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Penelope was a pilot who founded the ACES competition, who flew and fought under the alias "Black Baron." During her career as the Black Baron, she gained both fame and infamy. She was later exposed by the Cooper Gang, after which she joins them as their RC specialist.

Background
Little is known about Penelope's early life. As her interest in fighting grew, she invented a disguise she called the "Black Baron" to get past competitions' strict age limits. The Black Baron soon became a celebrity, and Penelope found her wearing the costume and assuming the alias more and more often. At some point, Penelope wanted a challenge to her expert skills. So, she set up a yearly international competition called the ACES in an effort to attract worthy opponents.

Meeting Bentley
While Bentley was trying to think of a way to get into Dr. M's, he finally came to the conclusion that in order to do so, he and the gang needed the help of an RC specialist with skills much greater than his own.

After spending weeks searching through chat-rooms, Bentley finally found someone who was able to keep up with him intellectually, who called herself Penelope. Bentley asked her if she was interested in helping out, telling her about his gang's notoriety and opulence. She didn't seem convinced by this, explaining that she only worked for "the best." She considered "the best" to be people as good as her boss, the Black Baron. She told Bentley of his talent and how he held his own competition, and that she would only join the gang if they could beat him at his own game. Bentley accepted, and they headed out for Holland. Unbeknownst to him, however, Penelope was the Black Baron.

Defending the Hangar
After the Cooper Gang arrived in Holland with their newly built biplane, they immediately set up shop and a hangar to get ready for the ACES competition. They also framed teams Iceland and Belgium for doing the other harm, to give themselves a fighting chance. During their operations, Penelope informed Bentley of a rumor she had heard that a rival gang was coming to do harm to the gang's plane. Just as Bentley finished setting up the hangar's security systems, the hangar was attacked. Bentley used the defenses to take care of them, but as more were coming from above ground, he called Penelope for backup. Penelope brought out her RC chopper and used its new feature, the Yank 86, to take out the last of the attackers.

Secret Exposed
"I guess someone was bound to find out sooner or later."

- Penelope, after Sly exposes her.

After Team Cooper won the semifinals of the competition, they moved on to the finals, which put them against Team Muggshot and Team Black Baron. Penelope commanded a large fleet of pilots that would assist her. To thin out her ranks, the gang used a giant wolf to attack them. After that, they also got rid of Muggshot to avoid him causing trouble in the air. They also gained control of the aircraft control tower to intercept any messages Penelope might send to her large gunships.

Before the finals, Murray destroyed the aircraft control tower, which would force Penelope to resorting to using an unscrambled radio frequency to call in her gunships. After that, Sly suited up took to the skies. As soon as he spotted the Black Baron, he went for him.

When Penelope's biplane finally took an ample amount of damage from Sly, she decided to call in her gunships along with a spare plane. As she was talking through the radio frequencies with the gunships, Bentley intercepted and told her that she was going to have to play fair this year. As Penelope was expressing her confusion, Bentley sent out his secret weapon. Penelope commanded Bentley to stop as a windmill wheel detached from its mooring and flew straight into both gunships, destroying them.

Penelope then ditched her plane and jumped to the wing of the spare airplane. Before she could walk inside, she was confronted by Sly, who explained that she had lost as her biplane was in pieces. Penelope rebutted this by stating that they were still airborne, and they fought. As they did, she called upon her guards to help her, but Sly defeated them as they came. Eventually, Sly struck Penelope and knocked her mask off, exposing her. Sly was confused and asked Penelope why, but Penelope suggested that they get to safe ground first.

When they descended, before Penelope could explain at all, the gang and her were rushed to the winner's circle, where Bentley and her looked at each other awkwardly because of the difference between their real-life selves and the photos they posted on the internet. Later, Penelope explained her back-story to them, but with her past career now out of the way, she was free to do something new, and she joined the gang without hesitation.

Ur Mom
After the ACES competition Penelope helped the gang during their operations in China to rescue Jing King. During one of her aerial sweeps of the area around the hideout, she picked up an strange radio signal coming from a nearby river. Murray was the one to go and investigate it. It turned out to be the Cooper Van, frozen in a block of ice. Penelope used her RC chopper to drag the van to dry land, where Murray broke it out. She tried to explain to Murray that it was too dangerous to try and drag the van back to the hideout, but Murray was intent on doing it. She kept the incoming guards away from him as he dragged the van forward. Eventually, Murray was halted by a wall of spikes, and destroying them was out of Penelope's ability. Just then, the Panda King helped Murray through the spikes and the last wave of enemies, until he finally brought the van to safety.

Down the Line
Later on, Penelope guides Murray to a strong box, which was the main router for the area's phone lines. She told him to open so she could come and reroute them. As Murray opened the strong box, he was knocked out by poisonous gas. Penelope hurriedly made her way over there, but Murray was already gone. Not being able to get to him on foot, she used her RC car to follow the fuse on the trail of gunpowder. She managed to outrun it and got to Murray before he was blown up.

Skull Keep's Wrath
In Blood Bath Bay, Penelope accompanied Bentley to Skull Keep

Fighting LeFwee
As shown at the end of Sly 3: Honor Among Thieves, Penelope helped Bentley create a new Cooper Vault, assisting in adding more technological safeguards to the upgraded vault to ensure the safety of the riches that the team had worked so hard to acquire. Also, emblazoned upon the vault door were the images of the original Cooper Gang trio.

Skills
Penelope is

Penelope is an ace pilot, to the point of achieving near-legendary status as the Black Baron. She is equally adept with RC planes and cars, and she designs, constructs and modifies them as well as operating them. Like Bentley, she is extremely intelligent (Sly remarks that when the two talk, their conversations go over everyone else's heads) but her expertise is less on the planning and hacking side of things, and is instead focused on the mechanical. She also seems to have picked up some swordsmanship skills somewhere, as shown when she successfully dueled Captain LeFwee and some boxing skills as well, shown when she fights Sly as the Black Baron.

Personality
Despite trying to kill Sly in the ACES tournament, Penelope is a very nice person. She enjoys utilizing her RC talents against enemies, and while doing so usually gets slightly over excited. While Penelope had only been a member of the gang for a short time, she was dedicated to her new-found friends, eagerly supporting them whenever they needed help. Unfortunately, her lack of physical prowess makes her rather timid when actually confronted by an enemy, but when someone she loves — namely Bentley — is threatened, she becomes a powerful combatant.

Romantic Life
Penelope's love life is played upon humorously throughout the game. As illustrated Bentley's his wide-eyed drooling expression on first seeing a picture of her, he is infatuated with Penelope from the start, much like his friend Sly is with Carmelita. When they finally meet, the pictures they shared of themselves prove to be rather inaccurate and Penelope quickly turns her attention to the athletic physique of Sly. Bentley seems disappointed and disinterested but his interest returns over time as Penelope proves her intellect. However, after Bentley is threatened by LeFwee she realizes she holds strong feelings for him, leading her to heroically saving him and defeating the pirate. After the gang disbands Penelope and Bentley stick together to help rebuild the Cooper Vault.

Trivia

 * Penelope and Carmelita never see each other, not counting the postcard that Sly sent to Carmelita with the gang on it.