King Kenny: The Man To Complete The Six Year Plan?

Brendan Pitcher
8 min readJul 1, 2021

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In just the second question of his first press conference as Leyton Orient’s new manager, Kenny Jackett gave an answer that seemed to neatly encapsulate the methodical manner in which he operates.

When questioned on his new club’s ambitions for the season ahead, he responded by saying “most importantly first, we’ll have to work out a plan.”

The reply was typical of the 59-year-old’s measured systematic approach to management. It’s a way of working that has ensured Jackett boasts three promotions and an impressive win percentage of 44.7% on his CV.

He isn’t the only one with a plan, however.

Despite some considerable hurdles, Orient have bettered their league finish in each of the four seasons since Nigel Travis and Kent Teague took control of the club, and they remain on course to complete the plan they outlined back in 2017 which they hope will see The O’s return to League One within six years.

Their latest managerial appointment feels like the final piece of the jigsaw. It’s rare that a new manager is met with such universal enthusiasm from a fanbase, but that’s exactly the reaction the Orient faithful reserved for the announcement of Jackett.

His arrival in East London might have been met with fanfare, but, as The News’ Neil Allen explains, his departure from previous club Portsmouth caused similar levels of glee from a certain section of their support.

“Pompey fans are used to winning and the problem is Kenny Jackett will always be judged because he came into this football club to get them into the Championship and that didn’t happen”, says Allen.

“His first year was probably his best, we finished 8th and he stabilised us after coming up from League Two.

“The second season we were leading the league for about two and a half months and then lost in the playoffs.

“The third season got curtailed, and we lost in the playoffs again. And the fourth and final season they were top at Christmas before it all went south.

“He was brought in to win promotion and he didn’t, so in that respect people will deem that a failure and he had to go.”

Allen believes that despite continuing to pick up results, it was Jackett’s style of football that ultimately made his position on the South Coast untenable.

“He played in a direct manner with a big man up front. He likes to get it forward quickly and use his wingers. At Pompey, his wingers were his key players, they were his goal scorers. We had Jamal Lowe, who blossomed under Jackett and went onto bigger things and Ronan Curtis who got 40 goals in 140 games.

“It was a style of football that in the end the fans had grown very tired of watching and it was a case of style over substance for the supporters because we were winning games, but they weren’t enjoying the style anymore.”

His failings at Fratton Park cannot be put down to a lack of effort though, with Allen recalling one instance from last season that demonstrates the former Wales international’s insatiable appetite for the game.

“He’s obsessive about his work, he’s a real football man, completely dedicated and absolutely devoted to his job.

“In February he had to have time off to have a mole removed, which was feared might be cancerous, because of this he was meant to be signed off for two weeks. But he ended up directing a game vs Bristol Rovers via the phone from his hospital bed and within days he was spotted around the place. He just wouldn’t take any time off.”

And Allen also feels that Jackett’s enthusiasm towards the game played a part in his arrival in E10.

“I wasn’t surprised when he went to Orient because he just loves football and he’ll give everything to the job. He’s not in it for ego, he’s not in it for finances and even though it involves a League Two club, I’m sure he just wanted to get back into the game. He won’t think it’s beneath him, he just wants to go out there and be a manager again.”

Regardless of the way it finished at Pompey, Allen maintains that Jackett’s performance deserves further retrospection among many of the club’s supporters.

“History should look back on him kindly because he did a very good job. He got them into the playoffs twice and made two Wembley finals. Looking back, he handled himself with great dignity and respect. He received some terrible abuse at times from the fans but never bit back and was incredibly respectful towards the football club.”

If Allen’s positive appraisal makes you believe that this appointment is something of a coup, well that’s because it is.

Kenny Jackett has developed a reputation that has seen him manage successfully across the second and third tiers of the English game for almost two decades. It’s a reputation that has meant he hasn’t needed to drop down to the fourth tier, until now.

The decision to drop down won’t have been an easy one but Foxpunter’s Mike Holden believes it could be further proof of Jackett’s shrewd outlook on management.

“It says a lot about him that he’s chosen to go down to League Two. He’s surveyed the scene in League One and he’s seen all these big managers coming down.

“He’s a manager that likes to build, that likes to take his time and do things properly and I think he probably sees a lot more long-term potential in taking a club by the scruff of the neck in League Two and building it upwards.”

Building a club upwards from League Two into League One is exactly what Jackett did in his first permanent managerial role at Swansea City.

In what proved to be the beginning of an incredible rise for the Swans, ITV Wales’ Guto Llewelyn feels Jackett’s pragmatic and thoughtful approach was just what the club required at the time.

“We’d only just avoided relegation to non-league the season before he joined. The season when he joined we were under Bryan Flynn and had a fantastic start. We were around the top of the league at Christmas, but we fell away towards the end of the season and Jackett joined in April.

“We were an exciting team under Flynn, but what we needed was a bit more maturity and Jackett perhaps made us a little bit more boring and that was actually what we needed really. He gave us solidity, a lot of fight. We turned into a much nastier team and ended up getting promoted in his first full season.”

Llewelyn also believes that Jackett’s role in the club’s journey from League Two to the Premier League has gone under appreciated by many.

“When we look back now at the Swansea success story, it’s often Kenny Jackett that gets omitted from that story.

“Jackett, from people outside of the club at least, is almost forgotten for his part in our rise, and that’s quite unfair because he did introduce a lot of attributes which made a big difference for us in the long run.

“He made us more disciplined, he improved us defensively and he brought in several players who went onto play for us at a higher level.

“Without him, I think it’s unlikely we would have gone on to do what we did. He put those foundations in place which allowed the likes of Roberto Martinez, Brendan Rodgers and Michael Laudrup to have that success.”

After losing out on penalties in the playoff final in Swansea’s first campaign back in League One, Jackett resigned from his position midway through the following season and, after a brief spell as reserve team manager at Manchester City, took up the job at Millwall seven months later.

Jackett enjoyed six successful years at Millwall, he guided them back to the second tier following a four year absence and established them as as a stable Championship club.

Someone who played a key part in Jackett’s success at The Den was Tamika Mkandawire.

Jackett signed the centre back on a free transfer from Orient in the summer of 2010 with his first course of action being to transition him into a defensive midfielder. The Malawian flourished in his new role as he picked up the player of the season award in his first season at his new club.

11 years on, Mkandawire still reminisces about the mentality and organisation his former manager instilled in that Millwall side.

“The preparation that we used to do at Millwall was meticulous. He used to make sure that we were aware of what the opposition can do but at the same time we knew what we needed to do and how we were going to impose ourselves on the opposition.

“We were never scared to play anybody. It was like ‘they have might this but we’re going to impose ourselves by doing x, y, z’ and you always had that confidence going in, you felt prepared.

“We were also extremely fit. That period was definitely the fittest I’ve ever been throughout my career.”

Mkandawire played for both Jackett and current O’s Director of Football Martin Ling during his career and feels that the two will combine well together in their respective roles.

“I think it’s a good blend of personalities. They may have slightly different styles of football. Lingy as a coach always wanted us to attack and move the ball around. Kenny does that too, but I think he also brings that organisation and discipline to a team that is needed.”

Speaking to the 38-year-old you can be left in no doubt as to the level of esteem in which he still holds his former manager.

“You need certain managers at certain times of your career and Kenny is right up there in terms of the managers I’ve played under. He gave me an opportunity and I will always hold him in a high regard for that. I’ve got a ton of respect for Kenny, not just as a manager but as a man.”

With just eight senior players remaining on the books from last season it feels like the start of a new era in East London. And with perhaps a greater say on transfer dealings than some of his predecessors, the squad churn has allowed Jackett the opportunity to build a team in his own image.

That process has already begun with the likes of Darren Pratley, a combative experienced midfielder that Jackett has worked with previously at Swansea, towering centre half Omar Beckles, energetic full back Connor Wood, pacey livewire Paul Smyth and burly forward Aaron Drinan all joining the club in recent weeks.

Going back to his time at Portsmouth, you would suggest his O’s side may lineup in a rigid 4–2–3–1 formation with players that are incredibly hard working and well drilled in their roles.

In his introductory press conference, Jackett was quick to dispel the negative notions held by some Pompey fans about his style of football, saying “I certainly want to attack. I want to try and score goals. I want to be on the front foot. I want to produce an offensive, high pressing, attacking game.”

Time will tell whether that will be the case. Regardless, this appointment alone can be viewed as the type of statement of intent so rarely seen from The O’s.

E10 expects and all eyes now turn to the new man to see if his plan will come to fruition.

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