"I'll miss you, too. But, the thing that I would hate more than missing Christmas is knowing that you didn't have a great one. So. Can you promise me that you will have the best Christmas possible? Even if I'm not here?"
― Alisha Reynolds to Sydney in one of her memories
How The Syd Stole Christmas is the first episode in Season 2 of Sydney to the Max. It first aired on December 13, 2019 to 0.40 million viewers.
The memory of her late mother and some long-forgotten advice helps Sydney rediscover her love of Christmas again, a holiday she has avoided ever since her mother passed away.
The episode begins with Sydney and Olive returning from school, Sydney talked about the trip she was going to do with her family for Christmas. But Max appears and gives her the bad news that the trip was not going to happen since the flight was canceled, and since there were no more options, they would have to spend Christmas at home, as they used to do years ago. Sydney seems to oppose that idea. Later, she informs them that she volunteered to give donations to a family in need. Max tells her to come back in time to go buy the Christmas tree. Sydney tells him not to worry and leaves with Olive. Judy and Max notice Sydney's attitude and believe it could be because it would be the first Christmas they would spend at home without her mom. They remember how four years ago Sydney, Max and Alisha came to buy Christmas ornaments and the excitement that Sydney shared with his mother when making the decorations of the house.
Later, Sydney and Olive arrive at the Millers house to deliver the donations, there they meet Carol and her son, Charlie, Sydney talks with them and insists on staying with Olive and helping her with her preparations, although Mrs. Miller had suggested that they should go home.
Later, they return home, Sydney apologizes to Max for not having arrived on time, but in the living room, Max surprises them by showing them the tree he had bought. He is going to buy more lights for the tree. Sydney and Olive are watching the tree, Olive was excited, but Sydney remembers how she spent Christmas Eve with her mother and how they had a similar tree, then she tells Olive that they couldn't have the tree, she says they should give it to her to the Millers. Then, with the help of Iggy they take the tree to the Millers house, Sydney intends to stay there longer, but Olive takes her back to her house.
Later, Sydney returns home, there she tells Max that she gave the tree, Max does not understand why she did that and tries to talk with her about what she felt, Sydney does not want to talk about it, but finally tells him that she acts like this since since her mother passed away they could not celebrate Christmas, then she leaves. Sydney returns to the Millers house. She talked with Mrs. Miller about her son, Charlie, mentioning Sydney to her mother who was a doctor, Mrs. Miller tells her that she knew her, since she had helped her in the births of her children, one of these occurring at Christmas. Sydney remembers that Christmas Eve, when her mother told her that she had to leave and that made her sad, but she felt better when promising that she would have the best Christmas even if her mother wasn't present. Sydney reflects on that and decides to return home. She gets a small tree and arrives at her house with Olive, encouraging Judy and Max to celebrate Christmas Eve. Sydney tells Max that she understood that she owed it to her mother and then makes a joke on him, as she used to do with her mother. In the end, they both hug.
In the Reynolds house, Max and Leo arrive from school and are surprised to see that Judy had put Max's present under the tree, Judy sees them grabbing the present and takes them away, leaving the present in the same place when considering Max wouldn't open it. But as soon as she left, Max grabs the present and opens it, seeing that it is a start-up jacket and getting excited about it. Max thinks he could take the jacket to school to wear it and could return it later. But when he went to school and left his jacket in his locker, it opened and the jacket fell to the ground, being taken by someone. Max and Leo look for the jacket but can't find it. Max was worried Judy would find out. Suddenly, someone knocked on the door of his house, it was Pete, one of his classmates, he returns the jacket and tells him that he picked it up and kept it since he could never have one like that. Max was upset about what he did, but Leo tells him that he was from a needy family, so Max calls Pete back and gives him his jacket. When Leo leaves, Max approaches Judy, he tells her that he took out his present and lost it. Judy, who had watched everything from the door, hugs him telling him he was so grounded.
Despite this being the first episode of Season 2, "Father of the Bribe" was advertised as the Season 2 Premiere.
This is the only Season 2 episode to air in 2019.
Olive is revealed to be Jewish as Sydney says Olive celebrates Hanukkah.
This is the seventh episode to end in the past, though not in 1992.
R&B singer Rihanna, who does the voice of Tip Tucci in the Dreamworks Animation film Home, is mentioned in this episode.
This is the first episode in the series with more than one past history shown.
It can be noticed that pictures of Alisha shown on the wall were removed as the years have gone on in the series.
This is the first episode of the series to have a deep concept to it.
At the end of the episode, it is revealed that Alisha bought Sydney the bass guitar that she uses.
Moral: Don't avoid holidays for the sake of someone not with you anymore.
Starting with this episode, the end credits plays after the last scene of the episode, Disney Channel airings have the credits play during the last scene of the episode but it's moved to the middle of the screen instead of the bottom center, which can possibly be distracting for viewers.
The flashback to the last Christmas with Alisha is set four years ago, however in "Can't Hardly Date," Sydney says Alisha died five years ago.
Sydney says Hanukkah was "two weeks ago" when Hanukkah is actually in the same week of Christmas.
Sydney's Christmas Flashback 🎁 Sydney to the Max Disney Channel