When it comes to doing it tough ahead of the start of a new campaign, the former Town manager encountered a situation far, far worse than the one which greets Jan Siewert following the Terriers’ painful Premier League relegation last term.
Jackson, a match-day regular at the John Smith’s Stadium as part of the club’s commercial team, can still vividly recall those days in the summer of 2003.
His second coming as Terriers chief saw him handed the reins at a club just out of administration.
Earlier that year, fears had been abound that Town could even disappear amid debts of nearly £20m.
The number of professionals who greeted Jackson at the start of pre-season was comfortably under ten. But a special story soon began to emerge.
Fine young professionals including the likes of Jon Worthington, Andy Holdsworth and Jon Stead were complemented by solid signings of stature in the shape of Efe Sodje, Steve Yates, Tony Carss and Rob Edwards and the blend proved an intoxicating one as Town immediately jumped out of football’s basement.
Now as then, Town must re-align and construct a new side. It is a challenge, but a wholly difference one, with a number of stalwarts from the last three seasons and more recent high-profile signings likely to depart, with others assigned with stepping out of the shadows.
Jackson, for one, knows which is the more straightforward task. He told The Yorkshire Post: “When I arrived back, there were six players turning up for pre-season. Now, they have everything in place; the training ground, the stadium and the fanbase.
“We were going to Mansfield and Cheltenham and, in the last few years, Huddersfield have gone to the likes of Manchester United and Chelsea, so it is a massive difference for a club to go through those changes.
“But it has been all for the good and it has put Huddersfield firmly on the football map, globally.
“They deserved to be there and, hopefully, there will be more good times ahead, so we can start getting back to the likes of Old Trafford.”
On the season ahead, he continued: “People may think the club should be challenging to go straight back up, but I think it is going to be a difficult season.
“Behind the scenes, there have been big changes with Dean (Hoyle) stepping down and the new chairman coming in and it is a brand-new start and that is the way they have to look at it.
“It is exciting, but it is a season which could go either way.
“For me, the recruitment is key for them – a really big key if they are to do anything or mix it.
“I looked at the first year and thought they may stop up in the Premier League. But in the second season there, the recruitment in the summer was poor.”
Just as Sodje, Yates and company helped pull the club up by the bootstraps on the pitch during that epic 2003-04 season which ended in promotion glory after a famous penalty shoot-out play-off final win over Mansfield Town, so Jackson is looking for the leaders to emerge in the present-day Huddersfield line-up.
In his eyes, there was a vacuum in that regard amid a bruising and morale-sapping season when confidence tanked from a Town side punch-drunk from taking heavy punishment in a seemingly endless run of winter losses.
For the Terriers to successfully rebuild, new leaders must step forward, with the club’s canny addition of a seasoned head in experienced centre-back Tommy Elphick one potentially key piece in the 2019-20 jigsaw, according to Jackson.
“In my second spell there, I signed Efe Sodje and Steve Yates. There were two real characters,” said Jackson, one of the Town legends on duty whom supporters will be able to share company with on a match-day as part of the new ‘Legends Club’ hospitality package.
“They had their off-days, but in general, they would give you everything and you need leaders in your team. I think Huddersfield lacked a bit of leadership last year. They need to bring in some strong characters as there will be some expectation to be challenging to go straight back up.
“The spirit within the club got them in the Premier League and kept them in it in the first year.
“But they lacked a little bit of that last season and will be looking for more key characters and to see the desire, spirit and will to play for a good club.
“I like the signing of Elphick. He is a good solid Premier League player who has been there at some big clubs and knows what it is all about in the Championship and all the indications for me are that as a first signing, it is a very good one.”