him to change his face to Akai's (similar to the guy who took Shinichi's face in the story with the shiragami?), and he couldn't stand his own face and scarred it.
Okay, really reaching here:
Maybe Gin already knew Bourbon had Akai's face, and the whole thing was a test for Kir and to draw out Akai. The "I'd rather not see him with such a face" was referring to Akai's face...
...maybe...possibly...okay, maybe not...

Three Mafiosos can defeat a Zhuge Liang.