Sidney Glass

"I can grant your wish."

- Sidney to Emma Swan

Sidney Glass is a recurring character on Once Upon a Time. He debuts in the second episode of the first season. He is played by guest star Giancarlo Esposito and is the Storybrooke counterpart of the Magic Mirror.

Sidney Glass was formerly the chief editor of Storybrooke's The Daily Mirror, a newspaper. He now works as a freelance reporter and is a loyal spy for the mayor of the town, Regina Mills.

Season One
Sidney Glass first makes his appearance on The Thing You Love Most. He has been gathering information on the newcomer Emma Swan under the mayor Regina Mills' orders. However, he is unable to get anything from her. Regina threatens him, and he leaves.

Sidney then publishes many articles about Emma's messy past, trying to make the townspeople begin to hate her. However, this tactic is unsuccessful. Some articles on Emma's past include how Henry Mills was born, and that she was drunk when she hit the Storybrooke landmark by the side of the road.

After Sheriff Graham's death, Regina appoints Sidney as the new sheriff. However, Emma challenges this. He makes a speech at the debate that occurs prior to the election, something that was clearly created by Regina. However, due to Emma revealing that the fire at the mayor's office was Mr. Gold's doing, he lost. This caused Regina to fire him from The Daily Mirror.

Many days after the election, Regina has an argument with Emma. After the mayor leaves, Sidney slides into the opposite end of the booth Emma was at and tells her that he can help her expose Regina for who she really is. Emma is skeptical at first, but Sidney gives her a card with his number and leaves.

After Henry's castle is torn down, Emma partners with Sidney. Together, they raid her office and discover that fifty thousand dollars had been stolen from the Storybrooke treasury. Emma also discovers Regina's keys to every house in Storybrooke, but doesn't do anything about it. They also find that she had bought land from Mr. Gold via Storybrooke's money.

However, when they try to expose her at the town meeting, the "house" that Regina was building was actually a modern playground for the children of Storybrooke. Ashamed and embarrassed, Sidney retreats to Granny's Diner in order to have a drink. Emma joins him there, and the two pledge to become allies.

However, the next morning, Sidney is at Regina's office with new photos of Emma and Henry. He had been following the sheriff under Regina's orders. Regina praises him for his good work and tells him to keep it up. He stares at her and has no reply, a sign that he might actually hate Regina, as he had told Emma.

The day after Kathryn Nolan's disappearance, Sidney arrives at the scene of the crime in order to get the scoop on the story because then The Daily Mirror would have to take him back. He offers to get some phone records for Emma, to which she agrees. However, the phone records were actually falsified by Regina in order to incriminate Mary Margaret Blanchard and David Nolan.

At the Miner's Day festival, when Mary Margaret rushes off with Leroy to sell candles door-to-door, Sidney attempts to convince Emma that Mary Margaret is a liable suspect for Kathryn's disappearance and possible murder. However, Emma jumps to Mary Margaret's defense, and that's the end of that.

He brings her the fake phone records, at the top of which is an eight-minute long conversation with David. When Emma tries to defend David, he gives her a liable argument, leaving her stumped. His influence later causes Emma to take David to the station, to the shock of all the townspeople.

After Kathryn Nolan is found alive, Emma confronts him in the diner about having planted a listening device in her office to eavesdrop on her conversations. Sidney tries to play it off, but Emma knows he is still working for Regina. When pressed further, Emma finds out he is in love with Regina, and gives Sidney the ultimatum that he can either go down with Regina or help Emma bring Regina down.

Later, Sidney confesses to having kidnapped and falsified the evidence indicating Kathryn's death in a last ditch attempt to somehow get his old job back. He seemingly confessed at Regina's prompting after Emma indicated she would pursue Regina as the guilty party. Emma doesn't buy his confession, and warns Regina she won't let her have her way.

In the season finale, it is implied that Sidney was imprisoned by Regina in the basement of Storybrooke Hospital, as seen when Jefferson passes a door marked "S. Glass" on his way to release Belle from her cell.

Triva

 * His last name, "Glass", is an allusion to his past life as the Magic Mirror.
 * He often speaks in mirror-related puns and indirectly references his former life as a genie and fortune-teller.
 * He has access to various electronic wiretapping and surveillance equipment which he uses to spy on people for Regina.

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