Will this difficult decision to allow the 28-year-old to join Tottenham – after 10 years of outstanding service at Molineux – be the platform for evolution and even better things?
Or, a few years down the line, will this be a move that is looked back upon with a great deal of regret?
Well, all we know for now is that the next several weeks are massive for Wolves as they look to sustain the success of recent seasons.
Big business simply has to be done. Not only to replace Doherty, but to keep Nuno Espirito Santo – whose current contract expires next summer – happy, and capable of taking the team to the next level.
Assessing the Irishman’s £15million move to North London, the fee has underwhelmed a fair few Wolves supporters.
Understandably as well, given his consistent, high-level performances in both the Premier League and Europa League. He has been fantastic.
But there are a few things to factor in. Doherty, despite how brilliant he has been for Wolves, is not the most glamorous of names in the wider footballing world.
His age means there is not much sell-on potential for Spurs, and Doherty is understood to have wanted a fresh challenge – while another thing perhaps worth considering is that Jorge Mendes is his agent.
Whichever way you look at it, though, Wolves must be confident that it’s enough to make the required reinforcements.
They are now without both of the first-choice wing-backs of the past two seasons, with Jonny Castro Otto set to spend months on the sidelines with a knee injury.
So, they must be confident about getting fresh faces in soon. They will have irons in the fire, and now it is firmly about getting players through the door.
There is a fair amount of frustration among fans, with many upset at losing someone who has played such a pivotal role in getting Wolves to where they are now.
Others are more accepting of the situation, feeling Doherty may have reached his peak and that now was the right time to cash in.
Either way, the onus is on acting quickly and effectively.
The club may have until October to get things sorted – but it is still a race against the clock. Hopefully, this proves to be another shrewd call. Let’s see how it goes.