St Kilda coach Scott Watters says free agency rules have led to an 'awkward' situation as the club attempt to re-sign star utility Brendon Goddard.
Goddard will become a restricted free agent at the end of the season and has been linked to several clubs.
The Saints announced the re-signings of Lenny Hayes, Stephen Milne, Sam Gilbert and Leigh Montagna on Wednesday, before young gun Arryn Siposs also put pen to paper on a new deal on Thursday.
Despite contract talks with Goddard and his management continuing to drag on, Watters said he was still confident the 27-year-old would stay.
"I'm confident and really optimistic. He's a really committed Saints person. It's a challenging time for Brendon," Watters said on Thursday.
"It's a different situation that AFL players haven't been used to or exposed to. It's an unenviable position in many ways but I believe he will be at this football club.
"We think we've put a really strong offer to Brendon. His importance to the club going forward - he's integral to it.
"But under the new system he has an opportunity to test the market so it's irrelevant whether I like it or not that's the situation and I support the whole concept.
"But it can be awkward sitting there as a coach whilst you're within that concept as well."
Watters was quick to praise the five players who re-signed earlier in the week, highlighting their desire to stay at the club ahead of earning more money elsewhere.
"One thing I'll say about all these guys is they're not playing here for the money. They play here because they love the club," he said.
"The negotiations were pretty quick to be honest because they want to be here and we want them here. They're really valued people (and) valued Saints people."
The Saints take on Carlton in a dead rubber at Etihad Stadium on Sunday, with the two teams playing for ninth spot.
Watters said he had sympathy for sacked Blues coach Brett Ratten, adding he was unsure whether Carlton would lift for their outgoing mentor.
"There's a lot of myths about that exact situation," he said.
"Sides can come out and play well, sides can come out and be really flat ... but we just focus on what we need to do."