L-R: Miles Bergman, Harrison Jones, Harry Himmelberg. Pictures: AFL Photos

Every Thursday AFL.com.au presents Inside Trading, with breaking news and the best analysis of the AFL trade landscape covering contracts, re-signings, free agents, the AFL Draft and industry insights.

GIANTS TO PUT LONG-TERM DEAL TO FREE AGENT

GREATER Western Sydney is prepared to offer its star free agent Harry Himmelberg a five-year deal to retain his signature, with talks over his future expected to ramp up in the coming weeks.

Himmelberg has parked contract discussions throughout the start of the season but remains one of the competition's most sought after key-position targets and is expected to attract lucrative offers elsewhere as a restricted free agent.

However, the Giants remain confident of keeping Himmelberg, with the club's head of football Jason McCartney telling AFL.com.au's trade and draft show Gettable this week that it would put forward an offer as long as five years for the versatile 27-year-old.

"Yeah, absolutely," McCartney said.

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"The one with Harry is a little bit different because he was drafted as a 19-year-old. He is that year older than the traditional eight-year free agent at 26. But, touch wood, he's been a player that's been really consistent and very versatile and he's also been durable.

"We'd definitely look for a long-term contract with Harry around that and he's known that from the very early stages in our conversations and what his manager would be talking to him about."

The Giants will look to settle Himmelberg in a key defensive post across the second half of the season, having started forward under new coach Adam Kingsley, with McCartney expecting contract talks to heat up around the club's round 15 bye.

"It's been consistent right through," McCartney said.

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"I completely understand why Harry was going to take some time. People might think, 'gee that's a bit strange … he's been there eight years'. But for Harry, it's all new too. He's getting a feel and wanted to get a good look at what this coaching structure would look like and our style of play and program.

"We knew right from the very early stages, it was probably going to be something that would ramp up maybe at the midway point of the year around the bye. We're anticipating there will be further discussions over the next couple of weeks." – Riley Beveridge

STARRING SAINT TO HIT TRIGGER

ST KILDA has a backlog of list management decisions to make in the second half of 2023, but Mason Wood won't be one of them. 

The 29-year-old is about to hit a trigger that will secure him another year at Moorabbin.

Wood signed a one-year extension last October with a games clause that will see him remain at RSEA Park for a fourth season.

TRADE HUB All the latest player movement news

Wood has been a revelation this season and will be considered on a wing in the All-Australian side if he maintains this form across the back end of the season. 

After being delisted by North Melbourne at the end of 2020, Wood has played 39 games for the Saints to emerge as one of the finds of the pre-season supplemental selection period since it was introduced in 2018. 

Mason Wood with fans after the R3 match between St Kilda and Essendon at the MCG on April 1, 2023. Picture: Getty Images/AFL Photos

Saints list boss Stephen Silvagni, head of talent and acquisition Graeme Allan and senior coach Ross Lyon have spent the first half of the year assessing the state of the list and will make some decisions in the coming months. 

Free agent Jade Gresham is the biggest name on that list, while Zak Jones and Jack Higgins are out of contract, as well as former first-round picks Hunter Clark and Nick Coffield. Inside Trading reported last month Higgins is in talks for a multi-year extension after his strong first half of the season. 

Liam Stocker has played every game since being signed during the SSP window in January and will be rewarded with an extension, while Ryan Byrnes is in discussions for a new deal after playing the first 11 games under Lyon. – Josh Gabelich

HAWKS OPEN TALKS WITH FORMER BEST AND FAIREST

HAWTHORN has started talks on a new contract for midfielder James Worpel, as the rebuilding club looks to secure its former best and fairest winner following an impressive start to the season.

Worpel has returned to his 2019 form under coach Sam Mitchell this year, continuing his prolific campaign with 35 disposals and six clearances in the team's loss to Port Adelaide last weekend.

The 24-year-old would appeal to clubs as a strong-bodied midfielder, but discussions over an extension with the Hawks are understood to have started recently. A two-year deal would take Worpel through to free agency in 2025.

James Worpel in action during the R9 clash between Hawthorn and Melbourne at the MCG on May 13, 2023. Picture: Getty Images/AFL Photos

Worpel became the youngest Peter Crimmins Medal winner since Leigh Matthews in 1971 when he claimed Hawthorn's best and fairest in his second season in the competition at just 20 years of age.

He has since played 91 senior games, but appeared to have fallen out of favour when Mitchell took over last season only to work his way back into the side's midfield alongside Jai Newcombe, Will Day and Conor Nash this year.

Worpel has played in every game so far this season and is averaging 25.2 disposals, 6.6 clearances, 5.8 score involvements, 5.2 inside-50s and 4.3 tackles per game. – Riley Beveridge

POWER DESPERATE TO KEEP YOUNGSTER

MILES Bergman is a man in demand and Port Adelaide is pushing to retain the emerging star.

The Power are desperate to keep the 21-year-old, who has become a key part of their strong start to the season and nine-game winning streak.

Bergman hasn't been in a rush to get to his contract call as Victorian interest has grown in him across this season, with the former Sandringham Dragon moving to half-back and playing an important role for the Power.

Miles Bergman in action during the R11 match between Port Adelaide and Richmond at the MCG on May 28, 2023. Picture: Getty Images/AFL Photos

The 2019 first-round pick has played all 12 games this season after having an injury- and illness-hit 2022. 

The Power have begun early discussions on an extension for out-of-contract key forward Charlie Dixon, who is a restricted free agent this year coming to the end of his eighth season with Port Adelaide.

The 32-year-old is four games away from reaching his 200th AFL appearance and remains a central part of the Power's forward line, booting 13 goals from seven games this season. – Callum Twomey 

SWANS TO HIT MARKET

SYDNEY'S focus on securing its stars on long-term deals across the past 12 months won't prevent the Swans from being active this off-season.

Nick Blakey was the latest Swan to ink a long-term contract when he penned a seven-year extension through to the end of 2031, making it the longest current contract in the AFL.

It comes after Callum Mills (contracted until 2029) signed a six-year deal in September, weeks before Tom Papley (contracted until 2028) signed a five-year deal. Isaac Heeney (2028) inked a six-year contract at the start of last season, while Tom McCartin (2027) signed for four more during the finals. 

Tom Papley and Nick Blakey after the preliminary final between Sydney and Collingwood at the SCG on September 17, 2022. Picture: Getty Images/AFL Photos

In a season where Sydney has been hit hard by injuries at either end of the ground, the Swans are assessing some key-position options with Carlton's Tom De Koning and Greater Western Sydney's Harry Himmelberg two potential targets.

Sydney CEO Tom Harley said the club's list strategy has been focused on retaining key pieces for the long-term, but now having done that the Swans will look to strengthen its list via free agency or the trade period. 

"We've had a real sharp focus on retaining our key talent. We've gone to the draft over the last couple of years and we've built up a lot of shared experience with our 23 and under players. We need to make decisions internally on whether we think that it’s the right group and we genuinely believe it is a good group. Retaining that key talent is the first part of it," Harley told AFL.com.au.

"Secondly, you always want to look to get better. This year will be no different to other years with regards to looking to get better. There might be some different levers that we look to pull. I understand the interest in trading and free agency and I think it is a really interesting part of the game for fans. It is not as binary as what people think it is, in terms of if someone is coming off (the list), therefore there is $500,000 or $600,000 or $700,000 to spend. There is a lot of fluidity in the way contracts are structured. 

"You won't hear from me that we've got X amount and we're going to go after X player. But what you will hear me say is we've been laser focused on retaining our key talent and we want to get better and build a squad that can challenge. With trade and free agency at the end of the season, it is one of the key levers that you can pull." – Josh Gabelich

BOMBER TO WAIT ON DEAL

CONTRACT talks are expected later in the year for Essendon forward Harrison Jones as the tall goalkicker overcomes his ankle and back injuries.

Jones played the first five games this season before suffering a back stress fracture, following fellow young Bombers Nik Cox and Zach Reid in having similar injuries over summer.

The Bombers have also used the time on the sidelines to send Jones in for an ankle reconstruction after a run of injuries. 

Harrison Jones celebrates a goal during the R5 match between Essendon and Melbourne at Adelaide Oval on April 15, 2023. Picture: AFL Photos

It comes as the 22-year-old reaches the final year of his contract at the Bombers, having re-signed for two years in 2021 when he played 16 games and kicked 20 goals. 

Jones has played 31 games for the club since being drafted by the Bombers at the end of 2019. Essendon is also prioritising the signatures of restricted free agents Darcy Parish and Mason Redman while assessing the market with its salary cap cash. – Callum Twomey

SWANS EYE ACADEMY TALENT

SYDNEY has been struck by a run of injuries to its talls this season but will have first call on a young ruckman in this year's draft class.

Caleb May is a member of the Swans Academy and has been tracked by recruiters this season, with the 206cm prospect featuring for the Allies last week at the under-18 national championships.

DRAFT HUB Click here for the latest draft news

May had eight disposals and 14 hitouts for the Allies, following on from averaging 13 disposals and 33 hitouts in the Coates Talent League for the Swans Academy.

The Swans have veteran Tom Hickey leading their ruck division alongside recruit Peter Ladhams, with 2021 mid-season pick-up Lachie McAndrew recently making his senior debut. 

The club will have access to May at this year's draft as a member of its northern Academy program, and he could add a boost to their stocks of young ruck options. – Callum Twomey

Caleb May handballs under pressure from Taylor Goad during the U18 national championships match between the Allies and South Australia at Thebarton Oval on June 4, 2023. Picture: AFL Photos