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We open on Simon and Zach coaching models at a photo shoot. Simon asks the male model to step out and for Zach to take his place to show him what he wants. The female model, Carly, tells Zach they went out a month ago but he clearly doesn’t remember and dodges. Simon the coaches Zach and Carly to do weird hand movements then instructs Zach to “twirl her then pull her back and dip her so her dress billows.” Zach does so but then Simon asks Carly to step out and he and Zach dance together.
Zach finds Andrew and another girl in the elevator going up to the office. Andrew notices Zach’s new jacket and Zach tells it was from the photo shoot and that Simon gave it to him “for a job well done.” Zach then tells Andrew that “if I get a jacket, it’s like you get a jacket. We’re a team.” Andrew doesn’t look too sure. The girl tells Zach that the jacket looks great on him and introduces herself as McKayla and Zach introduces himself. As they leave the elevator, Andrew tells Zach that he gets all of the credit because he talks more in meetings. Lauren approaches and asks what’s going on. Zach tells her that Andrew thinks that Simon likes him more than Andrew. Then, Simon loudly hi-fives Zach plus a few more body movements in unison as Andrew and Lauren watch. Then, Andrew politely says hello to Simon and he politely says it back. Then, Sydney appears to tell Simon that “a bunch of ducklings were just delivered to your office.” Simon is happy they’ve arrived and says that they are for his “pro-bono project.” Sydney isn’t happy that they aren’t getting paid and asks Simon what’s going on. He then mentions Arrowhead Pond, which was an “environmental disaster back in the 80s, but that pond is being restored and I’m personally raising these ducks to be its first residents.” Sydney then asks why he specifically is raising the ducks. Simon doesn’t want to give her a straight answer.
Simon is playing with the ducks in a tree in his office even though Sydney reminds him that ducks live in ponds not trees. Simon replies that since they don’t have a pond, “we’ll have to make do.” Sydney then asks Simon if he looked over her “coffee campaign.” He tells her that it was brilliant and she reminds him that he told her he would “tweak it.” Then, Simon advises her to “start again from scratch. There’s always room to aim higher.” He then tells Sydney, “There’s magic in you. I knew it from the moment you were born.” Sydney insists that the campaign works but Simon still tries to change her mind. “It’s safe. The best things in life come from not being safe,” Simon replies about the campaign, which Sydney still insists is good. Simon thinks it’s a “lost cause” then says he has to finish his “Crest campaign and chop up some worms my ducks.”
Zach pitches Simon his idea for the Crest campaign as Andrew looks on as he merely swaps out the storyboards. Simon loves Zach’s pitch and praises him. Zach then tells Simon that a lot of the pitch was Andrew’s idea but Andrew says, “Let’s not do this.” Simon’s confused thinking he said they both did a great job but Zach corrects him that he only praised him. Zach goes on to tell Simon that he thinks Andrew is upset because he got a jacket from the shoot despite Zach’s explanation of how “me sleeping with the girl who liked the jacket is going to be a victory for both of us.” Andrew replies that he doesn’t see that and tells Simon that he’s fine but Simon insists that he isn’t, how he knew both of them worked on the pitch and says that Zach talks more in the meetings. Andrew agrees and Simon says that he “should know better. A boss can’t be doing this. He can’t play favorites. I’m gonna make an effort to be a little more fair. You know, spread the love around.” Simon then tells Zach to give Andrew the jacket “because words without actions are meaningless.” Andrew then says that it’s his first leather jacket and it feels great. But, then Simon says that the jacket looks better on Zach and has Andrew give it back to him. Andrew leaves as Simon and Zach tell him that they will find him something.
Sydney is pitching a “targeted bus-and-billboard campaign that we project increased growth in public awareness for Windy City Coffee over the next five years.” She then asks what Windy City Coffee reps think. A member of the group replies, “I guess we were hoping for a little more…” Another member says that they want to “edge up our brand a bit.” Sydney says that “increased sales growth is exciting. What’s edgy is increased market share.” Sydney then asks Lauren what she thinks. Lauren replies that she’s just an assistant “but would sleep with a Windy City Coffee drinker based on the strength of this targeted bus-and-billboard campaign.” Simon then suggests “a spectacular,” but Sydney insists that the Windy City Coffee reps “don’t want a spectacular.” Simon then agrees that “it’s too big, too exciting,” but one the reps replies that they want “big and exciting and asks what a ‘spectacular’ is.’” Sydney explains that it’s “media event designed to get attention like when Red Bull parachuted that guy from outer space.” The reps love the idea and Simon tells them that Sydney’s “spectacular will be even better than Red Bull’s. It’ll be stunning, stupendous, extraordinary.” The reps love it though Sydney reminds them that they haven’t pitched a specific idea yet. They don’t care, they just want her to make it happen.
Sydney then barges into Simon’s office while he’s feeding the birds in a makeshift pond and yells at him for promising the Windy City Coffee reps that she can deliver “a spectacular.” Sydney then reminds Simon that she doesn’t “do big. I do steady. I do dependable. I’m not you.” Simon then replies that, “the apple doesn’t fall from the tree.”
At the Arrowhead Pond Rehabilitation Project, Simon tells Zach that he wants to make it up to Andrew. He suggests taking Andrew to a Bulls game, but Zach replies that he thought the “Bulls games were our thing.” Simon agrees and asks Zach why he had to look so good in that leather jacket. Zach apologizes. Simon then suggests to Zach about letting Andrew help him with his duck-raising project. “I was looking for backup. I was hoping you would do it.” Zach then asks what that would entail and Simon replies, “Cage cleaning, bottle feeding and this thing called ‘venting,’ where you use a tiny little brush to clean out the duck’s anus.’” Zach then tells Simon to let Andrew help him with the ducks.
Simon and Zach return to the office to find a disheveled Sydney telling them she stayed up all night but came up with an idea for “the spectacular.” “It’s simple but it’s big,” Sydney tells Simon, Zach and Lauren. She then shows them an “optical illusion that sets a pipe from the cup all the way into the carafe that’s hidden by the falling coffee and it’s three stories tall.” Everyone loves it and then Sydney mentions that Andrew did the illusion. Simon then says that he’s about to be rewarded.
We see Andrew ‘venting’ the ducks as Simon watches and coaches him on how to do it right. Then, Zach comes in and asks them if they want to have lunch. Andrew says he isn’t hungry (can you blame him, LOL!) Andrew then tells Simon that he appreciates that he’s trying to do something nice for him but he doesn’t get “this specific thing.” Simon then tells him that the whole Pond restoration project isn’t just a tax-write off and goes on to say how his father used to take Simon there fishing and how he hoped to take his grandson fishing there one day if Sydney “could ever sustain a relationship.” Andrew then sees that the project is important to Simon and Simon replies, “it’s the most important assignment I could give anyone.” Simon then tells Zach that he won’t be going to lunch either because he and Andrew have important matters to tend to. Zach looks a bit disappointed.
We then see Simon and Andrew exit the elevator followed by the ducks as Zach and Lauren watch. The two of them have fun with the ducks all over the office.
Simon and Sydney are at Daley Plaza for the unveiling of the Windy City Coffee spectacular as Andrew and Zach look on. The crowd and reps look pleased as free coffee is being given to the crowd. Simon then tells Sydney how proud he is of her. Zach hears chirping and asks Andrew if he brought a duck with him. At first, Andrew denies it but that says one duck as “separation anxiety.” Then, it starts to rain and get windy. Then, someone yells, “It’s raining coffee!” and everybody runs! Sydney screams at the crowd to “grab a free scone while you’re fleeing.” Meanwhile, the Windy City Coffee reps look disapprovingly at Simon and Sydney.
A news reporter is calling “the Windy City Coffee spectacular,” the “drying cleaning bill of all dry cleaning bills… and a spectacular failure.” Sydney thinks she’s now a “supervillain” for destroying a whole city block. Andrew tells her that “No one could have anticipated this. There was an unusual amount of wind.” Sydney thanks him for saying that and then Andrew moves to feed the duck but Zach says that he wants to. Andrew declines Zach’s help saying that the ducks’ are “his gig” and Simon agrees, says Andrew has “proven himself and ducks have now imprinted on him, so they think he’s their mother.” Andrew then asks to speak to Zach alone and calls Zach on for being jealous of the time he’s spending with Simon. Zach insists that he isn’t jealous though he clearly is. Andrew then says that jealousy is an emotion that Zach doesn’t have. Andrew then asks Zach how his “buddying around with Simon today makes you feel?” Zach admits that he doesn’t like it and Andrew eggs him on saying that Zach wishes “roles were reversed.” Zach admits that he does and Andrew eggs him on more saying that he has “an emptiness in your stomach, and that, my friend, is jealousy.” Zach then asks Andrew if he can hold the duck. Andrew says that he can’t and walks away.
Sydney and Simon get out of the office elevator as Simon tells Sydney that he “tried.” Sydney replies, “Yeah, I tried and I failed. I told you I’m not you.” Simon then tells Sydney that she doesn’t see his “imperfections.” He goes on to say that some of his big ideas haven’t worked and how he’s had “spectacular failures too.” He then confesses that the Arrowhead Pond disaster was his fault. He explains that a “spectacular” was planned and the sponsor was Pop Rocks. “I poured tons and tons of that stuff into that pond. I was hoping for maybe a little fizzing, a little crackling but no. It was a pink eruption. It was like a Pop Rocks Pompeii. It was my PopRocklypse Now. I remember seeing kids covered in pink, crying.” He then says that he knows failure. Sydney then thanks him. Lauren then says they got another email from the Windy City people and they aren’t happy. Sydney says that it’s okay and they’re going to figure out how to fix it. Simon then screams that he believes in her. Then, Lauren points a news clip of “the spectacular’s” failure and the news caster saying that “it was like something out of a horror movie.” Then, Sydney gets an idea.
Simon and Sydney then pitch a black-and-white scene of the “spectacular” like a horror movie to the Windy City Coffee reps. “The attack of the killer coffee,” Simon says as the crowd screams and runs for cover with old-fashioned horror movie blurbs covering the screen then Simon says, “Windy City Coffee. Dangerously good!” The reps love it.
Simon, Lauren, Andrew and a bunch of reporters are at Arrowhead Pond waiting for Simon to unveil the newly restored pond. Andrew doesn’t want to release the ducks saying they’re “city ducks,” but Simon tells him that he has to. Andrew and Simon both say goodbye to the ducks and tell them how much they will miss them. Simon then addresses the press about the project’s completion. Sydney watches proudly as Simon tells the press how the pond’s been restored. “Today is proof of what happens when you dare to dream big but work small,” Simon says. He then says he was unsure they would succeed but has learned “there’s no shame in failing. The only shame is not giving things your best shot.” Everyone applauds and then Simon tells Andrew to “release the quackens.” Andrew whispers to the ducks that he will visit them every Sunday before releasing them, but the ducks won’t go. Then, Simon has an idea. Andrew gets in the pond and the ducks follow as the press, Simon, Lauren, Sydney and Zach watch. Andrew then asks Simon if he’s proud of him and Simon says that he is.