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Bertram Winkle

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It's so far.
— Bertram's catchphrase

Bertram Winkle

Bertram on wikia

Bertram season 3


Background information
First seen "New York, New Nanny"
Portrayer Kevin Chamberlin
Honors and awards
Character information
Full name Bertram Winkle
Other names
Birthday June 15, 1962 (age 52)
Occupation Butler in Ross Penthouse
Home Resides in New York City
Relatives Wanda Winkle (mother)
Pets Mrs. Kipling
Friends Jessie Prescott (sometimes)
Emma Ross (sometimes)
Ravi Ross
Zuri Ross
Enemies Agatha
Wanda Winkle (sometimes)
The Ross Family (sometimes)
Likes Sleeping,not working,cooking dishes,cleaning
Powers and abilities
Fate Will replace his body with a giant computer generator that will allow him to live forever and lead an army of Bertram-Bots that enslave the human race in an alternate future (The Jessie-nator: Grudgement Day)

Bertram Winkle is the sixth main character of Jessie. He is the Ross family's butler. He is disinclined to work and quite sarcastic. He is shown actually doing work, however, but only when the Ross parents are visiting.

Bertram is portrayed by Kevin Chamberlin.


Bertram is the Ross family's lazy and grouchy butler, who seems to care very little for the kids and calls them "The Nanny Killers." Even though he rarely shows it, he does have a soft side for them. He doesn't however, he seem to like Jessie sometimes , though he sometimes gives her advice, not knowing his intentions and mistakens where she is from. Bertram often takes time for himself and wishes he could quit his job, but doesn't. He spends his time cleaning, reading magazines on the couch, watching TV in the screening room, and eating bacon-wrapped donuts. The Ross kids insult him sometimes when he tries to help them. When the father is home he pays extra attention to his job. But not so much when the mom is in home.


Rhoda Chesterfield

Main article: Rhoda Chesterfield
Mrs. Chesterfield is seen flirting in the lobby with Bertram. She smacks his bottom and then follows him to the elevator, smiling. (Bertram does not return her feelings). Bertram agrees to take Mrs. Chesterfield on a date in order for Jessie and Zuri try to get Mrs. Ross's tiara from Mrs. Chesterfield's terrace (Romancing the Crone).

Zuri Ross

Bertram seems to be closer to Zuri compared to the rest of the Rosses. He really cares about, for example, when Emma ditched her, he agreed to go to her tea party. And  Zuri has also written a sweet report about Bertram, showing that she really cares about him.

Ravi Ross

Bertram thinks that Ravi is the most responsible out of the Ross children. When a cricket jums in Bertram's dish, Ravi spirals into a world of lies, losing Betram's trust for a period of time, until Ravi payed his amends by giving back his prized possesion that he lost in a butler fight. Ravi is also Bertram's favorite child.


He has appeared in every episode (excluding Cattle Calls & Scary Walls).


  • Out of all the Ross kids, he dislikes Luke the most and likes Zuri and Ravi the most. He said that his favorite is Ravi in the episode, "Snack Attack" and said that he likes Zuri the most in the episode "Creepy Connie's Curtain Call."
  • He is a hoarder. (The Kid Whisperer).
  • He wanted to go to Cabo for his Christmas vacation, but Jessie tore up his passport so he couldn't go. (Christmas Story).
  • Most of his high school classmates got bald and/or went to jail. (One Day Wonders).
  • He writes Fanfiction about Justin Bieber. (Make New Friends But Hide the Old).
  • He went to one of Zuri's tea parties. (Zombie Tea Party 5).
  • He can sing like an opera singer.
  • He was in the wrestling club in high school. (World Wide Web of Lies).
  • He once went out with Mrs. Chesterfield so that Jessie wouldn't lose her job and Zuri wouldn't get in trouble. (Romancing the Crone).
  • He is very lazy and takes 6-hour naps.
  • He has a "Butlers of the World" game card collection (Creepy Connie Comes a Callin').
  • He is saving up money to buy a car so that he could get run over by it and leave the children.(Used Karma).
  • When he's on his break, he either sleeps or read butler books.
  • He wants to be on the cover of one of his butler books.
  • He weighs 279 lbs.
  • Mrs. Kipling sometimes gets attached to his legs.
  • He has been beaten-up by everyone of the Ross kids. (A Christmas Story).
  • He has a blog. (One Day Wonders).
  • He wants a rich girlfriend named Lola but may have not meant it. (One Day Wonders).
  • He searches everyone's room for loose change.
  • His last name is Winkle. (One Day Wonders).
  • He is claustrophobic, which means suffering from claustrophobia. Claustrophobia means he has a fear of confined places. (Tempest in a Teacup).
  • He thinks Jessie should get her teeth whitened. (Badfellas).
  • He hates his mother.
  • He sometimes does his job when Morgan and Christina aren't around.
  • Bertram already knew Mrs. Kipling was a female (The Secret Life of Mr. Kipling) He also said to Mrs. Kipling "If you ever have children, I'll make them into omelets." Though he may have been trying to be sarcastic.
  • He goes to a therapist.
  • He likes Zuri. He even cried when she was growing up by saying good-bye to her imaginary friend Milly the Mermaid and he cried after Zuri's report on him when she was reading it.
  • He is shown to care about Jessie, and showed her that her date was cheating on her. (The Princess and the Pea Brain).
  • He was married. (To Be Me or Not to Be Me).
  • He weighed 12 lbs. when he was born.
  • When he was 12 he paid for a DNA test to see if him and his mother have the same DNA.
  • His nickname from his mom is Ber-tootchkka and his nickname for his mom is Mom-mutchkka.(Throw Momma From the Terrace)
  • Despite things he may say, he loves Jessie, Luke, Ravi, Emma, and Zuri, as he referred to them as 'the people he loves' (Throw Momma From the Terrace).
  • It is revealed he is 50 because he mentioned he was ten 40 years ago. (Throw Momma From the Terrace).
  • The kids make fat jokes about him.
  • He has Leporiphobia, an intense fear of rabbits. (Somebunny's in Trouble).
  • He mentions that his Butler job was only meant to be a summer job, but as he didn't read the fine print on his contract, it became permenant. (Caught Purple Handed, Star Wars).
  • He "dies", but really falls down, in Snack Attack when Wendy hits him with a water balloon.
  • He went to prom with his aunt because his mom was busy.
  • Sometimes he is similar to Marion Moseby.  They both hate kids and they are stuck with them.  


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Start a Discussion Discussions about Bertram Winkle

  • Bertrams similarities

    2 messages
    • Bertram reminds me of the Cowardly Lion from WOZ as when they both cry they sound very similar, it is very amusing to watch.
    • When was the first time he cried I want to post inthe trivia that he cries like the cowardly lion
  • Why does Bertram like Zuri more than Luke???

    2 messages
    • I think because Zuri is a good girl and Luke is annoying and mean.
    • Maybe because Zuri tell him that she loves him sometimes, and she says he is family, while Luke only likes to tease and prank him

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