Westley, formerly known as Private Westley, was a loyal watchdog of Lord Hater's army up until the recent events that occurred in the Wander Over Yonder episode "The Little Guy". In a failed mission to capture Wander and Sylvia, Westley is left behind. His only way to get rescued is to capture Wander and Sylvia and report to Commander Peepers.
Westley wears the regulated watchdog uniform, black with red gloves and boots and a black cap with a small lightning bolt on top. Like every watchdog, he also has an eyeball for a head with a red iris. Westley is short and chubby with stubby arms and legs. He is the youngest of the watchdog army.
At the end of "The Little Guy", Westley changes his cap from one with a lightning bolt to one with a star on top, which was given to him by Wander.
Probably the most energetic of watchdogs, Westley is both a loyal soldier and strong supporter of Hater's Empire. He is shown to be a bit of a day-dreamer but determined to do his best. His short stature and weight tend to make him lag behind the other watchdogs as he lacks the same physical strength and is often clumsy. Throughout The Little Guy, during his adventures with Wander and Sylvia, Westley constantly accuses them of being the "real bad guys" and refuses to trust them (as influenced by Lord Hater). As the episode continues, Westley slowly begins to soften up to the two vagabonds until finally laying down his laser pistol. However, when Lord Hater's ship arrives, and Lord Hater himself alongside Peepers stand outside waiting for the young watchdog, Westley turns against Wander and Sylvia and turns them in. Later however, Westley plays a trick in helping the vagabonds to escape Hater's ship and appearing to die in a fake attempt to stop them.
At the very end of the episode, Westley is given his new hat, throws away his laser gun, and parts as good friends with Wander and Sylvia.
Westley and Wander's relationship evolved over the majority of the episode, as Wander kept trying to make Westley good but denied it since Lord Hater said that Wander and Sylvia were the bad guys. However, at the end, Westley befriended Wander and Sylvia.
Their exact relationship is unknown, but that Sylvia at first, did not like Westley, as Westley was a first Watchdog and a "trained killer", however, Sylvia sniffled during the end, and now, they are friends.
Westley wanted to meet Lord Hater and get he medal of evil, Lord Hater was proud of Westley as he was the first and only Watchdog to capture Wander and Sylvia, when Westley "died", Hater was the most upset person over Westley's "death", however, in the animatic, he's still crying, and claims it's because Wander and Sylvia got away again, and asked who Westley was.
Their exact relationship is unknown, but it is implied that Peepers did not think of Westley too highly. While on the communicator with him, Peepers laughed uncontrollably when Westley claimed to have captured Wander and Sylvia. When Hater arrived at the rendezvous point, Peepers said, "I knew he wasn't Watchdog material!" However, Peepers was one of the people most upset over Westley's "death".
It is unknown how Westley felt about the other Watchdogs but the watchdogs didn't seem to like Westley as they thought he was annoying, and always teased him. However, when he "captured" Wander and Sylvia on his own, they treated him with more respect, and they were sad over his "death".
- Westley, along side Peepers, Moose, Bob, Pete, and Teddy, is one of the only named Watchdogs thus far.
- Westley is the first antagonist to turn good.
- Westley was named after Westley Joseph, the brother of Ben Joseph, who wrote Westley's episode.