Admitting it has been "uncomfortable" and "not ideal", Essendon have refused captain Zach Merrett's bid to join Hawthorn.
Hold tight - we’re checking permissions before loading more content
While Sydney secured a deal for Carlton star Charlie Curnow only a few minutes before Wednesday night's AFL trade deadline, the Bombers held firm in fraught negotiations.
Merrett's manager Tom Petroro, who had said earlier on Wednesday the star midfielder was "all in" on joining the Hawks, was seen on video footage having animated discussions with Hawthorn officials as it became clear there would be no deal.
The Essendon star was the biggest name among several players who were unable to secure trades.
St Kilda's Rowan Marshall (Geelong), two-time Brisbane premiership player Call Ah Chee (Adelaide) and Western Bulldogs defender Buku Khamis (Carlton) also failed to move.
Ah Chee's manager Ben Williams was seething after no deal was struck with the Lions, fronting the media and saying his player would join the Crows through the pre-season draft.
North Melbourne admit Jy Simpkin is unlikely to remain captain after they refused to trade him to Collingwood.
Essendon list boss Matt Rosa would not buy into whether Merrett will stay captain, only saying the Bombers will decide their player leadership in the off-season.
Star Melbourne midfielders Christian Petracca (Gold Coast) and Clayton Oliver (GWS) also are heading north, while St Kilda captain Jack Steele is off to Melbourne.
Jamarra Ugle-Hagan, the 2020 No.1 draft pick, was traded by the Western Bulldogs to Gold Coast after not playing at all this year because of personal issues.
Soon after the 7.30pm deadline, Rosa told media Essendon had negotiations with Hawthorn "out of respect" for Merrett.
The Hawks' initial offer only arrived on Tuesday and was rejected out of hand.
They used a trade of draft picks with Carlton on Wednesday to strength the offer, but again Essendon did not budge.
Merrett blindsided the Bombers a month ago when news broke he had met with Hawthorn coach Sam Mitchell.
He is signed until the end of 2027, but was desperate to leave for Hawthorn as he chases team success.
"Not ideal ... it's been uncomfortable. We didn't want to be in this situation," Rosa said.
"We've been really clear all along that Zach's a required player, he's an important part of what we're doing. We believe in what we're doing.
"We've kept our players in the loop the whole time, our staff. Zach is really well-liked, the players want him back.
"Zach understands that. He's a professional and we look forward to him coming back over summer."
Rosa conceded the start of pre-season training might be "awkward", but was adamant Merrett's bid to leave would not destabilise the club as it tries to rise out of the bottom four.
"No - we're confident we'll all work together. We'll continue to have open dialogue," he said.
Hawthorn list boss Mark McKenzie did not rule out another bid for Merrett in 12 months' time, adding they were "definitely disappointed" the trade did not happen.
"We put our best foot forward with the deal we thought was very strong and reasonable. It just didn't get done," McKenzie said.
"What we have done is put ourselves in a great position for this year's draft, but then to go again next year.
"We want to be aggressive, we haven't made a secret out of ... going after those high-end talented players and that will happen again."
Ollie Florent, part of the original bid, was also traded to Carlton in a separate deal.
Carlton football boss Chris Davies said having Hayward in the deal made it "effectively" four first-round selections.
"We were obviously looking for the best-possible deal if we were going to do it. With half an hour to go, I didn't think it was going to get done," Davies said.
"Then Sydney came to the party with something we'd been asking for over the last 24 hours. We're really pleased."
Curnow, Carlton's two-time Coleman Medallist, was the biggest name to find a new home.
Sydney gave up their next three round-one draft picks and player Will Hayward to Carlton for Curnow. They upped the offer after the Blues earlier on Wednesday rejected their first proposal.
Dual Coleman Medal winner Curnow wanted to head to Geelong or Sydney, with a move north looking more likely after he toured the Swans' facilities on Monday.
Carlton had indicated only a "Godfather deal" would shift their position on Curnow, contracted until the end of 2029.
Geelong's offer last week of first-round selections in the next three drafts for Curnow was swiftly rejected.
Hawthorn also traded Changkuoth Jiath to Melbourne for pick 42 and sent Jai Serong to Sydney in a deal that featured future draft selections.