In his most recognisable role as a Gillingham stalwart, Andy Hessenthaler straddled the line of veteran player and young manager in the second tier. Now leading his fourth club at Eastleigh, the ever-combative midfielder of yesteryear is the same as he always was when he joins the action in training, but almost 18 years on from first taking to the dugout, he realises the landscape around him has shifted.


Eastleigh FC


Andy Hessenthaler has been a distinctively familiar name and figure in English football for some time now and what will always feature chiefly amongst any summary of his achievements is his impact at Gillingham. The Dartford native captained the club, has come out on top in polls of the greatest Gills player, and he even managed them in three spells, twice of which had him in sole charge.

His part in Gillingham reaching the old First Division (or the old, old Second Division) for the first time in the club’s history enjoys an exclusive spot in his affections. Bouncing back from the famous 1999 Division Two final loss to Manchester City to be in the playoffs again in 2000, this time under Peter Taylor instead of Tony Pulis, Andy would have a pivotal say.

The Gills had the chance to go up on the last day before being beaten 1-0 by Wrexham, but they would get to celebrate in arguably much better fashion in the last set of playoff finals under the Twin Towers of the old Wembley. As he had in the semi with Preston North End a year earlier, Andy’s scoring touch proved crucial, as he struck in sensational fashion at Stoke City in stoppage time of the first leg.

Finding the top corner from outside the box with his right, the effort in front of the Gills fans meant they returned to the Priestfield Stadium with only a 3-2 deficit. Ultimately seeing off the nine-man Potters 3-0 after extra-time, they would avenge the ‘99 final in memorable fashion.

Wigan were the opponents, and after a 99th-minute Stuart Barlow penalty had given them that sinking feeling again, Gillingham came back to lead 3-2 through Steve Butler and Andy Thomson in the final few minutes of extra-time. Having relinquished a 2-0 lead in stoppage time of the previous year’s final, ‘surely Gillingham aren’t gonna throw this away now’ were the words from the Sky Sports commentary – and they didn’t.

It ended with Adrian Pennock and Paul Smith lifting the trophy after that climb up the Wembley steps and it was a huge peak in an era of Andy’s career that he remains most closely associated with, as both player and manager. Featuring alongside the likes of Nicky Southall, Guy Butters, Junior Lewis, Carl Asaba and Iffy Onuora, the present-day significance to Eastleigh is that the mark of those days has its lasting imprint on Andy and how he operates.

As well as what they were able to bask in together as players, he remains especially grateful for how that crop of characters helped him carve out the very beginning of what has been a sustained football life after playing.

“I’d say without a doubt they’d be the best, 100 percent,” the former Watford midfielder began. “It was pretty much week in, week out, and day in, day out in training, where we knew what we were going to get from each other.”

“I was fortunate enough after the Stoke game and after we went and beat Wigan that I was given the opportunity to take over as player-manager after Peter Taylor left. That group, they managed themselves; they made it so much easier for me to make that transition.

“It was frightening really. Without a shadow of a doubt, though, the team spirit, we were a collective on the pitch, and off the pitch we used to socialise as a group as well.

“That’s with families as well, and I’ve never seen that since really. I think it would be lovely to be able to bring that back into football, but I think it’s hard to do that now.”

There are some parallels in the group at Eastleigh, with League experience all through the squad, though it is fair to say it has been a bumpy ride for those involved at the Hampshire club this season. Former Leyton Orient and Dover Athletic boss Andy was brought in as assistant to a valued friend of his in Richard Hill last April, having left Orient in September 2016 in just one of many parts to what has been a tumultuous-to-bizarre era in the renowned club’s history.

At Eastleigh, it is an outfit that has had Chris Todd, Ronnie Moore and Martin Allen all spend time at the managerial helm since Hill ended his three-year reign in September 2015, but he returned last February as director of football and caretaker manager. This season appeared to be taking its toll on all concerned, with promotion designs seemingly replaced by thoughts of mere consolidation, and Hill moved back into his DoF role just before Christmas, with Andy stepping up to become gaffer.


“It’s an exciting club to be at, to be fair. The infrastructure’s fantastic, the chairman knows what he wants and there’s a good fanbase here.”


That was a move that ex-Whitehawk boss Hill said had always been the plan, though they had hoped it was to happen with the side in a stronger position. Andy had seen it all up close as assistant but admits that when he took over he had an even greater appreciation for what Hill had been having to juggle – ‘player accommodation, all sorts.’

Seven without a win in the Vanarama National League, Eastleigh then started his tenure with a 2-1 win at Dagenham & Redbridge, showing resilience after falling behind that had been sorely lacking up to that point. Two draws and four wins in a row followed, but the last four in the league have been more challenging, with three losses before the goalless draw with FC Halifax Town last time out.

The Spitfires share a league record for most draws with Wrexham (15), which has hampered their play-off hopes. Under Andy, though, they managed back-to-back wins for the first time, while the Halifax clean sheet was their first in 27 league matches, and he sees plenty of cause for optimism as they sit 13th.

“Yeah, I mean obviously when I came into the club I was coming in as assistant to Richard, and like you said, the first part of the season we had too many draws. In the end, Richard decided he wanted to make the move upstairs and give me the opportunity, which was great.

“It gave me an insight the first few months, about the football club, and it’s a fantastic group of players here, a fantastic club. We’ve just got to get that real consistency within the group to actually push them on.

“We’re pretty much just playing catch-up now; we’ll need to do an awful lot to reach that last play-off place, but there’s a lot of positive sides over the last few weeks. It’s an exciting club to be at, to be fair.

“The infrastructure’s fantastic, the chairman knows what he wants and there’s a good fanbase here. Hopefully I can be part of making them successful.”

One noticeably heartening development after Andy took up the role was the upturn in form for the experienced Chris Zebroski. The former Millwall and Torquay United frontman scored six goals in the first month of his tenure after only scoring once all season before that.

Among the campaign’s struggles has been having to contend with the long-term loss of another source of goals in Reda Johnson, who was an unusually-prolific Championship defender not all that long ago for Sheffield Wednesday. The buccaneering competitor has often struggled with injuries and has only just returned to playing for the Spitfires, figuring in their most recent match, with FC Halifax.


“It is a good dressing room; they’re very much together. I think that might have been questioned a few times.”


Johnson’s return is a huge boost, with the obvious hope that the Benin international, who was a huge favourite at Wednesday, can steer clear of setbacks to greatly aid Eastleigh. The 29-year-old is just one of the experienced names in the ranks alongside the likes of ex-Arsenal keeper Graham Stack, one-time Watford winger Mark Yeates, and several others.

As he alluded to, Andy has been around that kind of dressing room before, so does having so many experienced voices in there bring its own challenges for a manager, or is it very much a help rather than a hindrance?

“It makes my job easier, with the group of players we’ve got, because we’ve got a lot of experience in the dressing room. It is a good dressing room; they’re very much together.

“I think that might have been questioned a few times. When you lose games, people question that, but I work with them every day and there is a good group.

“You can bounce things off the likes of the Ryan Cresswells and Sam Togwells who’ve been in the League, Mark Yeates. It does make my job easier that they do manage the dressing room themselves.

“I think once you leave that dressing room as coaches, you know we’re in good hands in there because they’ve been there and done it, but they also know this is a tough league.”

Together with the high points like promotion with Gillingham and keeping them in the second tier, winning two successive promotions with Dover to take them up into the National League South is a feat that sits proudly on Andy’s CV. There was also the undoubtedly admirable achievement of playing into his 40s at a good level, as he continued to make his mark as an unerring bundle of competitive spirit, and as we have seen plenty of times down the years, ability to supplement it.

The tough times have certainly been there too, not least in the beginning when he was let go by Charlton as a youngster. As he will cite during the regular Q&A section of this feature to finish, though, that ultimately set him on his way to a pro career which began at Watford as a 26-year-old, as he remained true to the words of his late father, himself a one-time footballer.


Andy in 2009 during his days at Dover Athletic, where he played and managed with success. Photo: ChrisTheDude at English Wikipedia


As he reflects on spells through the years that have tested him beyond simply the rigours of a match day, Andy recalls some advice given to him by a current Premier League manager that continues to help him today.

“You do have to drag yourself through, and I have had periods of that and it’s very tough. Football’s great when you’re winning games, but I’m one of these people now where I’ve learned that you don’t get too carried away when things are going really well, because it can easily change.

“It was funny because when I was the Gillingham manager and I did a bit on Sky with David Moyes, he was Preston manager and we’d played against them a few times and he then got the Everton job, and when we were on our own he said, ‘I’ve gone from Preston where I’ve had to do everything, and now to Everton where it’s all done for me. But one thing I did learn when things weren’t going well at Preston was to give yourself a day off.’

“It was good advice really because I never used to give myself that day off. I lived in Gillingham, it was on the doorstep, so whenever players did have a day off, I never switched off.

“I think that’s one thing I’ve learned when things aren’t going well, to give yourself a day of recovery and have a bit of time with your family. It was good advice from David, to be fair, because ever since then I’ve done that.”

Back on that May 2000 afternoon, Andy’s son Jake walked out as a mascot with him at Wembley. Now the 23-year-old is part of the modern era of the game, as a Gills midfielder himself, working with his father and Peter Taylor at the club during his earlier career.

Prior to stepping down in late-2004 with Gillingham still in the Championship, Andy had established himself as a player-manager at that level over four seasons. Although it seems like just yesterday to many of us, much has changed in football and in a societal sense since the beginning of the century.

Andy offers his take on how the complexion of the game and what the life of a manager entails is different to when he started in the dugout.

“I think the demands have changed. I think social media’s a big part; when I was at Gillingham as manager there was social media, but not as strong as it is now.

“You pretty much can’t get away from it. Again, going back to some of the darker days, it’s tough because it’s highlighted a lot when things aren’t going great and it’s all over social media.

“I’m one of these people who doesn’t do social media; I don’t do Facebook, don’t do Twitter, and I never will do, but that’s where the game’s changed in terms of the media side of it. I think the game has changed, players have changed, I’ve got to say.

“I think players are a lot more spoiled now than they were when I was playing; they get so much given to them. Is that a good thing?

“I think sometimes it’s not a good thing. Do they appreciate it enough?

“I’m not sure they do. I think that’s one of the things I’ve seen over the years; where football’s changed and it’s more about business now.

“That’s what it is and we’ve had to move with the times. Managing players is difficult.

“I think your man-management skills are really important and your hardest part is that you’ve got to leave good players out. You have to do it, that’s your role, but that’s part of the job perhaps I don’t like.”

Eastleigh’s chairman Stewart Donald, currently over six years into his tenure, admitted last month he had ‘got carried away in the past’ trying to get the club into the EFL. He told how a more frugal approach was necessary, even if it has recently seen them miss out on players due to wage demands, but the long-term ambition of all involved remains just as it was.


“I’m excited for the future, I really am.”


As for Andy, while his work continues, the impact he had on the field remains. So too do the friendships, with ex-Gillingham midfield counterpart Nicky Southall, also in the division as Maidstone United’s assistant, one such example.

Prior to arriving at Eastleigh, he got to lift another trophy, in England colours in the Seniors World Cup in Thailand in 2016 and again in 2017 with Harrogate Veterans. The euphoric moments from his playing days go together with the lighter-hearted ones that are just as valuable in their own way.

There are few better examples of that than in September 2003 when Andy was sent from the dugout in Gillingham’s match with Cardiff City at Ninian Park, only to re-emerge to Bluebirds boss Lennie Lawrence’s amusement as he came on as a sub – he was player-manager after all! One thing you could always count on was the kind of whole-heartedness that will always resonate with supporters, and that desire is just as present today, as he continues to search for the right pieces to ultimately take Eastleigh on towards a prosperous EFL tomorrow.

“I’m excited for the future, I really am. It’s a really good football club and I’m enjoying my life.

“I love managing, I love coaching; I’m a manager that likes to coach, not just manage. Some managers leave it to the other coaches on the training ground but I coach and manage with the same enthusiasm as when I used to play, with a lot of desire.

“It’s a really good challenge because I’d love to get this football club what they deserve, and that’s League football, but I’m also wary and know how tough this league is to get out of. There’s so many good teams and there’s probably more money in this league than I’ve ever known.

“There’s good players coming out of the League and dropping down to this level, as we know in our team ourselves, but generally, really looking forward to the challenge ahead. We’ll keep chasing that last play-off place until it’s mathematically not feasible, and then we’ll start building for the summer and get a squad together that can hopefully challenge for honours next year.”



Each manager in The Bosses’ Lounge also takes on a unique Q&A…

When did you want to start coaching/managing?

Not until pretty late really, because I was loving playing so much. Just loved playing. I think because I came into the game quite late as well I really appreciated it; I didn’t turn professional at Watford until I was 26, so you just want to play as long as you can do. I think the first time was in the main part of working with Peter Taylor (at Gillingham) and that year when we got promoted and I was player-coach. Even though I was still focusing on playing, I then got the bug of going on courses and watching other managers work. Obviously learning from Peter Taylor as well, I thought ‘this is something I’d like to do once my career is over.’ I was able to do it in a dual role and it was a tough job, but I really enjoyed my time in the Championship as player-manager. I think it was round about that year when I was 34 and I thought ‘yeah, I’d love to carry on in the game.’

Which training sessions do you enjoy leading the most?

Basically possession stuff; I love to see players enjoy the football, but also try and win the ball back. In-and-out-of-possession sessions, with a high tempo; I try to make training a real tempo where they should train as they play. More so the possession sessions, but also crossing, finishing. I just generally like training, in terms of putting sessions on that are high tempo.

Will you ever take part in training?

Yes – I shouldn’t, but I do! I still think that I can play! When there’s an opportunity to join in, perhaps at the end of a session where there’s a small-sided game and there’s an odd number. To be fair, I still go round kicking players, thinking I’m playing still! I do like a little run around with the lads and a bit of fun as well.

Favourite ground (other than your own) that you’ve visited or would like to visit

I’ve got a few but I was fortunate to play at the old Wembley twice. I’d love to be manager of a team that got to Wembley. I think having had the opportunity to go and play there, taking a team there as manager would be phenomenal.

Favourite player to watch (past or present)

I think back in my time, because I was a bit of a Tottenham fan, I’m certainly not the same type of player as Glenn Hoddle, but he would have been someone that I looked upon favourably. I was fortunate enough to play against him when he became Swindon Town player-manager. He would have been one that I actually studied and watched, and really enjoyed watching as well. Some of the things he used to do were phenomenal and it was a bit of an honour to play against him.

And how would you sell the club to him if you were trying to sign him (in his prime)?!

Well I think one thing I would say, we’ve got a group of players where I demand a high tempo, but we’ve got to improve with the football. To sign someone like Glenn Hoddle would be phenomenal for us because we could then play a slightly different way, because everything would go through Glenn Hoddle and he’d get us playing more football than perhaps we do. I’d certainly say he’d be our main focus of going through the thirds of the pitch.

Pre-season tour anywhere in the world

I’d go back to Barbados if I could because that’s where we went pre-season at Gillingham when I was the manager. It was a fantastic trip, an opportunity to have some warm-weather training, and so the chance to go back there would be phenomenal.

Most challenging/frustrating part of your job

I think to coach players at League level and then when you drop down – I dropped down the levels at Dover for a few years – sometimes you’re asking players to do things they can’t do, so you have to adjust your coaching style. I found it a challenge, but it’s a nice challenge to have because you’re trying to make players better.

Funniest player/coach you’ve worked with, or just one of the funniest

I still keep in contact with him, from when I first went into Watford, and he started in non-league as well, a lad called Trevor Putney. He ended up playing for both Norwich and Ipswich, and for Middlesbrough, and he sort of took me under his wing at Watford. He’s probably the funniest man I’ve ever come across in football and still to this day I go and see him; he now lives in Spain. Whenever I talk about funny stories his name always comes top of the list, so without a doubt it’d be Trevor.

Most embarrassing moment as a manager (or player)

I suppose the funny moment as a manager where I’ve not thrown a cup of tea, but I’ve gone over the top a bit, which I don’t do very often, was down at Dover. I lost the plot a bit and I’ve kicked the door and my foot got stuck, basically. I broke the door and my foot got stuck in it, so I would say that was my most embarrassing moment, when you’re having a go at the players and you look round and they’re all laughing at you.

Your routine on a matchday

As a player, I was very quiet and tended to try and focus, and I think if my wife was here now she’d be nodding her head, because you get into a routine where it’s match day, your mind’s on it, and I do that still as a manager. I am a little bit superstitious; if I’ve done something leading up to the game then I try to do the same thing if we’ve won. I just follow the normal routine really, but I’m a different character on match day than I am during the week and I just tend to fully focus on the job in hand.

One singer/band or song you would sneak on to the team playlist

I’m just trying to think…the lads’ music taste nowadays is absolutely horrendous, isn’t it? You never understand what they’re saying. It would probably be something like Frank Sinatra ‘My Way’ – I’d have a bit of that in there. I’m sure it’d be turned off within 30 seconds but I’d put that on.

Advice you remember getting that’s stuck with you

The only advice I would say, and the person I got it from was my dad, my late dad, the one thing he taught me was to never give up. My dad played for the Woolwich Arsenal many, many years ago, so he was in the game, but he’d finished his football career so I was never able to see him play, but he watched a lot of games of me playing for Dartford, Redbridge Forest, and followed my career. When I got released by Charlton at 18 it was always a case of ‘don’t give up, keep going, keep working hard and do that extra bit to try and make it.’ That’s what I did really, I kept on going, and I was pleased he was alive to actually see me play quite a lot of games for Watford in the end. He’d be the one that I took most advice from, because he said ‘don’t give up on your dream,’ and fortunately it came at 26.

If you could have some time with any manager, past or present

I was actually fortunate to meet Bobby Robson quite a few years ago. I had a little bit of time to sit down and speak to him, but that would have been one person I would have loved to sit down with and talk about his life in football.

How have you changed since you first started coaching/managing, or what’s the biggest lesson you’ve learned?

I think your man-management skills are so important; you’ve just got to get a group of players and be honest with them. I was honest as a player and I believe I’m honest as a manager, and I think that’s certainly what I wanted as a player. It’s not an easy job, in terms of managing players, and what I said earlier on about leaving players out, but I’m one of these managers who’ll explain what I do. I’m not someone who’ll just leave someone out, because I don’t think it’s the right thing to do; you need to talk to players. I think I’ve learned and become stronger at that over the years.

Any misconceptions about you as a manager/personality, myths you’d like to dispel, or something you wish people could understand a bit more?

Not really. I think the people who know me know that I’m pretty genuine in terms of the way I am, and I manage the way I used to play. I’m not a person who believes in being anything else but myself. I am myself and I’ll always be myself.

And finally, what’s the best thing about having this life around football? When you wake up and football’s your focus for the day, do you still get that same buzz as you always did?

Yeah, 100 percent. You obviously do a lot of work during the week, working with players is great and there’s nothing better than this job, to be fair, doing something you love each day, but the buzz of the match day is the big thing for me. You just can’t wait for the game to start. It’s a fantastic job, I’ve been fortunate to be in it for some time now, and I’d love to continue in that over the next few years. I’d love to get back in the League as the manager of Eastleigh; it’s a work in progress here but I’d love to make that happen.

Interview/article by @chris_brookes

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