The day before, Arthur goes to Doyle's Tavern in Saint Denis to meet Sadie Adler in a solo part of the mission, not including the other Carly and Sadie "niece:", who were left to watch over the hotel room they got in one of the towns.

Sadie tells Arthur about her plan - using a hot air balloon, to scout the prison from above to make sure John is actually still there. The hot air balloon owner, Arturo Bullard, says that Sadie can't go, citing that flying messes with a woman's "vapors". Sadie just laughs this off.

Arthur gets into the balloon and is put in charge of controlling it. Eventually, he reaches the penitentiary, and in the field to the east, Arthur spots a prisoner he confirms as John. Immediately afterwards, the guards begin shooting at the balloon, and Arthur flies away, out of the guards' reach.

On the way back, Arturo Bullard sees Sadie on horseback, getting chased by a gang of O'Driscolls. A rival gang who Sadie has a personal vendetta against after they killed her husband and possibly raped her. Arthur gets angry as was only supposed to return to Carly, and that he only left her an hour ago. He gives Bullard control over the balloon while he begins shooting at the O'Driscolls, in an attempt to save Sadie. At some point during the skirmish, Bullard gets hit, and he falls off the balloon and dies. Saddening Arthur, as he was starting to like the guy.

After this, Arthur manages to bring Sadie onto the balloon. But they crash.

Both Arthur and Sadie emerge fairly unscathed from the crash, but they are ambushed when the O'Driscoll crew find them.

After the O'Driscolls have been eliminated, Arthur reprimands Sadie for recklessly and unnecessarily pursuing O'Driscolls instead of simply checking on the others, which got Arturo killed and endangered herself and Arthur. In response, Sadie changes the subject and asks Arthur whether he saw John, to which Arthur confirms that he did see John. Sadie tells Arthur something else: Colm O'Driscoll has been captured and sentenced to hang. While Arthur is initially dismissive, saying that he had escaped the previous two times, Sadie tells him that she intends to make sure that he doesn't escape this time.