May will return from a controversial three-game ban for his milestone match against Hawthorn on Saturday afternoon.
The 33-year-old, who is contracted until the end of next season, is already showing signs of a potential coaching career, Melbourne's interim boss Troy Chaplin says.
"It's exciting for Maysie, his 250 games," Chaplin said on Thursday.
"Started out at the Gold Coast Suns and them came across here and is a premiership player as well.
"I have really enjoyed coaching Maysie, been really close with him obviously with coaching the defenders and team defence for a long period of time."
Chaplin said while dual All Australian May's competitive streak was renowned, he was also tactically astute.
"He is a competitive guy, he loves to win," he said.
"But what I have really seen in the last few years is his care for his teammates.
"He could make a great coach some day, if that's something that he wanted to do post-footy.
"The time that he spends with the young guys ... and coaching them through defensive positioning, different plays, sitting down watching their tape and really taking a keen interest in their development, has been fantastic the last few years."
May, in his seventh season with Melbourne after eight on the Gold Coast, returns against the Hawks after being suspended for a collision with Carlton's Francis Evans.
The MCG fixture will be Chaplin's second in charge after Simon Goodwin's sacking as head coach.
The Western Bulldogs edged the Demons by six points last week, though Chaplin was proud of his players.
"Obviously you're in charge of the program now and a lot more meetings and a lot more touchpoints with different people, but I really enjoyed it," he said.
"It was a great effort by the boys, we were right in it until the end of the game and to see them fight it out, it showed a lot of maturity."
Meanwhile, the Demons have announced a seven-person panel charged with finding Goodwin's permanent replacement.
Former Essendon captain Jobe Watson, Melbourne Storm director Frank Ponissi and human resources executive Meahan Callaghan are the members on the panel not linked with the Demons.
Club president Brad Green, director Steve Smith, incoming CEO Paul Guerra and football manager Alan Richardson round out the panel aiming to name the next coach in mid-September.
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