There’s something I’ve noticed.
If you steal somebody’s stuff you’re a jerk.
If you’re in charge of some government office or company and you steal from everybody you’re
a stain on society.
But, hit the sweet spot and steal from lots of people all by yourself and get away with
it, and suddenly you’re a hero.
[intro]
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a 30-day free trial at Magellantv.com/jackrackam
London, 1708.
It’s a hard knock life for Jack.
He was lucky enough to survive infant mortality, but his dad kicked the bucket so Jack went
off to a workhouse at the age of six.
The little lad is out to make an honest living and apprentice to a chair maker who ends up
[the chair-maker keels over dead].
So Jack grabs his bootstraps and moves across town to a different chair maker who ends up
[the new chair-maker slaps Jack].
So at age 10 Jack is already having to face a career change, but like his mother always
said, “What would Jesus do?”
so he became a carpenter.
Or apprenticed to one because he’s a child.
This carpenter, it just so happens, knows the muffin man, because he lives just off
Drury Lane.
Drury Lane, which happens to be a real place, used to be a high-end neighborhood but by
the time Jack moved in it was London’s red-light district.
Who knows what that muffin man was getting into.
So when Jack grows up he’s still pale short and stuttering, but he’s street smart and
smooth as butter.
He wooes the ladies at the Black Lion tavern, a hotbed of cutthroats and debauchery.
In fact, he takes a fancy to a lady of the night named Edgeworth Bess and for once there’s
a bright shining light in his life cutting through the London haze.
His days may be filled with sweat and poverty, but his nights become a whirlwind of drinking,
dancing, and romancing.
But that all starts to catch up to him pretty quickly.
He’s showing up to work hungover and snapping at his boss and his money’s starting to
leave him faster than it comes in.
“Bess,” he says, “If I don’t get some cash in me wallet I’m afraid it’s back
to the construction site for good.
And Uber won’t be invented for another two centuries!”
“Ever considered making money under the table?
A little nudge, little pinch” “Why Bess I’m surprised at you!”
“Pick something no one will know is missing.
Quick, easy, and tax free”
“All right Jackie, easy Jackie, nice and simple.
Hello sir, I’m here with the invoice for the work we completed” “Oh yes, let me
grab a pen, let’s see…”
“Nice, nice nice nice, uh, uh, clock, portrait, too big, pen take his pen and run, no,”
“Got it, all right now…” “spoon!”
“What was that?”
“Thank you have a nice day!” “....such a nice boy.”
No one ever caught him for that so he kept pushing the envelope to see what he could
get away with and the heists got bigger and bigger, he brought in Bess and his brother
Tom to fuel his new gang’s burglary spree.
In just a few months he quit his day job invited Bess to move in with him to a street uptown
with the city’s most famous inns and the future homes of aristocrats and millionaires.
Everything was coming up Millhouse until he met Jonathan Wild.
Wild was London’s self-proclaimed thief-taker general, the greatest bounty hunter in the
land.
London’s population had been ballooning and the disjointed police force, or the closest
thing to one anyway, couldn’t keep up with the rise in crime even if its leaders weren’t
taking bribes.
And so the void was filled by Jonathan Wild, a local hero who had exposed the corrupt head
of police and taken it upon himself to assemble a task-force of do-gooders.
Every day he returned hundreds of pounds of stolen goods and brought the thieves who stole
them to justice.
So he sits down with Jack and says he wants to hire him.
“As a bounty hunter?”
“Ahahaha, that’s cute.
No, if you want to do crime in this city you’re gonna do it through me.”
Plot twist, Wild was actually the kingpin of the largest organized crime syndicate in
London.
Those criminals he was locking up behind bars were all freelancers or whatever was left
of rival gangs, making him king undisputed of the underground.
Trying to sell stolen goods on a large scale was challenging, so he didn’t.
Just about everything he stole he would return in a few days time for a reward.
And if any of his men had something to say about giving most of their money to Wild,
well then a bunch of evidence on them would suddenly show up at the police station and
Wild would claim another reward for turning them in.
Jack says he’s gonna go it alone, and Wild says “you’re gonna regret this.”.
In a run of bad luck, Jack’s brother Tom gets caught red-handed and because this is
Georgian London they might just hang him, so he squeals on Jack and Bess.
They go on the lamb and Jack runs to their good friend William to sell off his stuff
and get some liquid capital.
Jack stays at the bar to play Skittles with some guy, but when he steps out to take a
leak, he comes back in with a constable.
“Mr. Wilde sends his regards”
But it turns out this is where Jack gets to shine.
He’s a decent thief, but his true calling is escape artist.
While he’s sitting in jail waiting further questioning, he climbs up to the ceiling,
breaks through the roof and lowers down his bedsheets as a rope.
Everybody heard him on the way out, there’s a big crowd come to see the commotion, so
Jack sneaks in, still wearing leg irons, and goes “Look, up there, I think I see him!
By God he’s handsome!”
A few months later he gets to try again!
He gets caught pickpocketing and Bess comes to visit him and the jailers go “Wait a
minute, aren’t you his accomplice?” and they throw her in the cell.
They make it to court this time and get sentenced to prison, but somehow they got a hold of
a file and spent days whittling through their handcuffs until…
“I’ve got it!
Quickly, let’s away!” [break out of handcuffs, dislodge a bar in the window and climb out.
Cut out to them landing in another prison next door.]
“Come on, seriously!
Ugh” [they climb out of that prison too]
New plan, Jack takes up work as a highwayman on the outskirts of town with Blueskin Blake,
I love that all these guys sound like pirates or gangsters or wild west outlaws.
They’re safe outside London, but they’ve still got to make the run to sell their stuff
so Jack goes back to his old friend William.
William asks him “Jack, ye look like shite, whereabouts ye sleepin?”
Jack: “Some wagon off the road, sorry I can’t tell you more than that.”
William: “Ye need some proper shuteye, I’ve got a spare couch, hell ye can take the bed
if you want to, I can’t stand to see ye like this.”
Jack: “Sorry mate, I know you’d love to have me in your bed but I can’t stay long.
Cheerio!”
Wilde: “Do you know where he’s hiding?”
William: “No… but I know someone who might”
So Bess finds herself approached by a stranger one night who offers to buy her drinks.
He gets her talking, she’s venting about everything that’s happened in the last few
weeks and she spills where Jack is.
Wild’s men drag Jack to court on three counts of robbery.
Except there was no evidence for the first one, and no evidence for the second on, so
Wilde goes out and does the job of the police detectives and the prosecution and digs up
a bunch of evidence and gives it to the court before the third case can get thrown out.
“Right, seems here you’re found guilty of breaking and entering.
To the gallows with you.”
Jack now finds himself in the infamous Newgate Prison on death row.
And this time it’s Bess who gets to pull off the great escape.
She brings a friend to go visit Jack, hopefully in some kind of disguise this time, and starts
chatting up the guards.
Jack then slips through the bars, gives the ladies a wink and runs off in women’s clothing.
“I’m still breaking up with you, love!”
Now everyone in London is starting to take note of the man who broke out of prison three
different times.
I mean think about it he’s like if Houdini let someone else design the death traps.
He hit that sweet spot, a handsome cockney man leading a daring life of non-violent crime
who seemed to be invincible.
Jack, however, seems to have bought into that invincibility because instead of skipping
town he goes right back to playing one jump ahead of the lawmen.
He lasted a little over a week.
This time they put him in the most secure room in Newgate, a room so special it had
its own name…
The Castle.
They slapped on his leg irons and literally chained him to the floor, and Jack told them
“Gentlemen, you’ve really outdone yourselves this time.
I mean look, I can just use this and they’ll pop right off” “Nonono!
/ No!
No!
Drop it!”
Meanwhile, Jack’s old partner Blueskin Blake was being tried in court.
Wilde throws a bunch of evidence at him that’s entirely inconsistent with the evidence he
used to imprison Jack, but the court says “Close enough.
To the gallows, ta-ra!”
“Well, shoot, I guess if I’m going down anyway… hiyah!” and she slashes Wilde’s
throat in the middle of the courtroom.
This courtroom, it so happens, was right next door to Newgate, and all the guards are on
red alert scrambling to contain the situation next door.
So Jack quickly picks off his handcuffs and the extra chains they slapped on him, although
the leg cuffs wouldn’t budge so he had to climb with them up the chimney, dislodge the
bar in the middle, go up through the room they used to keep the Jacobites in, break
through six barred doors into the prison chapel, climb up onto the roof and realize he was
60 feet off the ground without his bedsheets.
Back through the church, past the doors, wave to the Jacobites, down the chimney, grab the
sheets, run up and do it all over again.
After he got out he ended up seeking refuge in a barn and explaining that he’d been
arrested for failing to pay child support until somebody finally took pity on him and
broke off the leg irons.
Now, with that nearly impossible escape behind him… he figured what the hell it can’t
get any worse than that so he goes back to London and broke into a pawn shop to dress
up as a wealthy gentleman and spend some time living it up with a couple mistresses.
A couple days later he was arrested blind drunk on the street.
This time the guards say “Okay, clearly it doesn’t matter where we put you, we just
can’t lose sight of you.
So, we’re weighing you down with a 300-pound weight in the middle of this room in the middle
of the building where we can watch you from all sides.”
Groupies: “Can we watch him too?”
Guards: “Yes, yes, get in line”
That’s not a joke, by the way.
He was such a celebrity that flocks of people came to the prison to visit him and the guards
charged admission fees.
The King’s painter came out to paint his portrait.
People wrote letters to King George asking him to spare this kid from Drury Lane and
eventually the court made a deal with him.
If he’d snitch on his associates he could have his sentence commuted.
And Jack’s thinking was “Nah I’m gonna be out of here in a week and those guys would
kill me if I told on them”.
This time he got closer to the noose than ever before.
He couldn’t do much with a 300-lb weight on him, but they couldn’t bring him to the
scaffold without taking it off.
And if Blueskin Blake could smuggle a pen-knife into a courtroom, Jack could make it work
in prison.
They say as he was brought to the noose a third of London was watching.
And as he’s marching forward, he starts to cut through the ropes, and the guards go
“Ope, almost missed that one!”
They bring him up, put the rope over his neck and drop him, but he’s not dead yet.
He’s strangled for 15 minutes and drops down to the ground, but his friends know that
since his neck wasn’t broken there’s a chance they can bring him to a doctor in time.
But just then someone in the crowd goes “The cops are gonna cut up his body, don’t let
them cut him up!” and they all storm the body, meaning no one could get close enough
to pull him out to safety.
But Jack continued to be the biggest sensation in London because no one had invented the
idea of “too soon”.
His life story made it to the stage within two weeks.
He was in operas, journals, biographies, pantomimes, everyone was talking about the little Drury
ragamuffin who made it big and somehow a burglar became the brave and brilliant hero of the
everyman.
You might rightly wonder why you’ve never heard of him; well, the government felt pretty
uncomfortable about a dead criminal being the champion of the British people so they
wouldn’t let any play with his name in the title hit the box office.
But the floodgates had already been opened, and so while his name faded into obscurity,
Jack Sheppard became an idea.
He became the loveable rogue, the bad boy who won’t be tied down, the renegade fighting
for freedom.
But holy crap does he need to be on Netflix!