DEAN Cox describes trading out Will Hayward and Ollie Florent in last year's blockbuster move to land Charlie Curnow as the "toughest decision" of his coaching career as the Swans targeted the Carlton star to supercharge their flag push.

Hayward and Florent were both traded to Carlton in separate deadline day deals that saw Curnow head to the Swans despite having four years remaining on his contract, with the Swans pushing their popular duo to seek trades while also having their own long-term deals at Sydney.

Cox, who took over the senior role for 2025 after being a long-term assistant at the Swans, told AFL.com.au that trading the pair of 184-gamers had been the most challenging call of his time in coaching.

"It was the toughest decision I've had in my coaching career by far to date," he said.

"I've been at the football club now for nine years, I've spent a lot of time with Will and Ollie, and the hardest part as well is that we finished six weeks before trade period starts with so much uncertainty around whether players want to come to your club, whether you can get them to your club, how serious stuff is. The dialogue through all of that is really difficult with the player. 

"The hard part is dealing with the player versus the person. That's the part I found tough to do. But my role is to make decisions for the football club and to try and make this football program as good as it can be. Unfortunately, Carlton don't want your 43rd and 44th best player with the calibre of player that Charlie is so it had to fall that way.

"That's the hard part of having the conversations during it as well, because there's so many scenarios that come at you like, 'Is it done? Can it be done? How do we do it?'

"One thing I wanted to make sure is before Charlie said he wanted to come here there was a position of [us] saying 'We can't give up names' because I didn't want to do that. Part of it is if I'm speaking to a player, I don't want their name to get put through without actually hearing it from me. That's why it moved quick late."

Sydney has been a destination club for power forwards, but with Lance Franklin's move at the end of 2013 coming as a free agent, having to trade out regular, experienced players to land a target was new ground for the club.  

The final deal was lodged in the minutes before the end of the trade window, but had been in Curnow's mind for months, with AFL.com.au reporting in July that Curnow was open to moving to one of three clubs: Sydney, Geelong or Gold Coast. The Suns bowed out when they prioritised Christian Petracca, while Geelong offered three first-round picks for Curnow but couldn't land a deal. 

Cox met with Curnow for the first time at the end of Carlton's season, and then was part of his tour of the club's world-class facilities during the frantic trade period.

"The catch-up wasn't a really hard sell, it wasn't really 'This is what we can do'. It wasn't a really hard sell. It was more me getting to know Charlie and him getting to know me. We hadn't met before. It was just a catch up, there wasn't a computer out, it was just getting to know each other," Cox said.

"And if the possibility was to eventuate, then what it could look like. Then the meeting we had late was purely because he wanted to respect Carlton and go to their best and fairest. As soon as that was done, we were a chance to have a chat with him and we only had three days of the trade period left so it had to be done then. 

"We wanted to show Charlie what the footy club was about – him and [partner] Tiana. That was really important that when they are making a move as a couple, it's not just about the footballer but what everything else looks like outside of that."

Cox was walking the streets of Bondi on the last night of the trade period, with former Swans assistant Jarrad McVeigh hosting a farewell event before heading to live in Chicago. The former West Coast champion spent more than two hours walking with his phone jammed to his ear taking calls and getting updates, with the deal nearly falling over in the final 30 minutes.

"I got a phone call from [Swans football boss] Leon (Cameron) that, 'This is not going to happen, it doesn't look like this is going to happen'. I chatted to him for a little bit but then when it did, it was good to finally get done. [McVeigh's event] was almost done by the time I walked in."

The addition of Curnow adds star power to the Swans, who fell short in the 2022 and 2024 Grand Finals and missed the top eight last year. And it also adds more expectation on the 28-year-old and his new club as he spearheads their flag push, which will start in Opening Round against Carlton in a first-up grudge match. 

"His work ethic, his training standards, ever since he got here have been at the highest level," Cox said.

"Our expectations of Charlie aren't a certain number of goals or how he impacts the scoreboard. Ours is about the opportunity he [brings] playing in our forward line. That's about teaching others around him, it's about testing our defenders to make them better players as well. He obviously knows where the goals are and he can run and cover the ground so well that he's not just required to play out of the square."

Subscribe to the Your Coach podcast to listen to Cal Twomey's full interview with Sydney coach Dean Cox this week.