Clayton Oliver’s uncertain future is once again overshadowing Melbourne’s best and fairest night for a second consecutive season, with Geelong reportedly showing interest in the unsettled midfielder.

With the AFL’s trade period fast approaching, clubs have officially started lodging offers to free agents as of Friday morning, signaling the start of the “silly season.” The trade period itself begins on Monday.

Oliver, despite being under contract with Melbourne until the end of 2030, met with Geelong this week as he explores his options. Melbourne has reportedly been open to shopping Oliver around, leading the four-time best and fairest winner to test his market value and consider potential moves.

The meeting between Clayton Oliver and Geelong reportedly took place at ruckman Rhys Stanley’s farm, with defender Tom Stewart and Geelong officials present. At Geelong’s best and fairest night on Thursday, Stewart confirmed that the meeting with the 27-year-old midfielder had taken place.

“It was good. Obviously, any sort of talent we can attract to the club is important for us,” Stewart told the Seven Network. “I had the opportunity to meet with him, and it’s an interesting thing for me at this stage of my career, but it went well—he’s a good man.”

Stewart emphasized that the meeting wasn’t about pitching anything in particular but more about giving Oliver insight into Geelong’s culture. “It’s just sort of enlightening him as to what we’re about at the footy club, the things that we hold dear, and the things that we really value,” he explained.

While a potential deal is far from certain, and many things need to fall into place, Stewart added that if they can attract talent like Oliver, it would align with the club’s goals. Any trade would likely require Melbourne to cover part of Oliver’s substantial salary.

Geelong will have to be smart in the market as they are also eyeing Western Bulldog Bailey Smith.  (Joel Carrett/AAP PHOTOS)
Geelong will have to be smart in the market as they are also eyeing Western Bulldog Bailey Smith. (Joel Carrett/AAP PHOTOS)

Geelong would need to get creative in terms of trade capital, given their first-round draft pick will likely be used to obtain Western Bulldogs midfielder Bailey Smith.

Melbourne’s best and fairest is on Friday night.

Last year, president Gary Pert released a statement via a letter to members just hours before the event, saying Oliver would not be traded.

That could happen again.

The supremely gifted midfielder has struggled with his fitness and off-field issues over the past two years.

Coach Simon Goodwin has made it clear he wants to keep both Oliver and Christian Petracca, who committed to the Demons for 2025 after agitating for a trade.

The unrest once again flies in the face of comments from Pert late last year Melbourne’s culture was the best he had seen in 40 years.

Several free agency moves could be signed off as early as Friday, with some clubs nervously awaiting compensation.

St Kilda defender Josh Battle is set to join Hawthorn, while GWS pair Isaac Cumming and Harry Perryman are bound for Adelaide and Collingwood respectively.