Jonathan Kraskell

Jonathan Kraskell (born 1954) is Charlotte's executive assistant/lackey at work. He is rarely seen but is heard and mentioned constantly by Charlotte as she's almost always seen talking to him on her phone. He follows her words faithfully, often too much at one time in "Let Them Eat Cake", when Charlotte compliments Angelica on how beautiful she is. Jonathan asks if she meant him, when she then clarifies that she was talking to Angelica, he then asks "What about me?". To which Charlotte answers a bit annoyed but mostly baffled, "I'm sure you look nice too". Another example would be in "Looking For Jack", when Charlotte tells Tommy to say "Bye, bye Mommy". Jonathan repeats what she says, thinking she meant him. Jonathan is normally seen as a meek, but also fast talking assistant to Charlotte. If anything she asks for, he rushes to get it. While it would appear that he has nothing against Charlotte, it’s hinted he's not too fond of her daughter. In "Mommy's Little Assets" when Charlotte has to bring Tommy and Angelica to work, its hinted that Jonathan may have to watched or seen Angelica at work. While he is happy when Charlotte first introduces Tommy to him, he has a look of terror when he sees Angelica, saying "You brought her?". To which Angelica grins, saying "I told you I'd be BACK".

At the end of the episode, he's fired by Charlotte for losing Angelica and Tommy. But he's given his job back after he brings Famous Ethel to Charlotte, who announces she'll sell to her company and is given a promotion, to which Jonathan thinks she means Vice President. But he finds to his disbelief that he's in charge of the new daycare for the working parents of her company and was left with Tommy and Angelica to watch to start with, as Charlotte and Drew go out to eat with Famous Ethel.

For the most part, Jonathan seems fairly loyal to Charlotte, but he's also got tendencies of being a "backstabber." An example would be in "Moving Away", when Charlotte was expected to get a new position, she angrily finds out at the end that Jonathan had been given the job. However, for some reason, he was seen working back for her again, most likely he either got fired or quit. In "Jonathan Babysits" tired of feeling degraded by Charlotte and being left with Angelica again, Jonathan decides to rummage through Charlotte's home to find something to blackmail her. For that matter anything that can he find on Charlotte, to teach her a lesson for what he's gone through. He eventually finds an embarrassing video tape of Charlotte when she just woke up in the morning. However, before he has any plans to do so, Tommy and Chuckie, unintentionally get his way of escaping Charlotte's house. When Charlotte finds Jonathan and the babies outside, he presents her the video tape that he found. However, Charlotte ends up being impressed with the way Jonathan stands up to her and rewards him for it--she also punishes Angelica by making her clean up the babies' mess.

In the 2021 series, Jonathan is a Hispanic character who plays a bigger role.

All Grown Up!
Jonathan's mentioned numerous times in the spin-off series, but his only physical appearance was in the fourth season episode, "Lost at Sea", in which the company that he and Charlotte worked for re-organized, and Charlotte lost her CEO-position. Jonathan became the new CEO and subsequently fired Charlotte from the company.

Trivia

 * Some of the babies refer to him as "Donovan."
 * When we see Jonathan for the first time in "Mommy's Little Assets", his skin is an unusual purple color. In later appearances beginning with "Jonathan Babysits", his skin changes to a light brown. In "Angelica's Assistant", his skin becomes more lighter brown. He is completely white and Hispanic in the 2021 series.
 * Jonathan was voiced by the late Rene Auberjonois in his first appearance. However, in all subsequent episodes of the 1991 series, he is voiced by Dan Castellaneta who is best known for voicing Homer Simpson from The Simpsons (Tress MacNeille who plays Charlotte Pickles, plays various regular characters on The Simpsons), Earthworm Jim in the animated series of the same name, and Arnold's Grandpa Phil from Hey Arnold!.
 * Jonathan hates Angelica, because she's caused him a lot of trouble.
 * It is assumed that Jonathan has knowledge or was a part of all the shady and unethical practices/deals Mega Corp has done during Charlotte's tenure as CEO.