Gentleman Jack

"If the court man asks, you never saw me." -Jack moments before avoiding being served a legal summons
A known troublemaker, the only reason the Guild tolerates Gentleman Jack's antics is because his skills (just slightly) outweigh the trouble he brings. Jack is Lothal's foremost arcane trickster and expert in magical deceit. The Gold-ranked adventurer also holds the Guild's largest personal collection of magic items, many of which are trophies from his skills as a legendary gambler. He's known to treat everything with a comical demeanor that causes many of his colleagues to enjoy his company and see him as something of a mascot. Even with his snarkiness and trouble with the law, Jack is one of the Guild's most loyal members and often looks out for his fellow adventurers from behind-the-scenes.

He Gets Around

The first time the Headhunters spotted Gentleman Jack, he was climbing out of a 2nd story window with no pants after they saw a random man enter the same building. This occurred shortly after a pair of pants fell from the sky and hit Chigiri in the face. Retrieving his pants from his fellow adventurers, Jack used a magic cloak to teleport away after the man came barreling out of the building looking for him.
The next time they saw him, Jack was attending the harvest festival to play a few carnival games and flirt with the local maidens. When Nadira appeared and started causing problems, Jack helped Chigiri back on his feet after the ninja freed himself from her enchantment charm and then assisted with apprehending one of her jackelwere minions. It was at Jack's prompting that Chigiri and Kiri abandoned the idea of torturing their prisoner and turned her into the authorities instead.
Jack later turned in one of the twin lightning swords when Chigiri posted a bounty for the 7 Swords. The Headhunters happily thanked Jack for his assistance in recovering the sword and aiding them in their noble quest. They never learned that he robbed a museum in Nerograd to obtain it. Shortly thereafter, they did learn that he was one of the handful of adventurers with the good sense not to use a Gravestone.

Spying on the Morlocks

When a court official representing a collective of angry husbands started waiting around the guildhall to serve Jack, he decided to hide out in the Giantsheel Mountains. Ever wary of legal representatives, his keen senses allowed him to dodge a greater threat lurking in the mountains: the Morlocks. Jack very quickly realized his excursion was going to be far more important than originally planned.
Jack snuck past patrols of Molders, Shadow Skulls, and druegar as he made his way up the mountain, both via cliff climbing and through the tunnels. He used a magic orb to record what he saw, culminating in spying on Moltor and Mesogog as they discussed the final stages of the Gravecannon's completion. Unfortunately, he did not escape Mira notice and she gave her allies subtle signals that they were being spied on. Jack was quickly made aware he was compromised as Levira emerged from his shadow to attack, forcing the arcane trickster to flee.
Teleporting with his trusty cloak, Jack got outside the mountain and summoned his hawk familiar to get the crystal orb back to the guildhall. He then began the difficult task of dodging the Morlocks' forces until reinforcements could arrive. They eventually came in the form of Shimmerscale, who rescued Jack just as he was cornered by a group of Shadow Skulls led by a Void Beast. Riding the dragon to safety, the pair headed to the mountain peak where they picked up the Headhunters and the captured Moltor.