Bentley: Now the roster is kept secret from the pilots but not from the event staff.
Sly: Do we have a mole on the inside?
Bentley: Our "friend" Dimitri has been hired to give color commentary during the dogfights... He'll know where the roster's hidden.
― Bentley and Sly on how they plan to acquire the ACES Team Roster
After settling into the hotel, Sly dressed up in a pilot disguise and headed down to the lobby,[note 1] where Bentley gave him the brief on their operation. The place was packed with pilots who would be competing in the ACES competition.
If the Cooper Gang hoped to be successful in the competition, they would first need to learn who their opponents were. Bentley explained that in the past, teams would go out and sabotage each other's planes, in preparation for an upcoming dogfight. To prevent another incident, the flight roster's location was now kept a secret. The flight roster was, however, not hidden from the event staff. Fortunately for the gang, Dimitri had been hired to give color commentary during the dogfights and was sure to have knowledge of the roster's whereabouts. Sly scouted him out in the hotel lobby. Bentley warned Sly that starting a fight with the other pilots would disqualify the team from the competition.
Once he found Dimitri, Sly had him reveal the location of the roster. However, Dimitri refused to talk for fear of being exposed to the Black Baron and losing his job. Sly offered him a bit of encouragement, saying that a guy like him could deal with the Black Baron, as he had the best fashion sense of anyone he knew. After hearing this, Dimitri showed renewed pride in his ability to outsmart the Baron. He then agreed to disclose the location of the roster, on the condition that Sly agreed to owe him a favor, which would be returned in a few months. Sly accepted the bargain, then Dimitri told him to search the Baron's air hangar and look behind one of the paintings; it was kept in a secret safe.
Before Sly left the hotel, the Black Baron walked into the lobby to welcome all of the pilots to another year of the ACES competition, especially the team led by an old foe, Muggshot. He then reminded everyone about the hi-jinks some teams pulled off in the past, and that he would no longer tolerate it. He explained the rules of the hotel, specifically of the consequences for leaving the hotel after sunset. He then bade farewell and left the lobby. Sly left as well, with Bentley warning him to be careful once outside.
Sly took off his disguise and made his way up to the Baron's castle on the far hill. Once there, he needed to find a way in for Bentley. Since the drawbridge was up, Sly needed to perform some skillful climbing to reach the top and find a switch. Along the way, Sly overheard the Black Baron pondering about how much tougher the competition had gotten, with a slight hint of worry that he might not win this time. Once Sly reached the roof, Bentley showed up and asked him to lower the drawbridge. While there was no switch, Sly noticed a catapult and sent it down to Bentley. Bentley used it to launch up to the roof.
Sly headed back to the safe house, leaving Bentley to finish the job. Once inside the Baron's hangar, Bentley inspected both paintings. During the inspection, the Black Baron made an announcement on the intercom to warn his guards not to hand him his first loss. Bentley found the roster in the second painting he unlocked and stole the roster before returning to the safe house.
- When selecting Sly after the gang enters the safe house, this job is started immediately. A unique cutscene will play where Sly will walk from the table to the hotel room's door, change into his pilot outfit, and exit the room. This is not seen when replaying the job.
- Both paintings in the Black Baron's hangar are of the Indian jungle from "The Predator Awakes" of Sly 2: Band of Thieves.
- Unlike on other art decryption lock paintings, the combination (which in this case is 223) appears on the painting of the spice temple twice.