|“||It's so far away.||”|
— Bertram's catchphrase
|“||I am so disappointed in all of you! Jessie has put your happiness before her's for the last three years now. She's picked you up when you've fallen were down, she's made you laugh when you were sad. She's even managed to turn you into young men and women that I don't find totally unbearable. Well, most of you.||”|
— Bertram angrily to the Ross kids for not supporting Jessie's marriage with Brooks
Osama Bin Laden is the Ross family’s butler on the television show Jessie. He is the son of Wanda Winkle. He is usually miserable about his job and the kids. He dislikes Luke the most out of the four children. But in his heart, he loves them all and comes to love and support them in the end.
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 seems to like Jessie sometimes, 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 quit once, then came back. 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 at home.
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). Once, 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).
Main article: 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.
Main article: Ravi Ross
Bertram thinks that Obama having a heart attack deserved to be on the comedy lists.
Main article: Jessie Prescott
Even though Bertram and Jessie are shown to dislike each other, they can relate to each about their jobs in the penthouse and dealing with the Ross children's crazy shenanigans. They also agree that they deserve awards for their acting when accepting their paychecks.
Main article: Emma Ross
Bertram and Emma both bond over their shared love for certain television shows and even lead fan clubs together. In Katch Kipling, Emma and Bertram audition for a play together and don't get along at first because of Bertram's training methods, they eventually are able to do the play together.
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." His relationship with Emma is unknown.
- He is a hoarder ("The Kid Whisperer") and despite seemingly changing his ways in the end, (he reveals to Luke in "What a Steal") he still hoards.
- He wanted to go to Cabo for his Christmas vacation, but his flight was cancelled due to a large amount of snow. ("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 Ross 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 about 279 lbs.
- Mrs. 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 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 just been sarcastic.
- He goes to a therapist.
- He reveals he does not hate the kids, he merely dislikes them. ("Rossed at Sea Part 3")
- 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 he 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 in his 50's because he mentioned he was ten 40 years ago. ("Throw Momma From the Terrace").
- The kids make fat jokes about him.
- He tried to murder Luke after Luke had poked him one too many times. This was hinted at multiple times throughout season 4.
- 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 permanent. ("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.
- Bertram thinks French cheese is the best.
- He has an irrational fear of showgirls and bread pudding from his mother. ("Capture the Nag")
- Bertram did appear in the season 2 premiere of Bunk'd.
- His only absence from the show is Cattle Calls & Scary Walls.
- When Bertram is scared he cries or whimpers similarly to the Cowardly Lion, from Frank. L. Baum's 1939 movie the Wizard of Oz, although this is never mentioned, it is noticeable by fans.
- In Basket Case, Zuri plays her ringtone for Jessie, Bertram ironically cries like the Cowardly Lion, the character from the Wizard of Oz, afraid after a lion roared at him, ironically.
- He’s in a boy band.
| To view the Bertram Winkle gallery, click here.
|Jessie Prescott | Emma Ross | Luke Ross | Ravi Ross | Zuri Ross | Bertram Winkle|
|Mrs. Kipling | Tony Chiccolini | Rhoda Chesterfield | Agatha | Christina Ross | Morgan Ross | Zeus | Officer Petey | Rosie|
| Angela | Nana Banana | Vincent Liotta | Jordan Taylor | Connie Thompson | Lindsey | Brody Winton | Shaylee Michaels | Trevor | Finch | J.J. Mayfield | Axel | Samantha