Essendon are reportedly prepared to have a sizeable contract offer ready to acquire St Kilda free agent Jade Gresham via the Pre-Season Draft if needed.
The Bombers are set to submit the required paperwork for a move to acquire Gresham no later than today, with the Saints then weighing up whether to match the bid for the restricted free agent and to enter trade discussions for the South Morang junior.
St Kilda are prepared to retain the half-forward if a move fails to transpire, but the threat of Essendon allowing Gresham to walk to the Pre-Season Draft looms as a potential avenue the Bombers could pursue if the Saints look to force a trade.
According to News Corp, Essendon is ready to offer Gresham a front-ended offer that would likely outbid clubs like Hawthorn, who are ahead of them in the Pre-Season Draft order.
The Bombers would prefer to sign Gresham before Friday's 5:00pm (AEDT) free agency deadline, though, while St Kilda could view the return of compensation for the 26-year-old as the safest outcome despite the uncertainty surrounding the value of the draft selection they'd receive in return.
Gresham's move could land the Saints band two compensation and, therefore a late first-round pick, while a second-round selection is also likely in play.
If the Saints do decide to match a bid and hope for a trade with the Bombers, the former could walk away with nothing given the opportunity that the Pre-Season Draft presents for the Dons.
A similar move was made by Carlton in 2019 for outgoing Gold Coast midfield-forward Jack Martin, with the Blues allowing him to walk to the Pre-Season Draft and sign the Western Australian.
Carlton forked up a heavily front-ended deal for Martin that would've been hard for rivals to match, with that contract now having the 28-year-old on a much lower salary as it nears its expiry.
News Corp's report suggests the Bombers aren't keen on trading for Gresham and sparking negotiations between popular list figures Adrian Dodoro and Stephen Silvagni, hence why the Pre-Season Draft threat looms.
Essendon already needs to resolve a move for departing defender Brandon Zerk-Thatcher to Port Adelaide and in return, could land Power wingman Xavier Duursma.
Young flanker Massimo D'Ambrosio is also on the way out, looking to land at Hawthorn after just 18 months at Tullamarine.
Gresham looms as the third and final free agency target Essendon has lined up for this off-season, having already added North Melbourne pair Ben McKay and Todd Goldstein this week.