May 25, 1965 - the highly anticipated boxing rematch between Muhammed Ali (then Cassius Clay) and Sunny Liston, so Sterling Cooper Draper Pryce will be watching it in the closed circuit theatre.
With Ken Cosgrove back with the boys (presumably bringing with him Mountain Dew), and the recent hiring of the green 24-year old Danny Siegel, the office is buzzing about the fight. Don Draper takes his single ticket and throws down $100 on Liston. Not ready to wisk away to the fight, Draper calls the Sampsonite "team" into his office while asking Mrs. Blankenship to schedule a dinner somewhere else in avoidance of the young executives.
"I don't know why everybody cares so much about it. If I wanted to see two negroes fight, I'd throw a dollar bill out my window." - Ida Blankenship
The Sampsonite Crew led by Peggy Olsen moves aside the furniture in Draper's office and then begins in on their pitch - two unknown football players yielding competitor name brand suitcases charge toward the charming Joe Namath blocked by a beautiful girl yielding the Sampsonite suitcase, but they are no match for the strength of the Sampsonite, and Joe walks away with the girl. They through out tag lines along the way, including "Touchdown Sampsonite!" and "Sampsonite, it's tough." Unsurprisingly, Don is not jazzed, "I don't like Joe Namath, he hasn't even played in a professional game yet." When Peggy responds to Don's criticism, he asks the rest to leave and harshly critizes her work, calling it a "failure."
Peggy returns to her office to a bouqet of pink roses and a card. It's Peggy's 26th birthday. The sender of the card... is none other than Duck Phillips. With the flowers is a small gift - a business card saying "Phillips-Olsen" listing Peggy Olsen as Creative Director. Peggy's happiness is quickly gone as she unties the situation; that Duck had been fired from his other job, he is working from home, and that he is drinking heavily. Duck sells himself to Peggy, and the line between business and emotion blend as he falls into a stuper, confessing his need to be with her again, alluding to prior primal rendeavous.
"... Stephanie from California, no last name, she says it's urgent." Mrs. Blankenship delivers the message to Draper. He struggles, but can't call her back in fear of the upsetting news, so he pours himself a drink. Roger Sterling barges into Draper's office and announces that Freddy Rumpson and Cal Rutlidge from Ponds would be joining them for dinner and the fight, meaning they would have to stunt their overt alcoholism for the evening. Draper manages to duck his way out of the fight entirely, and sets down for his own fight against calling Stephanie back.
Joan Holloway, too, is dealing with her own issues. When the Sampsonite team leaves the common area messy, Joan bangs on her window and charges out to the fleeing men. "Even though I don't get paid as much as one, I am not a janitor," replies Joey Baird, who shrugs and walks away leaving the other two men to give in to Joan's stern request.
Peggy runs into Trudy Campbell in the women's bathroom. They joke about the idiosyncrasies of pregnancy, with Peggy knowing exactly what Trudy is going through. Pete Campbell sees the two exit the bathroom together and the confusion freezes him.
With glass in hand, leaning back in his chair, Don Draper asks Peggy to update him on the creative for Sampsonite, and despite informing him that she had plans, she succumbs and heads back to her office for the stills. Again, Draper tears her work apart and unleashes a verbal tiraid on her. Back to work. As the night progress, their work remains fruitless. Don sidesteps the work into a momentary monologue on his perspective of the fight, the flashy Ali against the methodical Liston, then immediately returns to work, nixing yet another of Peggy's ideas.
Waiting at the restaurant is Peggy's boyfriend, Mark. It is shortly revealed that he is not there alone, but the rest of Peggy's family is there to surprise her. He is clearly uncomfortable. After their second phone conversation, he spills the beans about the surprise dinner to her.
When Peggy tries to leave again, staring straight into the lion's den that is an intoxicated Don Draper, she tells him that she ruined her boyfriend's birthday dinner plans, and Draper goes on the defensive, turning the situation back into a passive-aggressive tactic employed by Peggy. He guilt trips her again, and after storming out of the office Peggy, once again, gives in to Draper. She calls and cancels the dinner, resulting in an outburst by her family and Mark ending their relationship. Once again, we see a little Draper coming out in Peggy Olsen.
But Peggy is determined to turn the downswing into an upswing. Filling herself a drink at Draper's bar, the two butt heads again (in what is one of the most heated scenes in the history of Mad Men.) They yell back and forth, each demanding respect the other doesn't openly give. After taking all she can handle of the liquor soaked assault, Peggy runs off crying.
Peggy: "... you never said 'Thank You!'"
Don: "That's what the money's for!"
While Don feebly tries to narrate his own ideas, he changes the ribbon on his tape recorder to discover Roger Sterling's narrations for his autobiography. It contains ranting and raving about Ida Blankenship days of promiscuity and Bertrand Cooper's lack of testicles. After a chuckle, Draper, displaying a hint of compassion, invites Peggy to share her worries with him. Clearly intoxicated, Draper softens up on her, and invites her out to the "birthday dinner" with all the glamour of a brightly lit diner and a painting of the Parthenon with a roach in it.
Peggy finally pulls something truthful of out Don - the truth about his parents and how they died. (Draper must be bombed.) Relocating to a bar to listen to the fight, Don and Peggy get personal. She tells him about the others believing she slept with him to get the job, and he plays it off and compliments her, "You're a beautiful girl, Peggy." They talk about Peggy's pregnancy, and how he was the only one who visited her in the hospital.
Liston loses the fight. "The fix is in."
The booze finally catches up to Draper. On his knees, in his suit, he vomits vehemenently into the toilet, while Peggy watches on in semi-amusement. There's movement in the office outside the bathroom door, and somebody calls out for Peggy. It is Duck, and he is drunkenly stumbling around in the Sterling Cooper Draper Pryce office. When Peggy finds him, his pants are around his ankles and he is attempting to "leave Draper a little present" while squatting over a white leather chair in Roger Sterling's office. Peggy talks him out of it, but then things turn lush as he confesses his love to her and asks why she didn't answer her phone.
Just then Draper emerges from the bathroom and confronts Duck. Duck turns sour, insinuating that Peggy had "gone back to Draper" and calls her "a whore." Draper charges forward trying to hit Duck, and after a fair amount of grappling, Duck comes out on top holding his fist in the air. In the weakest of moments, we see Draper turn his head and whisper "uncle." Draper defended Peggy's honor and lost.
Beat up in his dark office, Draper falls asleep on Peggy's lap. Don wakes to the sounds of stepping in the hallway, and opens his eyes to see the spirit of Anna standing in his office in a dress holding a suitcase. She looks around, smiles, and then walks away.
The following morning, he makes the dreaded phone call. "She's gone," Stephanie tells Draper. "I know," he responds painfully. Anna's final details break down Draper's facade one piece at a time, until he hangs up the phone and loses control, openly weeping. Peggy is there to witness the goliath fall.
"Somebody very important to me died... the only person in the world who ever really knew me."
Peggy sleeps in her office and is annoyingly awoken by the rest of the Sampsonite team. When Peggy goes back to Draper's office, he is back to the dapper Draper we're used to, tie clip and hair perfected combed. He calls Peggy over to the Sampsonite art he came up with - the recreation of the iconic Ali/Liston 2 image, with the Sampsonite standing victorious.
In a moment which we feared that Don may have learned nothing, we are surprised to see Don takes Peggy's hand and squeeze it. They look at each other, and Peggy smiles back, accepting the gift she had been given. And like that, "go home, shower, come back, and give me ten taglines."
Basically, everybody's got baggage.