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Drew made his debut appearance in Now that’s Flower Power!. Like Ash’s main rival, Gary, Drew is portrayed as being confident, critical, and popular among his supporters, though generally not as overly insulting as Gary initially was.

When Drew had participated in his very first contest, he had lost badly to a strong coordinator named Solidad. He said the loss was so heart-breaking for him it had even made him cry. Though he had suffered a defeat in his first contest, he endeavored to become a better coordinator and has succeeded to a good extent. He used to be very prone to nervousness when he started his career as a coordinator.

He used to taunt May when he first met her because she used to be like him when he first started out. Even though his comments and attitude may have angered May, he still provides a helping hand whenever she needs it. Drew’s skills have been a continuing inspiration for May to better herself as a coordinator.

When Drew participated at the Slateport City Contest in Win, Lose or Drew!, he and his Roselia defeated May and her Beautifly, but went on to lose to Robert and his Milotic. Drew shows up again in Pros and Con Artists for the Fallarbor Town Contest. During the contest, however, he loses to Grace and her Medicham. Following the contest, Drew congratulates the winner, May, by giving her a rose. The gesture (which is repeated in later encounters) is seen by some fans to be a hint towards a romantic relationship between the two but no direct hints have been shown.

Notably, Drew made it to the finals of the Hoenn Grand Festival in Rhapsody in Drew by beating May in the semi-finals. However, he lost in the finals to Robert, who also beat him in the Slateport City contest, and was placed second.

Afterwards he decided to go for the Contests in the Kanto region along with May and their other rival, Harley. In May, We Harley Drew’d Ya!, he was reunited with his old rival and friend Solidad, who had defeated him a long time ago. During the Kanto Grand Festival, he lost to May in the semi-finals who was placed in the Top 4.

In The Unbeatable Lightness of Seeing, he said he would be traveling to Johto to participate in the contests in that region. He has the Contest Passes to compete in Hoenn, Kanto and Johto as well and as of Pruning a Passel of Pals! he had made cameo appearances in a A Full Course Tag Battle! flashback, watching May perform at the Wallace Cup.