Since the Pokemon anime’s 1997 debut, Team Rocket has launched countless antics and schemes to try and steal Trainers' Pokemon. Team Rocket has had its fair share of redeemable moments over the years, and has often been swiftly rebuffed. Nevertheless, the dastardly trio of Jesse, James, and Meowth remained relentless, laughable, and exceedingly optimistic.

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Premiering in Pokemon Episode 2: Pokemon Emergency, Team Rocket was introduced to 10-year-old Trainer Ash Ketchum. In a turn of events, the trio underestimated the power of the young battler and his Electric Mouse Pokemon, to their detriment. Once the Team Rocket trio realized the power of Ash’s Pikachu, it became their number one target. Team Rocket has proven it will do whatever it takes to procure Pikachu, and sometimes they successfully outwit or defeat Ash with their schemes.

7 The Team Rocket Trio Plunders Pokemon League Contestants

Pokemon: Jessie and James from Team Rocket Are In Disguise Collecting Poke Balls From Trainers

In Episode 78: “A Friend Indeed,” Team Rocket follows Ash and friends to the Pokemon League Competition. Ash is blissfully unaware of the presence of his foes. Under the guise of "Poke Ball Inspectors" (They're Masters of Disguise after all), Team Rocket successfully lures hundreds of Poke Balls into their clutches, including Ash’s Pikachu.

Ash doesn’t suspect Team Rocket until after he hands over his entire team of Pokemon. The Team Rocket Trio then makes a quick getaway in a van. This is one of the most successful plans executed by the trio. With Ash and some of his formidable friends pursuing them on foot, Team Rocket had the upper hand until resting nearby.

6 Team Rocket Recruits The Squirtle Squad To Do Their Bidding

Pokemon: Team Rocket's Meowth Claws Ash's Face

In Episode 12: “Here Comes the Squirtle Squad,” Ash meets the mischievous (and adorable) Squirtle Squad. It isn’t long before the Squirtle Squad finds Team Rocket and quickly detains them. While Team Rocket is out of commission, and their lunch is commandeered, the quick-witted Meowth convinces the Squirtle Squad to do their bidding.

Ash is fishing nearby when Pikachu is severely injured. Meowth and the Squirtle Squad capture Pikachu. Ash, helpless in the situation, is quickly subdued by Team Rocket's newest Poke-Grunts. Pikachu is in critical condition, and Ash is left to beg Meowth and The Squirtle Squad for mercy to help his injured Pikachu.

5 Team Rocket Tricks Ash And Friends Onto An Ill-Fated Ship

Pokemon: Jessie and James From Team Rocket Giving Ash, Brock and Misty Free Tickets To St. Anne Cruise

In Episode 15, “Battle Aboard the St. Anne,” Team Rocket leader Giovanni assigns Team Rocket to give away tickets for the St. Anne cruise to Pokemon Trainers. He informs his lackeys that his team is preparing for a major heist onboard. Team Rocket, in another of their cunning disguises, gives away the cruise tickets.

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Ash is suspicious, but eventually accepts. After setting sail, the enigmatic Team Rocket initiates the plan to confiscate the many Pokemon on board, but they didn't count on the ship sinking in the process. Although Team Rocket got the better of Ash and his friends by tricking them into boarding, they all ultimately received the same consequence for being aboard the ill-fated ship.

4 Team Rocket Grunts Get Ash Arrested

Pokemon: Misty Escaped While Ash, Brock and Todd Are Held Inside Team Rocket's Jail Cell

In Episode 52, “The Breeding Center Secret,” the newest Team Rocket duo, Butch and Cassidy, make their first appearance. They appear to have a more careful approach to procuring Trainer's Pokemon in mind, and it doesn’t take long to show just how favored they are by mysterious Rocket leader Giovanni. Butch and Cassidy establish a Pokemon Breeding Center to “fix” Trainers’ Pokemon woes.

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Ash and his friends get caught while investigating the suspicious Breeding Center. Butch and Cassidy report the intruders for Pokemon theft, landing Ash, his friends, and the rival Rocket Trio in the slammer. Fortunately, Misty (who embarks on quite a journey over the course of the anime) and Pikachu were able to find evidence to free their friends.

3 Team Rocket Duo Turns Pikachu Against Ash

Pokemon: Hypnosis Turns Pikachu Evil With Red Glowing Eyes And Powerful Electric Attack

In Episode 86, “Pikachu Revolts,” Team Rocket duo Butch and Cassidy, hatch another clever plot to acquire large numbers of Pokemon. Ash arrives at Mandarin Island and, right away, the Pokemon turn against their Trainers and disappear. Butch and Cassidy acquire a Drowzee.

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While attached to Team Rocket equipment, Drowzee’s Hypnosis attack turns Pokemon in the area against their Trainers. Ash finds the Rocket Lab, where Team Rocket's frightful Psychic-type Drowzee sends the hypnotized Pokemon to attack him (including his own Pikachu). Team Rocket had the advantage until Ash takes the brunt of the attack on top of the Team Rocket Hypnosis equipment, freeing the Pokemon.

2 Team Rocket Finally Defeats Ash

Pokemon: Ash, Rowlett And Pikachu Are Defeated In Battle By Jessie And James From Team Rocket

In Episode 12 (Sun and Moon), “The Sun, The Scare, The Secret Lair,” Ash stumbles across the Team Rocket Trio along the beach and begins to battle Jesse and James. Using his Rowlett (popular starter Pokemon that it is) and Pikachu, he faces his foes' Mareanie and powerful Mimikyu.

They are evenly matched until Mimikyu’s hatred for Pikachu causes it to release a major attack, which leaves Pikachu unable to battle. Mimikyu is prepared to deliver a final blow to the beloved Pokemon when Team Rocket and their critters are scooped up by a Bewear and carried away. This is the first time in the series that Team Rocket defeated Ash and Pikachu.

1 The Iron Masked Marauder Stomps On Ash

Pokemon: Team Rocket's Iron Masked Marauder Fights Ash While Being Attacked By A Flock Of Wild Pidgeys

In the movie “Pokemon 4ever,” Ash encounters a deadly foe fans consider one of the most sinister villains in the series: The Iron Masked Marauder. He is an elite member of Team Rocket who seeks out the Mythical Pokemon Celebi, in hopes to overthrow Giovanni as leader of the dastardly team.

The Iron Masked Marauder uses special Poke Balls that turn a Pokemon evil. He finds Celebi with Ash and quickly catches the Mythical Pokemon in a Dark Ball. Ash, powerless to fight off the towering villain, grasps Celebi’s Poke Ball with all his might. The Iron Masked Marauder stomps on Ash’s hands, crushing them until Ash loses the struggle, as well as Celebi. Ash was completely outmatched as he experienced the brutality of Team Rocket.

Pokemon is available to stream on Netflix, Prime Video, and on Pokemon.tv.

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