For Richmond, that time is right now in its dealings with full-forward Jack Riewoldt.
The two-time Coleman medallist does not want to leave the Tigers, but the fact is he is yet to re-commit after months of negotiations.
And the Fremantle approach is significant, at least $200,000 a season more than what Richmond has tabled.
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Just as there comes a time for a club to pay overs to keep a player, there also comes a time for another club to offer way overs to attract that same player.
The Dockers went extremely hard at Travis Cloke last year. Equally as hard and unsuccessfully at Harry Taylor this year.
They know they are thereabouts under Ross Lyon's control, but, clearly, they have determined that a premiership could come far easier with a marquee forward on their list than it may without one.
What if the Dockers have actually upped their offer, from $850,000 a year to say, $950,000 a year since Taylor officially said no? Or more? That would make things very interesting, in light of Richmond's offer of about $600,000 a season.
Luke McPharlin, Matthew Pavlich and Aaron Sandilands may have just one season remaining in their grand careers. They would be firmly behind their club's pursuit of Riewoldt.
What price a flag for that trio? Surely they would even consider altering their current deals if it meant squeezing Riewoldt in.
And what price a flag for Lyon? He is the best coach in the competition. But he hasn't won a premiership.
He's not one to look back in life, but he knows he baulked, at the very last minute, at recruiting Ben Cousins at the end of 2008. Some St Kilda people still believe to this day that had Cousins been part of the Saints' line-up in 2009, the Grand Final would not have been lost to Geelong.
Lyon will not die wondering on this.
Tigers' footy operations boss Dan Richardson boasts nous as sound as anyone in football. With his background as a high-end player manager, he knows the AFL market.
It would go totally against his beliefs to offer Riewoldt more than his club could afford, but he would be well aware he now has to do just that.
The risk, of course, with such an approach is potentially losing another player, and with Dustin Martin and Reece Conca also requiring fresh Richmond deals, things will be extremely tight.
But Martin, as brilliant as he is, and Conca, as promising as he is, are not worth as much to Richmond's future as Riewoldt.
By way of comparison with Riewoldt, they are replaceable. Riewoldt is not.
Any temptation - even if it is as low as a 10 per cent chance - that Riewoldt or his management may be peeking sideways at the Dockers' offer, must be removed by Richmond.
Before the finals.
Twitter: @barrettdamian
Just as there comes a time for a club to pay overs to keep a player, there also comes a time for another club to offer way overs to attract that same player.
The Dockers went extremely hard at Travis Cloke last year. Equally as hard and unsuccessfully at Harry Taylor this year.
They know they are thereabouts under Ross Lyon's control, but, clearly, they have determined that a premiership could come far easier with a marquee forward on their list than it may without one.
What if the Dockers have actually upped their offer, from $850,000 a year to say, $950,000 a year since Taylor officially said no? Or more? That would make things very interesting, in light of Richmond's offer of about $600,000 a season.
Luke McPharlin, Matthew Pavlich and Aaron Sandilands may have just one season remaining in their grand careers. They would be firmly behind their club's pursuit of Riewoldt.
What price a flag for that trio? Surely they would even consider altering their current deals if it meant squeezing Riewoldt in.
And what price a flag for Lyon? He is the best coach in the competition. But he hasn't won a premiership.
He's not one to look back in life, but he knows he baulked, at the very last minute, at recruiting Ben Cousins at the end of 2008. Some St Kilda people still believe to this day that had Cousins been part of the Saints' line-up in 2009, the Grand Final would not have been lost to Geelong.
Lyon will not die wondering on this.
Tigers' footy operations boss Dan Richardson boasts nous as sound as anyone in football. With his background as a high-end player manager, he knows the AFL market.
It would go totally against his beliefs to offer Riewoldt more than his club could afford, but he would be well aware he now has to do just that.
The risk, of course, with such an approach is potentially losing another player, and with Dustin Martin and Reece Conca also requiring fresh Richmond deals, things will be extremely tight.
But Martin, as brilliant as he is, and Conca, as promising as he is, are not worth as much to Richmond's future as Riewoldt.
By way of comparison with Riewoldt, they are replaceable. Riewoldt is not.
Any temptation - even if it is as low as a 10 per cent chance - that Riewoldt or his management may be peeking sideways at the Dockers' offer, must be removed by Richmond.
Before the finals.
Twitter: @barrettdamian
