Trengove has been in communication with Wingard over a potential move to Whitten Oval on a long-term multi-million dollar deal, according to AFL.com.au.
The 25-year-old South Australian is understood to be happy at Port Adelaide, however a trade would be beneficial for the Power in a year before he becomes a free agent.
The Power already hold picks nine, 21 and 27 and are likely to request pick 10 from North Melbourne for Jared Polec.
The Bulldogs will likely have to offer their first pick (currently pick six) to entice the Power to trade Wingard. Port would then have three picks in the first 12 and at least five in the top 30.
The Bulldogs will have to fight off Hawthorn, who are also admirers of the Power star.
Alastair Clarkson admitted in 2014 Wingard would be the number one player from a rival club he would like to recruit if given the chance.
Hawthorn are also hoping 2017 recruit Jarman Impey could play similar role to Trengove in their efforts to entice Wingard to the club.
Impey, Trengove and Wingard were described as inseparable during their time together at Alberton.
Port Adelaide are expected to be aggressive during the NAB AFL Trade Period, chasing West Coast free agent Scott Lycett with a four year deal.
The Power finished 10th this season, despite going on a recruiting spree in the 2017 Trade Period.