Another headache faces the Gold Coast Suns after midfielder Hayden Jolly became the second player this week to tell the AFL club they wanted to leave.
The highly-rated Josh Caddy, 19, threw a spanner in the works when he informed the Suns he wanted to return to Victoria.
Now ex-Glenelg's Jolly, 20, has told the Suns he wants to head back to South Australia.
And all while Suns staff look to cut their 46-strong roster down to 39 to make way for a minimum of three draft picks ahead of the 2013 season.
Caddy is expected to become one of the hottest properties in the AFL trade period.
St Kilda have been heavily linked with him but Melbourne and the Western Bulldogs could also come into play due to more favourable hands in the upcoming draft.
But Ashcroft said they still had not determined what would be fair compensation for the rising star.
Caddy requested a trade last year but he remained at the Suns when Essendon offered pick No.19 for his services, only to be rejected.
"We have to stand firm. We need to make sure what we're compensated for is in the best interests of our football team," Ashcroft told the Suns website.
"He's had another year of footy, he's one more year experienced, played every game (in 2012) - how do you work out what's reasonable?"
Apart from Caddy and Jolly, the two names on the Suns' lips were Maverick Weller and Josh Toy.
The out-of-contract pair appear in the Suns' sights as the Gold Coast look to reduce their roster down to 39 by October 31 to make room for their draft picks.
Josh Fraser's retirement and Nathan Krakouer's departure ensure five players must go by the end of October - and Ashcroft admitted Toy and Weller faced "nervous waits".
"We still need to make some considered calls on a few of our players that haven't been contracted," he said.
"We've taken our time and will continue to do so and get through the next four weeks so when we get to the point (trade period), we're really clear.
"We also have to give those guys the time and consideration to make sure the decision is based on the three or four years they've been here."