May and her friends met Drew while she practiced with her Beautifly on a beach near Slateport City in Now That's Flower Power!. Despite his cutting remarks and attitude, which tend to anger May, he is not a villain and teases May simply to push her into becoming a better coordinator. Drew's skill has been a continuous inspiration for May on her quest to be a Top Coordinator.
In his first battle against May, he pitted his Roselia up against her Beautifly. May managed to gain the edge, much to Drew's shock, but the match was cut short by Team Rocket.
Drew returned in Pros and Con Artists, competing in the Fallarbor Town Contest, where May discovered he now has three contest ribbons. Before the contest began, Drew had his Roselia battle Ash, pitting him against Taillow. Drew and Roselia emerged victorious. During the contest, he battled against Grace, but lost to her Medicham. At the end of the competition, Drew congratulates May on her victory by giving her a rose. The gesture of handing a rose to May is repeated in other episodes and is seen by some fans as a hint toward a romantic relationship between them.
While watching a different Roselia, May is reminded of their rivalry.
In A Fan with a Plan, Drew was assaulted by a fan club in the Pokémon Center in Rubello Town. Before the contest, May sees Drew practicing outside with his new Pokémon, Masquerain. Drew wins his fourth ribbon using his Roselia in the appeals round, and his Masquerain in the battle round.
Notably, Drew is runner-up in the Hoenn Grand Festival, having defeated May in the quarterfinals with his Flygon and Roselia, but losing to Robert in the finals.
In Going for Choke!, he helps Ash, Brock, and Max out of traps and tricks prepared by Team Rocket and Harley.
Drew also revealed in May, We Harley Drew'd Ya that he had been training an Absol for the KantoGrand Festival. During the quarterfinals of the festival, he lost to May, who was ultimately defeated by Solidad.
In The Unbeatable Lightness of Seeing, he reveals that he will travel to Johto to participate in contests there.
Like Ash's main rival in the original series, Gary, Drew is portrayed as being confident, critical, and popular among his supporters, though he isn't as overly insulting as Gary was. Though [[May (anime)| and Drew remain rivals throughout the series, Drew becomes less insulting towards May and more kind and friendly as time goes on. His signature greeting is flicking his hair in a charming manner and can usually be seen with a rose in his hand.
In the Kanto Contests, Drew is often seen even at contests in which he is not competing. It is hinted that he comes to support May.
He was runner-up to Robert in the HoennGrand Festival and was among the top eight in the KantoGrand Festival, losing to May. Although he has yet to achieve his goal of Top Coordinator, he is regarded as one of the best coordinators.
No one knows when he caught it. It first appeared in the Rubel Town double contest. It is very beautiful and often used in the first round. It used Bubble, Ice Beam, Silver Wind, and Hidden Power, among others.