Max and Monty (full names Maximilian and Montgomery) are twin dump trucks that work for Miss Jenny Packard.
Max and Monty are devious trucks who often cause trouble, but are often scolded severely by Miss Jenny. Despite being unruly at times with dangerous stunts, they both have a good side – somewhere – and do their work like everyone else. However, they are still extremely rude and unruly.
Max and Monty were sent by Miss Jenny to help out at the Quarry. They were upset with Isobella due to Miss Jenny praising her, and harassed her on the way to the worksite. However, they were caught up in an accident where Max dumped his load of rocks into Monty's path. They couldn't be repaired due to Isobella's trailer full of repair parts being destroyed.
The pair was on their way to the quarry when they found Butch broken down. Rather than help however, they instead joke about his dilemma and continue on their way to the Quarry.
When Bertram presented his spoken-word poetry, the dump trucks came into the Quarry. They were extremely annoyed by Bertram's poetry, and Monty pointed out that the poem sounded incredibly familiar.
Max and Monty are a pair of rough and tumble thugs on the construction site. They love to travel at dangerous speeds and often cause accidents due to their desire to disobey orders. They can be very rude to the other machines and engines on Sodor, and rarely think about anyone besides themselves. Very competitive and arrogant, the the twins tend to argue quite frequently!
- Season 1: The Old Warrior (cameo), Double Whammy (Max only, cameo)
- Season 2: Breakdown Blues, Two Hearts Burn Together (Max only, cameo), Pigeon Hunting (cameo), Serendipity, Scot-free (Max or Monty cameo), Mavis and the Tornado (cameo), Rosie (cameo), Young Tucker (cameo), Rock-Star, Munitions (cameo), Blunderbuss (cameo), Swan Dive (Max or Monty cameo), Luke and Millie's Blue Mountain Adventure (cameo), Aura of Menace, All the World's a Stage (cameo), Swashbuckler
- Season 3: Marion Saves the Day (cameo), Samson, BoCo, and the Man in the Hills