Mrs. 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. S model for magazines where she was called a "Spring Chicken".
She is portrayed by Carolyn Hennesy.
She owns a pet 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, bratty, spoiled, and mean at first, but somewhat softens and is nicer afterwards. 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 Chestergield briefly loses her fortune however she gains it again soon after.
- The Talented Mr. Kipling (First appearance)
- Are You Cooler Than a 5th Grader?
- Romancing the Crone
- Glue Dunnit: A Sticky Situation
- Tempest in a Teacup (Mentioned only)
- Gotcha Day (Mentioned only)
- Ghost Bummers (Dream)
- Caught Purple Handed (Mentioned only)
- Between the Swoon and New York City
- No Money, Mo' Problems
- The Runaway Bride of Frankenstein (Mentioned only)
- 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 and her dog have cheat days, where they allow themselves to eat junk food. Ms. 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 most likely older).
- She also calls Bertram, "Bertie", as a pet name.
- She is not a natural redhead.
- She has no feelings for her first husband.
- 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 is 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 know as her catchphrase.
- She can no longer cry because her eyes are filled with Botox.
- She has a daughter, who dislikes her, partially becauses she likes her dog better than her.
- She likes Emma the most and Zuri the least.
- She really loves her pet
- Her feet are 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.
- Her third husband is deceased. (Four Broke Kids)
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 on a date to retrieve it.