Money in the bank is all well and good, but keeping 'customers' happy is integral to any hope of further success in the future.
It therefore comes as some surprise to read Ashley's latest plans for Newcastle United.
Visit any home game on Tyneside this term, or last for that matter, and you get a pretty clear sense that Ashley is public enemy No. 1 at St James' Park.
Apparently, though, the Sports Direct mogul appears to think that a one-fingered salute and a barrage of four-letter profanities is a sign of endearment.
Why else would he have come to the incredible conclusion that retaining his stranglehold on the Magpies is best for all concerned?
Ashley has spent the best part of 18 months trying to shift the club, dropping his asking price in a manner more befitting of a second hand car salesman than the owner of a professional football club.
There have been a few tentative bites on the line he has cast but he has found few parties willing to match his £100million valuation of a struggling Premier League, and now Championship, side.
There is something to be said for sticking to your guns, but in this situation his stubbornness is causing nothing but anger and frustration to those tired of following the Newcastle circus around the country.
Many of the Toon Army would happily sell their own grandmother if they thought they could get enough for her to buy Ashley out, but the truth is that raising funds in the midst of an ongoing recession is not easy.
Unfortunately for Magpies fans, the cash crisis gripping the global economy appears set to leave them unable to awake from their Ashley-dominated nightmare.
He has come out and said that he now has no intention of selling the club and is happy to stay put and attempt to build bridges with those he has alienated.
This appears to be the most wishful of wishful thinking if comments to skysports.com from Newcastle fans are anything to go by.
Joke"Quite simply a joke, a joke manager, a joke owner, and the only thing that is not a joke is the mess we are in. How on earth can't people see past this situation?" Magpies supporter Craig Buglass sums up the feeling on Tyneside.
But, things get worse.
As if Ashley's announcement that he has unpacked his bags and is now set to stay did not cause enough unrest, the revelation that he is now looking to sell off naming rights for St James' Park has proven to be the final straw for many.
Newcastle have played their home games at the iconic ground since 1892 and it is one of the most recognisable venues in the country.
For Ashley to even contemplate devaluing its heritage by plastering advertising eye sores and neon lights all over it has a number of Magpies followers on the verge of spontaneous combustion.
"If Ashley re-names St. James' Park it will show an absolute disregard to the history and the fans of the club. I know that the modern world is all about money especially to businessmen like Ashley but there are things that are taboo and this is one of them, leave well alone Mr. Ashley." - Alan Rowe.
"Rename St James' Park? After all of the major errors that Ashley has already made, for me, this is the most unforgiveable. I know it doesn't make any difference to what is happening on the pitch with the team etc. but our 'home' will always be known to fans as St James' Park. This guy just seems to make error after error after error and continues to plumb new depths." - Ross Patterson.
"Renaming the stadium is absolutely disgusting. It will totally diminish from the history of the club that makes it what it is. I am in absolute shock and I think the majority of Newcastle fans will be as well. Ashley has not had the best of times at Newcastle and I think this is just going to add to the already bad relationship between himself and the supporters." - Rory Davies.
They - whoever 'they' may be - say things often come in threes and the Ashley saga is no different.
To add to the decision to fly in the face of adversity and retain his post as club owner, and the questionable naming rights proposal for St James' Park, Ashley has also opted to take the easy, and cheaper, option when it comes to resolving the managerial situation at Newcastle.
The club have been without a full-time boss since Kevin Keegan's acrimonious departure in September 2008, with Joe Kinnear, Alan Shearer and Chris Hughton taking the reigns on an interim basis.
Supporters had hoped that the delay caused by on-field troubles, which ultimately resulted in relegation out of the Premier League, would eventually make way for a big-name appointment.
CoachUnfortunately, those dreams have been dashed by the decision to hand Hughton the post on a permanent basis.
Few are doubting the coaching credentials of the affable Londoner, but he has no prior experience of such a role and the feeling around Tyneside is that he is not the answer to the many questions which have been raised over recent years.
He should have enough quality at his disposal to lead the Magpies back into the big-time this season, but there is a feeling that he will soon fall the same way as many of his predecessors as soon as Newcastle reacquaint themselves with the Premier League.
"I thank Chris Hughton for the job well done so far but don't think he can cut it in the Premiership." - Mark Conroy.
"He (Ashley) has now appointed Houghton as manager, he is not a manager, he is a coach. The team is not playing good football and he is picking the wrong players for me. We need someone quick up front but we haven't got anyone so we just knocking it long for Carroll, Ranger or Harewood. He should have appointed Shearer at end of last season backed him with the few players he wanted and I am sure we would of been running away with this league, not dropping points against poor teams" - James Raine.
"No, no, no, no. Hughton as manager now, no! If he kept up a good job and was still top half by halfway through the season, maybe then Hughton for manager. I fear for him. And as for Ashley staying, is the £20million to keep the supporters happy? Where did he get that from? I know so many supporters who won't step foot in the ground as long as he is there, and I'm sure there are many more that feel this way! And please Ashley for your own sake don't rename St. James Park!! The rest of this season could make or seriously break Newcastle United." - Richie Cange.
All in all, Newcastle's hopes that time spent away from the glare of the top flight would enable them to establish some stability, get their house in order and return better prepared for the task in hand have come unstuck in spectacular fashion.
The Magpies are incapable of avoiding mass hysteria, which is detrimental to performances on the field, alienates the fans and generally tarnishes the image of a once great club.
It is difficult to see where they go from here. With Ashley seemingly going nowhere any time soon, the undercurrent of discontent will linger on and problems will continue to arise.
Promotion may paper over a few cracks, but rips will inevitably appear as soon as something goes wrong and the club's long-suffering supporters will be right back at square one.
I for one do not envy them and the circumstances they are forced to deal with, and I think it is fair to say that the majority of neutral fans across the country take one look at the ongoing troubles and think to themselves that as bad as things may be at their own club, at least they are not Newcastle.