Montgomery Whittaker-Dowd is Whit's grandson and a minor character in Adventures in Odyssey. Monty first appeared in the Family Portraits two-parter #17: “A Member of the Family, Part 1”. He later appeared in late 1989 and early 1990 along with his sister, Jenny. Due to his parents' divorce, Monty's surname was changed to Whittaker.
Monty took a hiatus and didn't make an appearance until 2011 in Album 53: The Green Ring Conspiracy, where it was revealed that he joined the Secret Service as an agent.
When Monty was young, he came to Odyssey to stay with Whit while his mother was at a convention. Whit helped Monty become more of a gentleman while he was staying there. He also had to spank Monty because he stole money from the cash register at Whit's End. Monty and Whit soon began having fun; Monty even helped the Odyssey Coyotes win the championship, and was at the victory party when his mother showed up to take him home. She and Whit had an argument, so in retaliation, Monty broke a window at Whit's End. He was caught by the sheriff, and Whit took him back to the house. He was sent to his room while Jana and Whit talked. He came down after, and amends were made, but as a punishment, he had to mow lawns to pay back Whit for the window.
Monty's family came to Odyssey again with his sister Jenny. He went downtown with Jenny and bumped into some of the girls from Odyssey's Children's Orchestra. While the Whittaker family was preparing for Christmas, Monty accidentally broke the angel from the nativity scene, and his mother became upset at him. Jana later talked harshly on the phone to Monty's father, and hung up before Monty could talk. In rage, Monty ran away and eventually winds up at the mall, where he finds Connie. They talk, and Monty decides to buy another glass angel for their nativity scene. While going home, Monty and Connie have a snowball fight, and Jana comes outside to join them. Monty and Jana apologize to one another, and as an amendment, Monty gives her the angel as a present.
Years later, Whit was called to the hospital to identify a victim of a plane crash who mentioned him by name. It's Monty! Monty became a Secret Service agent and was on the plane with a colleague, Derk Begs, and started arguing over a backpack of counterfeit money, which was then thrown from the plane. He escaped from the hospital and wound up at Whit's house, where he rested. He went with Whit and Detective Polehaus to Uncle Archie's Uncle Archie's Carnival, but Monty was kidnapped by Mr. Skint and Agent Tanner. He presumably stayed with them until The Stiletto stopped Agent Tanner. The Stiletto later told Whit that Monty was safe, resting in the hospital. Monty called Whit when Derk Begs woke up. (He was in a coma.) Whit told him to ask Derk about a list of numbers in the backpack they found. Monty went into Derk's room and asked him about them, but a nurse shooed him out. Later, though, Monty came back and asked him about them again, and Derk said that they were freight trains. After the freight trains were stopped at Haggler's Junkyard, Monty showed up to observe. Just then, Connie showed up with a message from Jason that said 'the plates would be found at TLC'. Monty figured out that that meant 'Trickle Lake dock C'. They went there and found Dr. Trask, whom Detective Polehaus arrested. Whit told Monty 'Well done'.
- Main article: Whittaker family.
Monty's parents, Whit's daughter Jana and Phil Dowd got divorced when he was young. His uncles are Jerry and Jason. His grandparents are John Whittaker and Jenny Whittaker. His sister is Jenny Whittaker-Dowd.
|“|| John Whittaker: Good morning, Monty.
Monty Whittaker-Dowd: Good morning, Grandpa.
|“|| Jenny Whittaker-Dowd: It's not a snow "man", Monty, it's my snow "friend".
Monty Whittaker-Dowd: Snowfriend? Good grief Jenny, where do you get this stuff? For once, couldn't you be normal and build a snowman?
Jenny Whittaker-Dowd: Precision of language, Monty. I couldn't decide if it's a male or female, so I decided to call it my snow-friend. "Say what you mean, mean what you say." That's my motto.
Monty Whittaker-Dowd: "Go stick your head in the snow." That's my motto.
Jenny Whittaker-Dowd: There you go with your adolescent trauma again.
|“|| Monty Whittaker-Dowd: Did you happen to get the number of the truck that hit me?
John Whittaker: It wasn't a truck, it was Gower's Field.
|“|| Connie Kendall: You're a man, aren't you?
Monty Whittaker-Dowd: That depends on whether my mom wants me home before dark, or wants me to mow the lawn.
|“|| Monty Whittaker-Dowd: We were told to come to Dock C at Trickle Lake. I didn't realize you had more than one dock.
John Whittaker: Well, things have changed since you and I came up here to fish.
|“|| Monty Whittaker-Dowd: Have you ever heard of counterfeit dollars in the area?
John Whittaker: We had a situation a few years ago, but that didn't lead to anything.
Monty Whittaker-Dowd: Maybe it's connected, maybe not.
|“|| Connie Kendall: Monty, you can't leave!!
Monty Whittaker-Dowd: Hey! This is one thing I can do as good as my sister! Goodbye!
|“|| Monty Whittaker-Dowd: Hi Mr. Riley, hi Eugene.
Tom Riley: Well, hello there Monty.
Eugene Meltsner: A most felicitous morning to you, Montgomery.
Monty Whittaker-Dowd: Huh? Oh, Thanks.
|“|| Connie Kendall: <reading lines to Monty> The news of it has spread...
Monty Whittaker-Dowd: The news of it has spread... Um...
Connie Kendall: Even out to these lonely...
Monty Whittaker-Dowd: The news of it has spread even out to these lonely... Um...
Connie Kendall: And nethermost...
Monty Whittaker-Dowd: And nethermost...
Connie Kendall: Regions.
Monty Whittaker-Dowd: Regions!
Connie Kendall: <exasperated> Monty!
Monty Whittaker-Dowd: Monty!