Jack

"It’s weird for me to be saying this, but we were such lousy jerks that just looking at us would make you want to beat us to death… If the me from now met the me from back then, I wonder what I’d do with him. Would I beat him to death, or would I quietly hug that brat close and sob like an idiot?"

- Jack, reflecting on his and Nick's childhoods

Jack (ジャック Jakku) is one of the delinquent members of Jacuzzi's Gang who participates in the robbery of the transcontinental luxury express Flying Pussyfoot between December 30–31, 1931. He is brutally assaulted by Ladd Russo during the journey.

Though he makes a full recovery from the beating, he still holds a grudge against Ladd four years later in 1935 and intends on having his revenge after Ladd is released from prison.

Appearance
Jack has short hair (white in the anime), and in the anime wears a muted light purple jacket over a black shirt and black trousers. His clothes are cheap-looking, and he has the overall appearance of a delinquent.

Personality
Jack is hot-headed, aggressive, and one to hold a grudge. He seems to have had a bit of an arrogant streak before joining Jacuzzi Splot's gang, which has tempered slightly in the interim.

He does care for his fellow gang members despite using slightly judgmental language to describe them, given that he tries to convince Fred—perceiving him to be the Grim Reaper—that he can still go save Jacuzzi and the others despite being terribly injured.

Pre-1931
Jack grew up in one of Chicago's impoverished tenement slums with his parents, who both died of malnutrition while he was still a child. Unable to afford burials, Jack was forced to bury his parents under the floorboards of their room—an experience that he still vividly remembers years later.

After the deaths of Jack's parents, Jack teams up with Nick, one of the 'neighborhood brats', and they get into all sorts of trouble as public nuisances.

1931-1932
Jack and Nick eventually meet a teenager by the name of Jacuzzi Splot sometime in the middle of the year 1931, and learn of Jacuzzi's plan of making bootleg liquor and attracting more people to his burgeoning gang. Disparaging Jacuzzi as a "lame, snivelling punk," Jack joins Jacuzzi's gang with designs to eventually usurp Jacuzzi and turn the gang into his very own mafia outfit. However, as Jack spends more and more time with Jacuzzi he comes to understand that Jacuzzi is the 'smartest' of the whole lot and far too kind to ever think of actually abandoning the gang. Jack's grand aspirations of usurpation fall to the wayside as he finds that Jacuzzi is simply too nice to betray.

Half a year later, Jacuzzi's gang murders the Russo Family capo Sidaris and two other Russo men on the night of December 29 as part of their vengeance against the Russos for murdering eight of their friends. In the ensuing hours, Nice Holystone handpicks Jack and Nick as the final two gang members joining her, Jacuzzi, and Donny for their train robbery aboard the transcontinental express Flying Pussyfoot.

On December 30, Jack and the four other delinquents meet up at Chicago's Union Station at 4:00 PM and board the Flying Pussyfoot's sole third-class carriage. They settle into their compartment, and the train is soon off, eastbound for New York. A little while into their journey, Jack reacts to Jacuzzi's comment on their 'great view' by asking if he is really going to steal the Flying Pussyfoot's cargo after all. He grows increasingly irate at Jacuzzi for apologizing and then for retracting his apology; then, he demands that Jacuzzi pull himself together, pointing out that Jacuzzi could have stayed behind while 'tough guys' like Donny and Jack take care of the dirty work. He concludes that if Jacuzzi is their boss, then he should think about what his own life is worth.

Nice and Jacuzzi leave to make contact with fellow gang members Jon Panel and Fang Lin-Shan in the dining car, where they are working as staff. Some time passes, and Jack, Nick, and Donny eventually leave the compartment to go join the others in the dining car. They are startled when Jacuzzi bursts out of the dining car and runs past them on the outside platform, screaming something about needing to find the Young Conductor before disappearing into a second class carriage.

Nice emerges onto the platform a moment later, explaining that Jacuzzi's going to the conductors' compartment and she's on her way to bring him back. She orders Donny and Jack to come with her and check on the freight hold containing the special cargo they plan to steal (high-grade smuggled explosives) along the way, leaving Nick with the instructions to 'take care of the dining car.'

The trio move through second class and third class, and when they reach the freight cars Jack announces that he'll go ahead and tie up the black-suited men guarding a freight room, and runs ahead into said room. Nice and Donny wait for him in the second freight car, but he does not emerge. When they investigate, they find a machine-gun toting Black Suit shepherding Jack outside of the room—and that Jack's hands are tied behind his back.

Jack is tossed into the second freight room, and a man and woman both clad in white soon join him in bound captivity. When the room's door opens again for the third time, it opens to the machine-gun toting guard leading Nick, bound, into the room. Nick joins Jack on the floor, and they try and fail to strike up conversation with the White Suits. Then they try to at least chat amongst themselves, but a glare from the guard nips that idea in the bud.

Eventually the guard leaves the room, and in his absence Jack and Nick futilely struggle to until themselves. The guard does not return; in his stead enters the White Suits' leader Ladd Russo, who strikes a pose and immediately runs over to untie his fellow White Suits, clearly romantically involved with the woman Lua. He dismisses Nick's and Jack's plea for him to untie them as well, tauntingly suggesting that it is the men's destiny to die where they are. Jack, easily provoked, starts yelling at Ladd's retreating back.

Nick tells Jack to give it up, addressing him by name—and this proves to be a massive mistake. Ladd immediately reenters the room to untie Jack's ropes, chattering away about wanting to see whether all 'Jacks' are inherently good at boxing. Without further ado, he begins whaling away on Jack, driving punch after punch into his face. He only stops at the sound of gunfire from some of the cars up front, at which he finally leaves with his friends in tow. Had he continued assaulting Jack, he would almost certainly have killed him.

In horrible pain, Jack can do little more than hunker down by Nick—who is still bound—and wait. They are eventually rescued by Nice, Jacuzzi, and Donny, all of whom are furious over Jack's wounds—Jacuzzi especially, who 'switches on' after hearing Nick's explanation over what happened. He is so worked up that he takes it upon himself to initially carry Jack over his shoulder, though Donny quickly takes over for him.

The delinquents move into the first freight car, where they find Ladd and the others exiting the first freight room. Ladd looks over at Nick's shout, and when he introduces himself with his full name—Ladd Russo—the delinquents immediately tense. Their confrontation ends once Ladd and company leave to investigate the conductors' compartment, leaving Jacuzzi and the gang to investigate the bloody mess in the first freight room—a legless corpse of a Black Suit, with blood on the ceiling and the floor—that Ladd claims the White Suits aren't responsible for.

Out in the corridor, Nick calls everyone's attention to the window. On the count of three, everyone (except for Jack, still slung over Donny's shoulder) look outside and spot a red shadow moving outside the train. Jacuzzi, Nick, and Nice decide to travel over the third class carriage via the roof while Donny carries Jack down its corridor toward the front of the carriage. The exit door opens to reveal a couple dressed straight out of the Wild West. Donny and the couple stare at each other, and then the man excuses himself and closes the door.

A nervous silence ensues, until the duo—Isaac and Miria—timidly ask if Donny is the Rail Tracer. Surprised, Donny asks if the woman (Miria, whose dress is colored blood-red) is not the Rail Tracer. Both groups soon realize that none of them are the Rail Tracer, much to their collective relief, and Isaac and Miria enthusiastically reopen the door to chat with Donny for a little while before continuing on their way to the conductors' compartment.

Donny and Jack are soon joined by their friends on the connecting platform, who report no signs of the red shadow. The five delinquents make their way through the second class carriages, and wait while Nice peeks inside the dining car. She reports that all the passengers at the bar that she and Jacuzzi had made friends with are now missing, including the flamboyantly dressed Isaac and Miria. Donny finds her description of them 'weird', until Jack moans and reminds him that they ran into Isaac and Miria only a few minutes ago.

HIs memory jogged, Donny explains to Jacuzzi that Isaac and Miria said they were going to the conductors' compartment to save a 'friend' from the Rail Tracer. Realizing that they meant him, Jacuzzi orders his group to split up. Jack interjects and suggests that they leave him in one of the passenger compartments, since carrying him would only hinder the others' movement. They have no choice but to agree, and Jacuzzi and Donny settle Jack in room three of a second class carriage before hurrying toward the rear cars.

Alone, in pain, and thinking that he might die, Jack reflects on his past and the rest of the gang, calling them all—including himself—idiots. A mass of grey enters his field of vision—which is severely limited thanks to the his swollen eyelids—and Jack takes the figure to be the Grim Reaper. Jack claims that he is fine, and that all he needs is a little rest before he goes off to save Jacuzzi and the others—and he has to go save them because he's the best the team has. He asserts that Death had better not take Jacuzzi by mistake (since Jack will save Jacuzzi, after all).

Admiring Jack's will to live, the grey magician—actually Doctor Fred—opens his medical bag and begins treating him (unbeknownst to the two of them, the Rail Tracer is watching outside the window). Not long after, the door to the room opens and in walk Lua and Who, the very same White Suits whom had been in captivity with Ladd. Though initially wary, Who helps Fred move Jack to the bed and assists him with medical treatment.

Once the train arrives in New York on December 31, Jacuzzi and Jack are taken to Fred's Clinic for further treatment and recovery. The two lie in adjacent beds, and spend the next several days recuperating.

In the anime, Jack heads to an abandoned factory with the rest of the delinquents to support Jacuzzi in his face-off against Graham Specter in January 1932. By this time, the majority of the gang, including Jack, have moved into the Genoard Family's manor on Millionaires' Row.

1933—1935
In September 1933, Jacuzzi's gang is roped into helping Tim and the Larva infiltrate the Mist Wall by gassing its employees with sleeping gas and distracting security, disguised as janitors. Jack and Nick are two of the delinquents who dress up as janitors and participate in the plan. At one point during the infiltration, Lamia member Hong Chi-Mei exits an office and notices Nick and Jack crawling across the floor at the end of the hallway. Observing that Chi is standing, Jack and Nick suppose that the gas hasn't reached their floor yet and get to their feet accordingly. One of them takes note of Chi's strange appearance and asks if he is one of Tim's reinforcements, but he doesn't respond and races down the hallway in the opposite direction.

Over a year later, Jack and the rest of the gang return to Chicago in December 1934 in order to help Miria reunite with Isaac and potentially help Graham, whom they've heard has run into trouble there. The gang is quickly caught up in the chaos in the city, including a series of bombings for which the local police suspect Nice to be the culprit.

Nice, Miria, and Rail end up being kidnapped by members of the Runorata Family, who spirit them away to Nebula's headquarters. While the rest of Jacuzzi's gang mount a rescue (along with Graham's people and Christopher Shaldred), Nick and Jack are sent to Union Station to pick up Isaac, whose train is due to arrive that day.

Nick and Jack hightail it to the station and frantically look for Isaac, hardly pausing to catch their breath. Nick panics when he sees that the train to New York is already bound to depart, but Jack is more concerned with how Isaac will react when they him that Miria has been kidnapped. It turns out that he doesn't have to worry, because Isaac is nowhere to be found.

A couple months later in February 1935, Jack overhears that Ladd is due to be released from prison in a few days. His grudge rekindled, Jack occupies the time by practicing boxing against a punching bag in the Genoard manor—fully aware that doing so will improve his chances in a fight against Ladd exactly nil. Nick eventually approaches Jack after the few days are up and tries to talk him out of his need for vengeance, without success.

Nick leaves Jack to his boxing, and he returns to the room with Nice in tow. Still punching the bag, Jack tells her that he is entirely serious about his plan and will not rest until he beats Ladd to a pulp. Nice reminds Jack that Graham promised to mediate between Ladd and the gang, but Jack is unmoved and tells him to stay out of the situation—he and Nick will take care of it by themselves. Nick protests at Jack dragging him into his own conflict, and when Jack claims that he was "kidding" and that he will "do it on [his' own," Nick points out that there is no possible way Jack can beat Ladd in a fight.

Jack argues that winning or losing isn't what's important, it's his pride, without which he will never be able to fight again. Having had enough, Nice sends Nick out of the room to fetch Jacuzzi, Donny, Jon, and Fang—all the gang members (excluding Chané) who were on the train. She says to Jack that if he really is going to go through with his revenge, then the rest of the gang will help him even if it means destroying Graham's and Jacuzzi's friendship. Jack protests that this is his business alone, but Nice retorts that even if Jacuzzi is completely against Jack's plan he'll help Jack out no matter what.

Nick returns with the news that Jacuzzi and Rail left with Isaac and Miria, the latter of whom are on their way to ask Molsa Martillo for a job. Jack catches Nice's bomb as it slips from her fingers.

Trivia

 * While Jack is cut from the hijacking team in the 2007 anime, he makes a cameo in Episode 01 as part of the retrieval team and later reappears in Episode 15.
 * In the English dub of the 2007 anime, Jack is voiced by Tyler Walker, Funimation's ADR director for Baccano!. Tyler also voiced Vicky.