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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.


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. It is possible that he cares for her in a brotherly, possibly fatherly way, as he walks Jessie down the aisle on her wedding day. 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 butt 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.


  • Out of all the Ross kids, he dislikes Luke the most and likes Zuri and Ravi 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 has a "Butlers of the World" game card collection (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 Chamberlin once played that same character in the stage version. 
  • Mr. Kipling sometimes gets attached to his legs.
  • He has been beaten up by every one 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 is claustrophobic. (Tempest in a Teacup)
  • He appeared in the Season 2 premiere of Bunk'd. (Griff is in the House)


v - e - d
Jessie logo.png
Jessie • "Halloween Night at the Museum" • "All Howl's Eve"
Main: Jessie PrescottEmma RossLuke RossRavi RossZuri RossBertram Winkle

Recurring: Christina RossMorgan RossMrs. KiplingTony ChiccoliniRhoda ChesterfieldStuart WootenRosieConnie ThompsonAgatha
Others: Col. PrescottJasmine EpsteinDale DavenportBrett SummersVincent LiottaCaleb ShannonDarla ShannonGale GustavoAngela

Season One: "New York, New Nanny" • "The Talented Mr. Kipling" • "Used Karma" • "Zombie Tea Party 5" • "One Day Wonders" • "Zuri's New Old Friend" • "Creepy Connie Comes a Callin'" • "Christmas Story" • "Star Wars" • "Are You Cooler than a 5th Grader?" • "Take the A-Train... I Think?" • "Romancing the Crone" • "The Princess and the Pea Brain" • "World Wide Web of Lies" • "The Kid Whisperer" • "Glue Dunnit: A Sticky Situation" • "Badfellas" • "Beauty and the Beasts" • "Evil Times Two" • "Tempest in a Teacup" • "A Doll's Outhouse" • "We Are So Grounded" • "Creepy Connie's Curtain Call" • "Cattle Calls & Scary Walls" • "Gotcha Day" • "The Secret Life of Mr. Kipling"

Season Two: "The Whining" • "Green-Eyed Monsters" • "Make New Friends, but Hide the Old" • "101 Lizards" • "Trashin' Fashion" • "Nanny in Miami" • "The Trouble with Tessie" • "Say Yes to the Messy Dress" • "Teacher's Pest" • "Jessie's Big Break" • "Pain in the Rear Window" • "Toy Con" • "To Be Me or Not to Be Me" • "Why Do Foils Fall in Love?" • "Kids Don't Wanna Be Shunned" • "All the Knight Moves" • "We Don't Need No Stinkin' Badges" • "Somebunny's in Trouble" • "Punch Dumped Love" • "Quitting Cold Koala" • "Panic Attack Room" • "Throw Momma from the Terrace" • "The Jessie-nator: Grudgement Day" • "Diary of a Mad Newswoman" • "Break-Up and Shape-Up" • "G.I. Jessie"
Season Three: "Ghost Bummers" • "Caught Purple Handed" • "Understudied and Overdone" • "The Blind Date, the Cheapskate, and the Primate" • "Lizard Scales and Wrestling Tales" • "The Rosses Get Real" • "Good Luck Jessie: NYC Christmas" • "Krumping and Crushing" • "Hoedown Showdown" • "Snack Attack" • "Creepy Connie 3: The Creepening" • "Acting with the Frenemy" • "From the White House to Our House" • "Help Not Wanted" • "Where's Zuri?" • "Morning Rush" • "Lights, Camera, Distraction!" • "Spaced Out" • "The Telltale Duck" • "Coffee Talk" • "Between the Swoon and New York City" • "No Money, Mo' Problems" • "The Runaway Bride of Frankenstein" • "There Goes the Bride" • "Ride to Riches" • "Jessie's Aloha Holidays with Parker & Joey"
Season Four: "But Africa is So... Fari!" • "A Close Shave" • "Four Broke Kids" • "Moby and SCOBY" • "Karate Kid-tastrophe" • "Basket Case" • "Capture the Nag" • "What a Steal" • "Driving Miss Crazy" • "Bye Bye Bertie" • "Rossed at Sea" • "Dance, Dance Resolution" • "Someone Has Tou-pay" • "Identity Thieves" • "Katch Kipling" • "The Ghostest with the Mostest" • "The Fear in Our Stars" • "Jessie Goes to Hollywood"