Bertram Winkle

All info was provided Bertram Winkle at Jessie Wiki Bertram Winkle is the Ross family's butler. He is disinclined to work and quite sarcastic. He is shown actually doing work, however, only when the Ross parents are visiting. For some unknown reason, Bertram does not show that he wants to be fired.

Personality
Bertram is the Ross family's lazy, sarcastic 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, seem to like Jessie, though he sometimes gives her advice, not knowing his intentions and mistakes 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, like when he tries to help them. When the Ross parents are home he pays extra attention to his job.

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 (Are You Cooler Than a 5th Grader?). In "Romancing the Crone", Bertram asks Mrs. Chesterfield on a date in order for Jessie and Zuri try to get Mrs. Ross's tiara from Mrs. Chesterfield's terrace.

Trivia

 * Out of all the Ross kids, he dislikes Luke the most and likes Zuri the most.
 * He is a hoarder.
 * He wanted to go to Mexico for his Christmas vacation (Christmas Story).
 * Most of his high school classmates got bald and/or went to jail. (One Day Wonders)
 * He wants to be rich (The Princess and the Pea Brain).
 * He went to one of Zuri's tea parties after she got rejected by Emma (Zombie Tea Party 5).
 * He was probably on the wrestling team in high school.
 * He once went out with Mrs. Chesterfield so that Jessie wouldn't lose her job and Zuri wouldn't get in trouble.
 * He has a "Butlers of the World" game card collection (Creepy Connie Comes a Callin')
 * He got hurt while making a banana split, slipped on a banana peel and did the splits and choked on Kenny the Koala's stuffing (Creepy Connie Comes a Callin').
 * He weighs 279 lbs.
 * Despite his size, he is a coward. He even sobs just like the Cowardly Lion from the 1939 film The Wizard of Oz many times in the series, a possible reference to the fact that Kevin Chamberlain once played that same character in the stage version.
 * Mr. 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. (The Princess and the Pea Brain)
 * He searches everyone's room for loose change.
 * His last name is Winkle. (One Day Wonders)
 * He is claustrophobic. (Tempest in a Teacup)