The 25-year-old and gun midfielder Darcy Parish are both free agents at season's end with the Bombers determined to keep hold of both.
But Redman is from South Australia, with Adelaide linked to a big bid for the dashing, long-kicking defender's services amid a season where he has averaged 468.7 metres gained and 23 disposals.
The Bombers have made an extensive presentation to Redman about the club's direction that included an appearance from Madden, the most well-known wearer of the No.27 guernsey now donned by Redman.
Madden won two premierships and four best and fairests, was captain, and booted 575 goals in 378 games for the Bombers.
"He's a famous No.27 and we'd like Redders to reach those heights in jumper 27 like Simon Madden did," coach Brad Scott said.
"But it's always interested me that clubs often make pitches to players from other clubs but don't sell the vision to their own.
"So that's a really important part of our responsibility, to be really explicit about what is it that we're building here at the Bombers and what does that look like into the future and what's his role in that?
"That's just part of a really important process for us."
The Bombers are flying at 8-5 but have made it clear they won't be rushing either Redman or Parish into a decision on their respective futures.
Asked whether the bye might have helped Redman start edging towards a decision, Scott said: "I don't know to be honest.
"We're well aware that free agency presents opportunities for players and sometimes dilemmas in terms of what's best for them.
"And I totally respect that both Darcy and Mason have got big decisions to make individually.
"And our job is to make sure that we sell a vision for our club and I think we've done a pretty good job so far of showing them the track that we're on and we've still got a heap of improvement and a lot of work to do.
"But I'm not going to go down the path of trying to coerce or emotionally blackmail either of those players into staying at Essendon. They've got to want to stay for the right reasons."