Boss of Team Rocket and the Viridian Gym Leader. So operates within the shadows, though thanks to Datamon's involvement, he had received the technology to give his underlings the power to digivolve their pokemon passed the highest level.
- Authority Equals Asskicking: He's the head of a criminal group AND the Viridian City Gym leader.
- Big Bad: He's the leader of Team Rocket, who causing some problems to the heroes, especially now that they have pseudo-digivices of their own
- Corrupt Corporate Executive: He owned Pokemon Land, an attraction park featuring giant robot Pokemon, implying that he is some sort of businessman.
- Diabolical Mastermind: The first in the Pokémon series.
- Dishing Out Dirt: As the Viridian Gym Leader, he specialize in Ground-types.
- The Don: He's a leader of a mafia-like organization
- Faux Affably Evil: He's quite polite and personable as he tells you that he's going to Take Over the World with Team Rocket, and if you oppose him he'll make you experience a world of pain.
- Infinity +1 Sword: Has been given the technology to make pseudo-digivices that digivolves organization's pokemon through the power of shadow, the super effective to all types (except for Digimon's light) from the Pokémon Colosseum series
- Man of Wealth and Taste: He's quite wealthy
- Meaningful Name: His name is pronounced GEO-vanni. The name indicates both his occupations: a Mafia Boss and a Gym Leader of Ground-type Pokémon.
- Orcus on His Throne: Operates within the shadows as The Don of a criminal organization
- Right-Hand Cat: Now a Right-Hand SABER TOOTH TIGER!
Arch-Enemy to Etemon from Digimon Adventure, brought Back from the Dead by the Dark Masters to ensure the Digidestineds never return to their world. However he had plans of his own, and For Science! he hunted down the GS Ball from Ash to unlock its secret of the sealed evolution. Even though defeated, his influence still lingers as it was he hinted at the Sealed Evolution and encouraged Team Rocket to take part in unlocking it.
- Arc Villain: He can be seen as the Big Bad of the Orange Islands arc
- A.I. Is a Crapshoot: Originally a robotic digimon, but now he only exist as an A.I. programming since his original body has been destroyed. He can however take control of other machines.
- Dragon with an Agenda: While he was revived to serve Machinedramon to battle the Digidestined, he had his own plans
- For Science!: His reasons for unlocking the sealed evolution
- Humongous Mecha: Despite being an ultimate, Datamon is Weak, but Skilled. In order to fight Ash and his pokemon, Datamon created a mech to take command.
- Unwilling Roboticisation: Captures pokemon to turn them into robots
- Weak, but Skilled: Datamon maybe an ultimate, but he's weak as a rookie. However he makes up for this with his high IQ.
Jesse, James & Meowth
Because of the Mon Wars, they have taken an interest in Digimon, wanting to present them to their boss. Of course their tactics resort to their same old trap holes and giant mechs.
- Affably Evil: Despite working for Team Rocket, they aren't as evil as other members. They can't even control the power of shadow.
- Anti-Villain: They're not as evil, they truly love their pokemon and Even Evil Has Standards.
- Back-to-Back Badasses: When reciting their mottos
- Breaking the Fourth Wall: One of the few constant wall breakers
- Catchphrase: Their intro speech ("Prepare for trouble! Make it double!...") and "Team Rocket's blasting off again!".
- Catchphrase Spouting Trio: Meowth's part maybe small, but it contributes
- Demoted To Extra: With Ash and Pikachu being closely tied in plots helping the Digidestined fighting against their enemies, Team Rocket has made little appearances troubling the boy or his friends, being just recurring enemies rather than the constant villains as they were in the anime. However with Team Rocket gaining knowledge of Digivolution, the trio may get a bigger role as time goes by.
- Crouching Moron, Hidden Badass / Let's Get Dangerous!: When they aren't being used for jokes, they are quite threatening.
- Custom Uniform: Their original white uniforms were this. All other Team Rocket grunts wear black, but they wore white symbolizing how outlandish they were from the rest of the organization.
- Damn, It Feels Good to Be a Gangster!: They all love their jobs.
- Determinators: No matter how many times they've been blasted off, they will never give up on trying to capture Pikachu.
- Drama Queens: All three of them, seriously.
- Faceship: Their iconic Meowth hot-air balloon.
- Freudian Excuse: Jessie grew up in poverty while Meowth spent much of his life as a stray. While James in contrast was part of a well-off family, his parents were cruel to him and wanted to force him to get married.
- Humongous Mecha: They sometimes utilize ridiculous mecha robots to aid their nefarious deeds, though they are always destroyed by the plot's end, sending the trio blasting off.
- In the Name of the Moon: Team Rocket's motto that they recite in every episode.
- Light Is Not Good: Unlike most of the black outfitted members, they are the only ones ever dressed in white. Even Meowth's creamy-coloured fur references this trope.
- Made of Iron: They actually credit their encounters with the protagonists and being blasted off to making them this.
- Minion with an F in Evil: To test out the new digivices, Jesse and James were used as subjects by the rest of Team Rocket, namely Butch and Cassidy
- Shoo Out the Clowns: Unlike how in "Best Wishes" they started to become serious and threatening (Prior to Decolora Adventures), the Team Rocket trio was Demoted To Extras when Ash and co. entered the Mon Wars. Although its still possible they'll be brought back into the spotlight once the Team Rocket organization gets more involved in the plot. So like Best Wishes, only with digimon being the Plot Device and not an Unova pokemon.
- Terrible Trio: The iconic team!
- True Companions: Have formed a strong bond with each other.
- A Twinkle in the Sky: "Looks like TEAM ROCKET'S BLASTING OFF AGAAAAaaaaiiiiinnn! *Ding*
- Vitriolic Best Buds: They get snappy at each other on a daily basis but are close.
Cassidy and Butch
Two recurring agents of Team Rocket, Cassidy and Butch are far more competent than Jessie, James and Meowth and wear the tradition Team Rocket black uniform rather than the trio's white outfits. They were part of unleashing the sealed evolution, by breaking Giratina out of the Distortion World. They latter appeared, having used Jesse and James to test the Team Rocket's digivice on controlling shadow.
- Accidental Misnaming: In a Running Gag, Butch is called the wrong name repeatedly - like Botch, Biff, Hutch, Bob and even Buffy.
- Always Someone Better: They were essentially versions of Jessie and James who were actually competent. Unlike Jesse and James, Butch and Cassidy were able to use the power of shadow with little problems.
- Breaking the Fourth Wall
- Butt-Monkey: Usually Butch.
- Card-Carrying Villain: if their motto is anything to go by.
- Catch-Phrase Spouting Duo: An alternate version of the usual trio's motto.
- Darker and Edgier: Than the usual trio until Best Wishes.
- Hijacking Cthulhu: Took control of the Legendary Birds!
- Large Hams
- The Rivals: To Jessie, James and Meowth.
- Terrible Trio: Alongside their on-and-off Team Pet Raticate.
- Those Two Bad Guys
- What Happened to the Mouse?: They haven't been seen for a while now.
- You Gotta Have Green Hair: Butch.