Rhoda Chesterfield is the main antagonist in JESSIE. She is a rich and selfish woman who is the head of the condo board of the Ross family's apartment. She modeled for magazines where she was called a "Spring Chicken".
She is portrayed by Carolyn Hennesy.
She owns a pet long haired chihuahua called Zeus, who she loves even more than her daughter. She doesn't like reptiles due to the fact that she has a phobia of them and because Mr. Kipling liked the taste of her. She even tried to have Mr. Kipling removed from the building after she found out he was living there; however, when a hawk tried to attack her Chihuahua, Mr. Kipling saved the dog's life by swatting the bird away with his tail. Afterward, she decided to allow Mr. Kipling to stay. She is cruel, spoiled and mean at first, but somewhat softens and is nicer afterwards, she’s known to lie, cheat and backstab to get what she wants (money, wealth, fortune, etc). Out of all the Ross children, she favors Emma, mainly because Emma annoyed her the least. She also calls the Ross Kids and Jessie names. Mrs. Chesterfield briefly loses her fortune however she gains it again soon after. She’s somewhat a flirt and sexually abusive, such as pinching Tony‘s butt numerous times and slapping Bertram’s butt several times.
Rhoda Chesterfield likes Bertram. In the episode "Romancing The Crone", Jessie accidentally drops a diamond tiara belonging to Mrs. Ross onto Mrs. Chesterfield's terrace, Jessie convinces Bertram to ask Mrs. Chesterfield out on a date to retrieve it. Bertram told Mrs. Chesterfield that if she didn’t tell on Jessie that he’d take her out on a real date and she happily agreed.
- The Talented Mr. Kipling
- Are You Cooler Than a 5th Grader?
- Romancing the Crone
- Glue Dunnit: A Sticky Situation
- Ghost Bummers (Dream)
- Between the Swoon and New York City
- No Money, Mo' Problems
- There Goes the Bride
- She enjoys watching The Real Housewives of New York.
- She hates large reptiles, such as Mrs. Kipling. However, since Mrs. Kipling saved her dog's life, she tolerates her presence.
- She has named everyone but Luke different names. Jessie got Bessie, Tressie, Tessie, Essie, Jimmy and Jezebel. Emma got Jemma. Ravi got Rover. Zuri got Zubi, Zippy and Zsa Zsa. Bertram got Bertie.
- Her feelings were fake for her first husband.
- She felt disgusted during her entire second marriage.
- She was happy upon finding out that her third husband was dead.
- She killed her fourth husband.
- Her fifth husband is locked in a storage locker in a restaurant called 'Ezzy's Dine' in New Jersey.
- She and her dog have cheat days, where they allow themselves to eat junk food. Mrs. Chesterfield and Zeus usually binge (eat the food) together.
- She thinks Zuri is very strange and has called her a "strange little girl" multiple times.
- She goes against Jessie's idea of a Lemonade Stand in the lobby.
- She flirts with Bertram and seems to have a crush on him but merely because he saved Zeus' life.
- She hates Indian dragon fire peppers.
- She has a habit of mispronouncing Jessie's name, names include "Bessie", "Nessie", "Essie" or "Tessie".
- Not only does she mispronounce Jessie's name often but she also has a habit of mispronouncing other people's names such as Darla, in Romancing the Crone. She called her, Marla. Although she may do it on purpose to annoy Jessie.
- She wants Jessie to keep Zuri away from her as she seemed strange when Zuri tried to keep Ms. Chesterfield from finding Mr. Kipling.
- Her fear of reptiles is similar to Captain Hook's fear of Tick Tock the Crocodile.
- She's been married twice or more in previous times.
- Jessie broke her tooth in The Talented Mr. Kipling.
- Has called animal control before on Mrs. Kipling.
- Said to be 32 years old (though she is 42 in season 1, 43 in season 2, 44 in season 3 and 45 in season 4).
- She also calls Bertram, "Bertie", as a pet name.
- She isn’t a natural redhead.
- She once said, "When life gives you lemons, do not make lemonade," when the real quote should be "When life gives you lemons, make lemonade."
- She likes Anderson Cooper which makes a reference to CNN (Are You Cooler Than a 5th Grader?).
- She’s very sarcastic saying she was going to suggest going ballroom dancing when Tony said not to move and congratulating Jessie for knowing her own name in Glue Dunnit.
- One of her dreams is diamond rain. (Another one is to see Matt Lauer in the sauna) (Romancing the Crone).
- When she gets Bertram to do something with her she exclaims "SCORE", which could be known as her catchphrase.
- She can no longer cry because her eyes are filled with Botox.
- She has a daughter, who hates her, partially because she likes her dog better than her.
- She likes Emma the most and Zuri the least.
- She really loves her dog, Zeus.
- Her feet are very ticklish. (Romancing the Crone)
- She has two children: Cassandra Chesterfield and Brooks Wentworth
- She considers Zeus and Brooks brothers.
- She changes her last name each time he gets a new husband. (Smith, Holmes, Burge, Wentworth, Chesterfield, Victor)
- Her third husband is deceased. (Four Broke Kids)
- In Four Broke Kids, she’s a skilled trapeze artist just like her portrayer in real life.
- Unlike in Season 1, Season 3, and Season 4 she had only one appearance in Season 2 with it being in "101 Lizards".
- Her first husband was Mr. Burge.
- Her second husband was Mr. Smith.
- Her third husband was Victor.
- Her fourth husband was Mr. Holmes.
- Her fifth husband was Mr. Wentworth and is living in New Jersey.
- Her sixth husband was Mr. Chesterfield.
- Since she slaps Tony and Bertram on the butt several times, it falls in the category of sexual harassment and she should be arrested. She isn’t arrested, however.