Hewlett Bay Park, New York

December, 1963

Jane Sterling was walking down the stairs of her home when she noticed the front door was cracked open.

Roger had come in late in the night, slumped over on the bed beside her in his clothes and laid face down. Jane woke for a moment when he fell, she pushed him to see he was alive, and left the bedroom in her robe. The hall was freezing, there was some snow that had blown in through the crack in the door.

Jane ran up to the door and closed it quickly.

"Roger." She scoffed, moving her hair out of the way, and began moving back towards the grand staircase in the house. She stepped up but noticed the door to the study was open. She turned, moving towards the study to pull the door closed.

There was a slumped figure in the corner. It shocked Jane and she let out a light scream. The figure didn't move. She moved closer, quietly, with great curiosity. It was a young girl, perhaps just a few years her senior. She reeked of alcohol and cigarettes. There was a long black overcoat over her. Her glasses were hanging from her outstretched hand, and her strawberry ginger hair was swept back underneath the couch pillows.

Jane pushed her; no response. She pushed her again, more forcefully. Again, no response.

"Hello?" Jane said. "Hello!" She yelled. The girl stirred. The girl looked up, looked back down and closed her eyes.

"Can I help you?" Jane said, clutching her robe tightly to herself.

"No, I'm fine." The girl replied.

Jane leaned back, her jaw slacked.

"What are you doing here?"

"Roger." The girl mumbled.

"What?" Jane asked.

"Roger." She yawned. "Left me in the car. It's freezing."

"Where did he pick you up?" Jane's face flushed.

"What?" the girl sat up.

"Which club did he pick you up from? I'm going to call you a cab." Jane turned around.

"He didn't pick me up from a club." The girl put her glasses on, running her hand through her hair. "I work at Sterling Cooper."

"You work with him?" She raised her voice.

"Kaye Sharpe." The girl extended her hand.

"You bring my husband home, drunk, at some ungodly hour, and you expect me to shake your hand?" Jane's voice was raised.

"Get over yourself." Kaye retracted her hand. Jane recoiled back, her face becoming bright red. "If I fucked him, why would I sleep in your damn living room." She laughed lightly, still feeling the residual effects of the alcohol.

Jane had no response but instead, clenched her fist and punched the opposing woman square on her face. Kaye fell back in shock, her glasses breaking in half at the bridge. Her lip was cut, and her nose bled slowly. Jane covered her mouth, gasping.

Kaye said nothing.

She pulled the glasses pieces from her face and found her footing once again. She adjusted the large gold signet ring on her right hand and swung at Jane's head. It connected just above Jane's temple and she was knocked back briskly onto the large oaken desk. She slumped down to the floor, clutching her head and screamed loudly. Kaye squatted down beside Jane, spitting blood onto the floor. She grabbed Jane by her chin and dragged her eyes to hers.

"Don't touch me, again." She slapped her across her cheek.

Roger rushed into the room, staggering and looking at Jane.

"What the hell is going on?" He yelled angrily.

"I'm reprimanding your child." Kaye stood up and moved towards Roger.

"Jane what the hell happened."

There were big globules of tears streaking down Jane's face, a large red hand-print visible now on her face.

"I-I-I don't know, she was sleeping there and then I got scared and hit her." She sobbed. Roger ran to her side and sat beside her.

"It's okay, Jane." He rubbed her arms. Kaye left the room, walking into the great hall. She looked around and moved towards the front door.

Roger appeared in the doorway.

"What the hell were you thinking?" He yelled.

"Keep your cat in the kennel." Kaye was observing her face in the mirror. Her lip was growing, and blood was streaked down her chin from her nose.

"That was way out of line." Roger's anger was dissipating.

"Wouldn't have happened if you dropped me off like I asked, and you forgot me in the car."

There was a brief silence while Roger thought.

"I forgot," He hesitated. "I need a drink." Roger turned and walked away. Jane appeared in the doorway, glaring at Kaye who was cleaning herself.

"I want you out of my house." She said, rubbing her cheek.

"Tell Roger he can pick up his car from work." She grabbed the silver keys from the entrance table, and pulled the door open, snatching Roger's fedora and placing it on her head.

"Hey you can—"

Kaye slammed the door and walked out to the Cadillac, covered in a light layer of snow. She sat down in the driver's seat, started the engine and began backing out. Jane came running after her in her robe, clutching it tightly to herself. She was clearly screaming at Kaye but the rumble of the car, and the comforting hum of the radio over road her. Kaye stopped just short of backing into Jane, and as the woman chased her down the drive, Kaye hit the main road and floored it. A plume of white snow and gravel shot into the wake. She raised the volume and rolled the dial until she heard a soft jazz piano playing Autumn Leaves. Her father took her to various hotels during the war as a young girl to hear Kosma play, along with Enoch Light, and this was her favourite song.

Her mind went back to those days, in the cold Connecticut winters, when her father would drive her and her sister to New York for the theatre or some symphony. "There's nothing worse than being uncultured," He told her. Kaye accelerated quickly, leaving Hewlett Bay Park in her rear view. She could feel her heart swing with the chords of the song. Tears came to her eyes, and she began to silently cry. Pulling a cigarette from her clutch, she trembled as she snapped the roller on the lighter a few times before it lit. She inhaled, throwing the lighter aside. The suburb was disappearing behind her, and she was flying down the freeway doing 90. Other cars were falling behind as if they were standing still. She flicked the ashes from her cigarette into the car's ashtray. Traffic condensed once she hit Manhattan, and she slowed down to match speed. Eventually she pulled up out front of the office and parked the car, walking inside, taking the elevator to Sterling Cooper's floor. Don had left the front door unlocked, so she made her way into the office, finding a long orange couch in one of the break rooms. She pulled her coat over her body and threw Roger's fedora onto the table.


A door slammed in the distance. There was hustling around in the main room. Kaye could hear people speaking in a hushed manner. She kept her eyes shut, laying still on the sofa.

"Pete tried to poach John Deere on Saturday."

Ken Cosgrove was speaking. She could hear a woman crying nearby. People were scattering around the office.

"Good morning, Mr. Hooker." She heard a British manicured accent speaking loudly down the hall.

"Did you hear?" Ken walked into the break room, opening the fridge. "Everyone quit. Jumped ship I guess."

"Yeah." Kaye said still holding her eyes shut.

"Hey, your nose is bleeding." Ken said with worry.

"It was yesterday." She replied.

"Are you okay?"Ken had moved towards her, observing her face more closely.

"I'm fine."

"You look like you fell down the stairs."

"Just a cat fight." She finally opened her eyes, realising he was not leaving. "It looks worse than it is."

"That's really rough for you, sorry about your job." Ken moved back, allowing her to sit up.

"Tomorrow is another day."

"Good attitude." He raised his coffee mug to his lips.

"I dunno what I'm gonna do." Ken hummed. "I don't mind working at McCann. It pays the bills."

"In life we often have to do things that are just not our bag." She said.

"Isn't that the truth." He smiled. "I'm going to go find Paul, have a question for him."

"Good luck."

Ken sprang from the room and Kaye stood up, stretching out the kinks formed in her neck because of the lack of pillow, and rolling out her arms. She walked from the smaller break room to the lunch room and opened the fridge, pulling out an apple and a jar of milk. She downed the milk, throwing the jar in the garbage and finished her apple.

"You're still here?" Lane said, appearing behind her. She turned, cleaning the blood from her face at the sink.

"Slept on the couch. Long night."

"Apparently." He paused. "I've just been sacked."

"Shame." Kaye smiled.

"Listen," He walked closer to her, hushing his tone. "We're at the Pierre. Fourth floor, room 465. I'm about to head there now. I'm going to call a cab, we can share."

"I have a car. We'll take that. Do you have your things?"

"Mr. Hooker is dealing with them."

"I'll follow you out." Kaye grabbed her long overcoat and Roger's fedora, placing it on her head.

"Quite an unorthodox hat." Lane commented.

"Then it suits me." She said.

The Cadillac was still sitting out front of the building and she unlocked the door. Once inside, the monster took off towards East 61st, and eventually over to 5th Avenue. They rolled up out front of the Pierre, Lane making pointless small talk during the trip. Kaye parked the car, and they took the elevator silently. They walked down the white-washed halls and knocked at 465. Joan opened the door, smiling at Lane and indifferently looking to Kaye.

"There you are." Pete said. "You're late."

"Can't control when you're fired." Lane laughed.

Kaye sat down on the sofa beside Roger and placed the fedora on his head, and his car keys into his hand.

"Sorry." She said, looking around the room.

"You're lucky you have a contract." Roger, smiling, looked over to Lane. "Hey, throw your shoes out front."

"What?" Peggy asked.

"If you leave your shoes outside here, they will polish them." He said. Don emerged from the bedroom near the back of the hotel room.

"Hello Don." Lane spoke.

"How was your morning?" Don smiled.

"Very productive." He replied.

"Kaye, good morning." Don continued.

"Morning." She replied, looking to him.

"Again," Joan said. "Do not under any circumstances bring clients to this hotel. Use any other hotel in this whole city, except this one."

"We have an announcement to make." Roger said, clasping his hands together, and standing. "Now, I know we all want to stay at the Pierre forever, but we're looking forward with Sterling Cooper and Friends expansion." He moved over and grabbed a drink from the table. "The Maidstone Club last night was fruitful."

Don looked to Kaye, who sat unmoving. He now saw that she looked battered and her glasses were gone. She had that look of timeless beauty, despite the pain. Not like Betty who had that hot beauty that excites every sense, but just that everlasting beauty that accepts a man as he walks into his home, and he never gets bored of that kiss on the cheek. She was still young and foolish.

"Dear Miss Kaye spoke to an old friend of hers, Juan Trippe at the club, and through some smooth talking, we have a pitch at the end of January with Pan Am."

Pete interjected immediately, "Like Pan American Pan Am? The airline?"

Joan smiled, looking over to Lane, Don, and then Roger.

"Kids got talent." Roger raised his glass. "Here's to you Kaye. You promised a whale. You caught the leviathan."

"So, we have a month to throw together everything for the biggest airline in the world?" Pete continued.

"All hands on deck." Kaye quipped.

Don, leaning down raised his glass.

"Our nights are about to get a lot longer."

"And our days too." Lane smiled, picking up a water glass.

"Cheers." Roger said, and those with drinks drank them down.

"Kaye, I want you working with Peggy." Don started. Kaye spun on the spot to face Don. "We'll start this afternoon. Joan, when's that table going to be here."

"The movers said this afternoon." She reefed through some files.

"Why don't we work separately, then come together?" Peggy whined.

"She's your boss, Peggy." Don replied, sternly. "We're all playing nice. We need this, more than anything right now."

"It'll beat the hell out of a hotel room." Harry said, running towards the bedroom.

"Kaye, you're coming with me. We'll be back in a few hours. Peggy, get started."

"I don't even have a table!" She complained.

"Use the coffee table, I don't care, just start."

"I'll call Pan Am." Roger finished another glass and placed it down beside Joan. "Joannie, could you call in?"

"Yes, I suppose." Joan said.

Don motioned to Kaye to walk out. She placed her beige overcoat on and walked beside Don.

"Where are we going?" She said in the hall.

"Grieg's Optical." He replied, calling the elevator.

They rode down to the lobby in silence and walked through the golden front doors. Don's Cadillac was parked south. He opened the door for her, and she slid into the seat. Don followed. They pulled out into traffic, and he began speaking.

"I know you don't say much—"

"Thank you." She said, looking to him intently. He understood. They continued riding in silence.


"Good morning, this is Joan Harris calling from Sterling Cooper Draper Pryce, I'm calling regarding a meeting which our Senior Partner Roger Sterling had with Mr. Trippe last evening. Would he be available?"

"One moment." She said.

There was a moment's silence on the line. The meek secretary put the line through to Trippe's personal phone. The old man picked up.

"Trippe here."

Roger took the receiver from Joan's hand.

"Mr. Trippe, it's Roger Sterling. We met last night at the Maidstone."

"Of course." A brief pause. "What can I do for you?"

"Well, we never got the details of what you wanted from us."

There was another silence.

"Mr. Sterling, I'll be frank. I'm just doing this as a favour to a friend—"

"And we appreciate that." Roger added quickly.

"—Good. As I was saying, it's a favour, so I'm asking you not to be optimistic."

"We don't need optimism, we just need the chance."

"Well—I spoke with the board. They aren't enthusiastic. But they are willing to hear anything that means more business. I have time, as I told Kaye, towards the end of the month. You come to us at Park Avenue and we'll sit in. I suppose you'll have about a half hour."

"I'll have my secretary keep all this down." Roger sat against the desk beside Joan.

"You really need an ace in the bag, Mr. Sterling. I hope you understand that."

"We'll put out all the stops." He smiled through the phone.

"You'll need it. I've got to go. Goodbye." Trippe hung up the receiver, Roger followed.

"So?" Joan implored.

"Well," Roger pulled a cigarette from his case. "I've worked on worse accounts than this will be."

"Oh, Roger." She sighed.

He inhaled on his cigarette. "Give me the odds on us landing this thing." He looked thoughtfully to the ceiling.

"The talent pool is deep and wide." She said, without looking up.

"I suppose." He paused.

"When did we hire Kaye Sharpe?" Joan asked from the blue.

"Friday." Roger continued smoking.

"No, I mean before."

"I don't remember. I don't remember anyone we hire. I hardly remember hiring Don."

"Funny, I don't remember hiring her either."

Roger cocked his head in thought.

"She's smart. Reminds me of you, Joannie."

"I don't like her."

"That's exactly what you'd say about you." Roger said.

"She's arrogant." Joan continued, standing and moving towards one of the sandwiches Trudy brought in. She picked it up and unwrapped it, taking a bite.

"Who isn't?" Roger said.

"Why are you defending her?" Joan asked, innocently.

"I like her." He said, picking up a glass of whiskey. "Let's go for lunch."

"We just got here."

"Let's go for breakfast, what's the difference?" he said, putting on his coat.

"Fine." She moved for her coat. "Pete, look after the children."w


New Years 1963 came uneventfully. A memoriam for Kennedy was held in Rockefeller Square over the weeks following, even though the government mandated mourning period ended, and the cool weather continued to whistle and blow between the tall towers of the bustling city. It was awash with grey most days, and damply cool.

Pete Campbell was struggling to maintain Samsonite but had wrangled the troops to give a decent pitch which was accepted, bringing some mall victory to SCDP, albeit no more cash. Peggy was spread thin as she, Kaye and Don, worked around the clock coming up with ideas. Roger had managed to bring in Tandberg, the electronics manufacturer. It wasn't much, but it was something. Harry was busy building up the framework for the television department, which Bert Cooper saw as the future of the advertisement industry. Joan spent almost all day organising clients, calling clients, setting dinners with client, and turning Room 465 at the Pierre into a real office. The couches had all gone, Don was moved to the second bedroom, there were cubicles in the main room, and much to Roger's chagrin, the bed was taken out of the first bedroom and replaced with Harry's mess of desks and spreadsheets.


New York City

Mid-January 1964

Kaye Sharpe was leaning back in a swivel chair, holding a cigarette to her lips, and looking in the mirror, hung above the fireplace in Room 465 at the Pierre. She had moved her chair out of the cubicle that Joan had created for her, which had barely enough to fit her desk and chair. She sat almost in the middle of the room. The clacking of a typewriter resounded in her head, the reaming of paper, ribbon spooling; somewhere in the distance Harry Crane was on the phone. She exhaled slowly on thick blue smoke, adjusted her black horn-rimmed glasses, and looked down to a newspaper on the small coffee table near the fireplace. Moving over, she picked it up, opened it and began reading.

"Did you do the colouring for the Jai Lai ad?" Peggy leaned out of her cubicle, in front of Kaye.

"I'm just going to multi-layer print it."

"It's cheaper if we just colour it here."

"It's easier if I print it."

"We're trying to be frugal."

"I'll take it out of my own pocket." Kaye flipped the pages of the paper, allowing the cigarette to dangle from her lips. "Have you got anything for Pan Am?"

"I have a few ideas, I'll share them at the meeting."

"What meeting?" Kaye asked.

"We have a meeting in 10 minutes with Don."

"I'll join you. I love bedroom meetings." Roger said, peeping his head over his far cubicle.

"Good morning." Don said, entering and removing his coat. Joan stood up from her desk and took his coat and hat from him.

"Good morning, Mr. Draper." She said, hanging them on a far standing hanger.

"Peggy, Kaye, my office." He strut past them. Roger stood up, following Kaye.

The threesome entered the bedroom, closing the door. Don had a medium-sized desk set up, made of ugly particle board, and an orange tall chair behind it. The room was devoid of anything on the walls and consisted only of a drinks cart.

"I see you have your priorities straight." Roger moved smoothly to the cart and began pouring.

"Where are we on Jai Lai?" He asked, sitting down.

"Printing them off today." Kaye said.

"Good. The pitch is Thursday, at the Roosevelt. How about Pan Am."

Roger leaned against the window, looking down on the street. There was a brief silence.

"I have a few options. Television and print." Peggy said, pulling out a file folder.

"Okay?"

"Harry" Kaye yelled. "Get in here."

Peggy leaned against Don's desk, ruminating on her choices. Harry walked in.

"What?" he said.

"A little boy, he's boarding a Pan Am flight, holding his mother's hand. She's dressed well, not overly well. Her husband is beside her, in a suit, smiling at the stewardess as they enter the plane. The little boy is worried. He seems scared. The stewardess escorts them to their seats, they all sit down. The stewardess notices the boy is worried, bends down, and addresses him. What's wrong, Timmy? She says. I've never flown before. I'm scared. The stewardess smiles. There's nothing to worry about Timmy, you're on the greatest airline in the world, she stands up and the narrator says Pan Am Airlines. The Greatest in the World."

"Not bad." Harry said. "We could rent a cheap set to build a tiny portion of the plane. Wouldn't take much."

"It's reliant on the personal experience of the passenger always being good, and new." Don stood up, pouring himself a drink beside Roger.

"That Pan Am 707 slammed into some town in Maryland last month." Kaye said. "They aren't on good footing with 'safest and greatest' right now."

"Well there you go. It's a good ad, Peggy." Don said, handing her a glass with a small amount of whiskey. "Just not right now."

"Planes crash every year. People still fly." She protested.

"This is Pan Am's first crash in a decade. The last one was in '52. People won't remember 1952. They will remember December 1963." Kaye said.

"I remember '52. Good year for Merlot." Roger said.

"How'd you figure that out?" Harry asked.

"I drank a lot of Merlot."

"I mean about the crash."

"The papers. Big spread in the Times after it happened." Kaye butted her cigarette in Don's crystal ashtray.

"Okay, so what else have you got." Don said.

"Well—that was sort of the big idea. Everything else branches off that." Peggy said.

"Great." Don put down his glass after having a sip. Peggy held hers nervously. "Get back out there and keep going."

"You're not going to ask me?" Kaye said.

"If you had something you would have said it." Don sat down in his chair.

Kaye and Peggy turned, leaving the room.

"We have a lot riding on this race." Roger said, drinking.

"I know." Don replied. "We'll have it."

"I can grease the wheels over there."

"We need the ad. Not more time." Don stood from his seat. "Harry you can go now."

Harry left quietly.

"Joan, can you come in here." Don yelled out the door.

The tall redhead strode into the room sporting a blue dress.

"Yes, Mr. Draper?"

"Call Pan Am, I want to go on a tour of their planes."

"We're going on vacation? I'll start packing. I hear Tahiti is nice this time of year." Roger said.

"Alright, I'll see what I can do." She smiled, and slipped out of the room, closing the door.

"I need them to see what their missing." Don said, pouring more whiskey beside Roger.

"So, you're going to take them to Tahiti?"

"It's not about the destination, it's about the journey." Don slowed as he finished the sentence. He looked down out the window.

"Kaye, get in here." Don yelled.

The young woman walked in, closing the door.

"It's not about the destination, it's about the journey." He repeated, smiling.

"Okay—" Kaye said, waiting for more.

"We show a family, about to leave for vacation. They have their bags packed." He moved towards her. "The kids are complaining, are we there yet? The mother sympathetically smiles, no dear, we haven't even left yet. They are getting on the plane, Pan Am logo in the background. They take their seats, Dad are we there yet? The son asks, his father turns to him, Son, sometimes it's all about the journey, not the destination."

Kaye was writing notes down. She pushed her frames up her nose bridge and looked to Don.

"It fades to black; Pan Am. It's all about the journey." Kaye said, looking only at her notebook.

"Get to work on that with Peggy. We're going to Idlewild - or John F. Kennedy I guess - to see Pan Am today. Joan is organising it."

"Alright." Kaye walked out of the room and out to Peggy. She threw down the notebook on Peggy's desk. She read it over.

"You had this and never shared it?" Peggy questioned.

"Don came up with it."

Peggy sat and read through Kaye's notes.

"It's good. Inviting, realistic."

"We're going to Idlewild to see the planes." Kaye said. "Grab your coat."