Judd's management have said they will fight the League announcement on Friday that his long-time agreement with recycling giant Visy could no longer exist outside club Total Player Payments.
The lucrative ambassador role is understood to be worth about $200,000 a season.
"It's certainly very disappointing from our point of view and makes it very difficult to cultivate a career post-footy and explore work opportunities while you are playing," Judd told Channel Seven.
He added the "goal posts are constantly being moved".
The AFL say they flagged two years ago that the rules surrounding third party deals would be tightened with the advent of free agency.
Malthouse, who is with Judd and his teammates at a pre-season camp in Arizona, was also unimpressed.
"When you start changing the rules halfway through, I'm just astounded," Malthouse said.
"I don't think it's fair on either (Judd or Carlton) or any other player in the competition.
"The league may be painting themselves into a very, very dark corner."
