And St Kilda have fended off interest from Melbourne, Essendon and North Melbourne to re-sign Marcus Windhager on a fresh four-year deal until the end of 2029.
Just days after the Demons unveiled Steven King as their new senior coach, multiple reports have surfaced about Melbourne's desire to move on from May as they turn their focus to youth.
The 33-year-old is contracted with Melbourne until the end of 2026, but with the Demons keen to bring younger players up through the ranks, it seems there is no longer room for the 251-game veteran.
The premiership defender joined Melbourne from Gold Coast at the end of 2018 and played a key role in the Demons' 2021 flag.
But his time at the Demons has also been littered with controversy.
May copped a club-imposed one-match ban after engaging in an alcohol-fuelled fight with teammate Jake Melksham during a night out in 2022.
Melksham ended up needing surgery after the hand he injured in the fight became infected.
"Sometimes guys can get a little bit competitive with the banter and go a little bit overboard. We certainly made an error of judgement in that time," May said during his apology in the wake of that fight.
May's on-field frustrations at his teammates also bubbled over at times, most noticeably in this year's one-point King's Birthday loss to Collingwood when he confronted Max Gawn after the skipper made a horror late blooper.
Gawn pushed an angry May away in frustration, with the incident becoming a huge talking point.
Vision of May appearing to ignore Gawn's address to the player group following the club's final match this year raised further eyebrows.
With Melbourne set for at least a mini rebuilding period, new coach King faces a big task to convince midfield stars Christian Petracca and Clayton Oliver to stay.
Meanwhile, veteran Adelaide defender Brodie Smith has announced his retirement after 273 games across 15 seasons with the Crows.
The 33-year-old played just 11 games this season, but he did feature in the club's straight-sets finals exit.
Adelaide forward Taylor Walker is still yet to confirm whether he will retire or play on for one more year.
Windhager's new deal follows an impressive off-season from the Saints, who have also re-signed Nasiah Wanganeen-Milera and are set to welcome in free agents Tom De Koning and Jack Silvagni.
West Coast premiership forward Liam Ryan and GWS defender Leek Aleer have also requested moves to the Saints.
In other news, star Brisbane attacker Zac Bailey has done his best to sidestep questions about his future.
Bailey is contracted with the Lions for next year, but there are already a number of clubs - including Adelaide and Essendon - circling him following his maiden All-Australian campaign.
The soon-to-be 26-year-old says he's only focusing on Saturday's preliminary final against Collingwood at the MCG rather than the trade rumours surrounding him.
"I absolutely love it here. For me, I haven't really given it (my future) too much thought," Bailey said.
"For me, the next two weeks are pretty important for this club as a whole, and we've got a really big opportunity.
"That's where all my focus has been. I've got another year-and-a-half here at the club, so I think there's plenty of time to sort that stuff out."
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