Tricky made his first appearance in the 1997 N64 game Diddy Kong Racing where he served as the first boss of the game and presided over Dino Domain. Later, in 2002's Star Fox Adventures Dinosaur Planet, he appeared as a young lad where he was prince of the Earthwalker Tribe. He eventually made a third appearance in Star Fox Assault before making his way to Timber's Island sometime in the early to mid 1990s. It's unclear how much time Tricky spent ruling Sauria before traveling to Earth and how much time Tricky spent ruling over Dino Domain before Diddy Kong Racing. However the evidence makes it pretty clear that whenever Star Fox takes place it's in the recent past.
Star Fox Adventures
Prince Tricky is a dinosaur in the Earth Walker tribe in Star Fox Adventures. He is the son King and Queen Earth Walker, making him Prince of the Earth Walker Tribe. His largest role is during the events of Star Fox Adventures, where he serves as a companion of Fox McCloud during the majority of the game. Fox saves Tricky from the Sharp Claw tribe (ruled by General Scales), and Tricky decided to help out Fox for the rest of the adventure.
Tricky has a variety of abilities, all fueled by Grub Tubs (a type of mushroom). These abilities are, at many times, required to continue in the game. Some of his abilities include digging holes, breathing fire, opening up small holes, and fetching a ball. After Fox and Tricky saved Sauria (Tricky's home planet), Tricky was given an honorary position in the Star Fox team.
Life on Sauria post Adventures
Tricky matured and grew up to become King. He appeared in Star Fox Assault when Sauria was being attacked by the Aparoids. Fox and the rest of the Star Fox team came to defeat the Aparoids, and after doing so, visited with Tricky. Tricky was excited to see his good friend Fox, as well as Krystal. Fox convinced Tricky to fix Sauria, and Tricky commented that Fox and Krystal could come back for their honeymoon, embarrassing Fox (due to his feelings towards Krystal). Tricky also appeared as a trophy in Super Smash Bros. Brawl.
Diddy Kong Racing
Tricky is later introduced as the boastful boss of the first world, Dino Domain. By this point in the cannon Tricky has moved country from Lylat to Earth and has made himself at home. His looks have hardened, his voice roughened and he's taken the time to have statues of himself carved into the summit of his spiral-shaped mountain he's wont to race up. Like all the bosses of Diddy Kong Racing Tricky had been brainwashed by Wizpig at the start of the game.
Once Diddy and friends beat all the races of Dino Domain they challenged Tricky to a race. Tricky took off a second early but still was felled by the hero. He congratulated them, gave them and gave them a new challenge. The Silver Coin challenge. Diddy and friends had to revisit all the tracks of Dino Domain, collect all 8 silver coins and WIN before they could challenge Tricky again. They did so and, despite Tricky being twice as fast this time, won out. This broke the curse on Tricky. He thanked the heroes by offering them the piece of Wizpig's amulet he'd been entrusted.
In the end Tricky (and two other Triceratops- possibly his children) joined Diddy Kong's posse and 2 of the other liberated bosses to celebrate the downfall of Wizpig.
The connection between young Tricky and old Tricky is sometimes debated. It is not explicitly said in game that they're the same character however there's a lot of evidence which shows that they are. First and foremost, Rare said they were saying "in a sense, they are the same."
Another way of looking at it is looking at the lineage. Star Fox Adventures started out as a sequel to Diddy Kong Racing. It soon became Dinosaur Planet and then morphed once more into Star Fox Adventures: Dinosaur Planet. It is this lineage by which we owe Tricky.
The young Prince Tricky is voiced by Hirohiko Kakegawa.