In two years with the Whites the full-back learned the hard way how fortunes can fluctuate in football.
From being one of the first names on Phil Parkinson’s team-sheet and aiding a last-day Championship survival bid against Nottingham Forest, the 30-year-old somehow became the dressing room’s nowhere man, a peripheral figure lost in a second season of financial turmoil.
Little is one of a squad-full of players who have not been paid properly since February but with just four appearances last term, rarely even had the escape of matchday to channel his frustration.
As he signed a contract to play for one of Wanderers’ League One rivals, Bristol Rovers, next season, the defender summed up the difficulty which will face the club’s next owners as they look to patch-up a squad this summer and a sense of resentment still harboured by a team who felt abandoned by its employers.
“I don’t think the players are necessarily angry anymore – we’re just sad,” he told The Bolton News. “The whole situation just makes your heart ache.
“I don’t feel like I have walked away at Bolton, more that I’ve been forced out. You just can’t predict what is going to happen there.
“Even if they find a buyer within the allotted timeframe it’s going to be panic stations. And as a footballer coming out of contract you need to make sensible decisions for your career and for your family. You can’t do that over the course of a week.
“All clubs want to get their squads pretty much sorted by pre-season but if I hadn’t agreed something with Bristol Rovers there were no guarantees what we’d have back at Bolton.
“There might be a magic wand, I dearly hope they find an owner who can turn the club around and make things better again because the fans deserve that, but you could just as easily find yourself in the same situation.
“When I signed at Bolton I felt they had been playing in the wrong division, League One, and they were on their way back up. Now, it might take time to get to that position again, and I just hope it doesn’t all go south.
“I might be willing to gamble my fortunes on a decision like that but I won’t do that to my wife and son.”
Players at Wanderers will not receive a pay cheque until such time as a new buyer in found, which Little reasons has left some in a vulnerable financial situation.
“I have always been taught to have an emergency fund on one side, just in case the end of the world happens,” he said. “Three months’ worth of wages, just in case. And I was running short – so you can kind of work out where I am at.
“But not everyone does that, not everyone can. I have got on with things and signed elsewhere but there are definitely lads, how they are going to function I just don’t know.
“We had plenty of meetings to discuss what was going on but how tough would it be to come out and say you were struggling in front of your team-mates? I don’t think I’d have felt comfortable.
“I believe some of the lads have spoken privately with senior players in the dressing room and been offered some help.
“We all spoke regularly, all met and voted to decide what our next plan of action would be – but it is difficult to make a decent decision unless you know exactly what is on the table.
“All this is from my point of view as a player. Non-football staff must be 10 times worse. To be talking about food banks at a football club is just awful.”
Little has no doubt as to where Wanderers’ hierarchy failed in their duties off the field for the last 12 months.
“Communication was the big thing,” he said. “When I play for a manager I want him to be doing everything he can to make sure I’m running through brick walls for him.
“And when I play for a club, I want them to value me as a person and as an asset that they have invested in. But neither of those things happened.
“The only information we got was through the paper. I just don’t understand how you can be working for someone, making them money, and yet they don’t have the common decency to send you an email to tell you what is happening.
“They say it’s a need to know basis and apparently we, the players, didn’t need to know.”
After taking some time to find his feet at Bolton, the former Bristol City man secured a regular spot and seemed to have captured fans’ imaginations with his energy on the right flank by the time Wanderers beat the Robins 1-0 at the UniBol in February last year.
Indeed, he was being tipped as a potential player of the season prior to a red card against QPR the same month, which completely derailed his Bolton career.
Post silly lunge at Loftus Road, Parkinson opted to play Fil Morais as a wing-back and, eventually, loan signing Jon Flanagan, leaving Little to pick up scraps for the final few months.
“They didn’t play me or pay me in the end, I suppose,” he said, attempting to make some light of difficult subject matter.
“That first season I felt I was playing well, playing regularly. And if you look at the stats, I think we won 11 games that season, and I played in the vast majority of them.
“It was strange because I didn’t play at first when I walked through the door and it was only in the middle part of that season that I really felt comfortable.
“But I believe in the end I played a big part in us staying up that season and when I came back in the summer I was looking forward to pushing on.
“The manager said I was fitter than I had been the previous summer but then he signed Pav (Pawel Olkowski) and that was that.
“I’m not angry, I’m not going to start moaning and groaning, I was just gutted that the move hadn’t worked out.
“I grew up in the same youth team as Mark Davies at Wolves and when he got that move to Bolton I thought ‘I’m never going to play for a club like that.’ When it happened, it was a genuine honour. Nothing that has happened at the club will change that.
“I was in the right league, playing regularly and then it just stopped. I was confused more than anything else.”
Little was offered a chance to leave last December, shortly before the financial ceiling well-and-truly fell in at Wanderers but opted to stay and fight for his place.
“The manager said if I wanted to go out and get more games, find another club, I could. But I honestly looked at the team and thought I was getting back in there,” he said.
“We were losing games left, right and centre, so I was thinking ‘surely he has got to put me in at some stage?’ And at that point I wanted to kick on.
“I’m confused why that wasn’t the case but that’s life.”
In all, Little made just 35 appearances for Wanderers, although he leaves in the rather unique position of being a player whose reputation remained untarnished by last season’s mediocre performances on the pitch.
“The fans were awesome – from the moment I walked through the door I have had nothing but support from them and I really do thank them for it,” he said.
“I haven’t had a bad word from them in the two years I have been there and there’s not many clubs that kind of thing would happen at.
“For that reason, as much as anything else, I’m sad to leave.”
Little’s next career move throws up a whole new set of difficult circumstances.
As a player steeped in league and cup success with Bristol City, eyebrows have already been raised that he will now be wearing the blue of their arch-rivals.
Striker Matt Taylor broke the taboo, becoming the first player to transfer directly from Rovers to City in three decades in 2017. For his troubles he had to deal with breeze blocks through his car window, death threats over the phone and an inability to drink in bars on his own doorstep.
“It’s something I’ll have to deal with,” Little said. “I know Tayls and he got through. It was horrible at first because he’s Bristol-born-and-bred but I’m not a 20-goal-a-season man, so I might get away with it.
“I did my bit for City in the past but I genuinely want to go and do the same at Rovers.
“There might be a few idiots, who knows, but sat here right now I’ve had quite a lot of supportive messages.”
With a population just shy of 450,000, Bristol is the largest city in England never to have hosted a Premier League team. And though the Lee Johnson and Dean Holden’s Robins have been knocking on the door for the last two seasons, Little is optimistic ‘The Gas’ can make their own claim eventually.
“I think it’s an untapped resource,” he said. “They always chanted ‘there’s only one club in Bristol’ but I’m telling you now, Rovers can move up a level.
“I was lucky enough to be part of some great times with City, got promotion from League One, so why can’t that be the case again?
“Last season there were six or seven clubs who were strong and I think it’ll be the same again – although there’s no telling what Bolton will be like.
“As for the rest, there’s nothing between them. So why not have a tear-up? I’m ready to challenge for the play-offs.”