Benny showed up in "Tricks of the Trade" as a Trainer trying to make a trade at Palmpona's annual Pokémon Swap Meet. He had a Wobbuffet he was hoping to swap for something new, though finding the right deal proved trickier than expected. Ash and the group pitched in to help him find a willing trader. He thought about approaching Ash about his Tauros for a second, but bailed on the idea after hearing Ash say he wasn't interested in trading. A trainer with a Stantler seemed interested until he got cold feet and decided he'd rather hunt for a Flying-type instead.
Everything got chaotic when the Magikarp salesman knocked into Jessie while running from James. She crashed into a nearby trade machine that already had Benny's Wobbuffet loaded in it—and her Lickitung's Poké Ball fell in right after. The machine processed the swap before anyone realized what was happening. Jessie grabbed what she thought was her Lickitung and took off, clueless that she'd actually walked away with Wobbuffet.
By episode's end, Benny was happily showing off his new Lickitung to Ash and the others. He shouted after Jessie in the distance, promising to look after Lickitung and asking her to do the same for Wobbuffet.
Content compiled by AnimeList.moe from publicly available sources.