The summer of 2007 was the most bizarre transfer period in recent Leicester City memory.

Milan Mandarić had bought the club in February and had an ambitious three-year plan to reach the Premier League. The Yugoslavia-born businessman said delays in the deal meant he had missed out on three transfer targets, with manager Rob Kelly making do with a handful of loan signings.

After sacking Kelly and bringing in Nigel Worthington for a short firefighting stint, Mandarić hired ‘Mad Dog’ Martin Allen on a three-year contract at the end of May. The third Leicester City manager in as many months.

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Ten candidates were interviewed, including Neil Warnock, Bryan Robson, Glenn Hoddle and Paul Ince. Terms were agreed terms with Warnock, but Mandarić later claimed during a Leicester Mercury fans’ Q&A that negative letters from supporters persuaded him to pull the plug.

Allen’s first full day in the job was a hectic one. Iain Hume signed a new three-year contract, while Stephen Hughes, Alan Maybury and Elvis Hammond were transfer listed. Don Mackay was appointed sporting director, joining from Middlesbrough where he was chief European scout.

Defender Paddy McCarthy joined Charlton Athletic for £450,000, while Motherwell signed Stephen Hughes for around £50,000. A handful of others left on free transfers. The cash injection from those exits was crucial to a hectic summer of incomings.

Deals for most of the players who arrived that summer were agreed before Allen and Mackay were appointed. Allen found this out when he first met Mandarić in a central London hotel. Despite looking down the list of players and thinking ‘no, no, no, no, no’, Allen took the contract. It was one he described on the Undr the Cosh Podcast as a ‘life-changer’.

The first two signings of the summer – also unveiled on Allen’s first day – were Birmingham City defender Bruno N’Gotty and Aalborg goalkeeper Jimmy Nielsen. Mandarić scouted and bought N’Gotty, who played for Paris Saint-Germain when Mandarić was the owner of OGC Nice. The 35-year-old centre-back signed a two-year contract worth £15,000 per week. An eyebrow-raising amount of money for a Championship team in 2007. Mandarić had started as he meant to go on.

Nielsen, 29, arrived from Denmark, despite Allen wanting to sign veteran Dean Kiely instead. Nielsen claims in his autobiography that he was earning £12,500 per week at Leicester, which he says helped pay off gambling debts so severe that he once lost $350,000 in a casino during a single night. Back home, he had earned the nickname ‘Casino Jimmy’.

In his book, Nielsen speaks negatively about his time at Leicester. He clashed with coaches and receiving several petty fines, some of which he contested successfully. After being demoted to the reserves in August, he was transfer listed by mid-November and his contract cancelled in January.

Nielsen came to Leicester via agent Barry Silkman, who had become close to Mandarić and went on to shape much of City’s summer business. Silkman had strong relationships with the hierarchy at Millwall in the 1990s, when Nielsen had a brief spell there.

Next through the door was Ricky Sappleton, an 18-year-old striker and Silkman client from QPR who had been on trial with Liverpool and Mackay’s former club Middlesbrough. He was followed by Carl Cort, a 29-year-old striker released by Wolves.

Silkman then brought over a player he hyped privately as one of the most underrated young talents in the world. Dutch midfielder Sergio Hellings was tipped for big things, having come through the academy at Ajax before spending time at Anderlecht. He played for the Netherlands at youth level alongside Nigel de Jong, Wesley Sneijder and Arjen Robben.

Middlesbrough tried to sign Hellings during Mackay’s time on Teesside but baulked at the £500,000 asking price. As with Sappleton, Mackay and Silkman had a shared influence in bringing him to Leicester.

Three free agents with experience of English football then arrived, reassuring Leicester supporters. Charlton’s Radostin Kishishev arrived after Allen took a scouting trip to Bulgaria (where Kishishev was on international duty). Right-back James Chambers then came in and was quickly followed by 19-year-old winger Jonny Hayes, who Allen had worked with at MK Dons.

Next was another of the most famous flops in Leicester City memory – another of Silkman’s Next Big Things. Iranian right-back Hossein Kaebi arrived with plenty of fanfare and hype. So much so, the announcement of his arrival on City’s official website was headlined: City Sign ‘The Prince of Persia’.

There was no doubt Kaebi, aged 21, had talent. As an 18-year-old he was named in World Soccer Magazine’s top 10 most promising players, then two years later impressed at the 2006 World Cup.

Mandarić hired Kaebi a translator: Hamid Taheri, a local man who worked with asylum seekers and refugees. He was a large and friendly man who rarely left Kaebi’s side, leading to the duo being dubbed ‘The Iranian Little and Large of Leicester City’.

Allen has since admitted that, when Kaebi first arrived at the Walkers Stadium at 10pm one evening, he ‘thought he was a jockey’ and questioned the chairman about his height.

Allen said on the Undr the Cosh Podcast : “When I saw the size of him, I said: ‘******* hell. Chairman, can I have a word?’”

“Yeah, yeah, yeah, everything OK?” Mandarić asked Allen.

“He’s a bit ******* small, isn’t he?”

“Yeah, but he plays wing-back.”

“Wing-back? ******* hell.”

“Everything okay though? He’ll be worth a lot of money.”

“Chairman, he’s five-foot-*******-six, you can’t have a right-back playing in the Championship at five-foot-six. That’s a hell of a move.”

“We already have the agreement in place. He’s signing now.”

Loanee Shaun Newton then arrived on a permanent deal and was followed by Birmingham City duo Stephen Clemence (£750,000) and DJ Campbell (£2m). Allen knew Campbell, having plucked him from non-league for £5,000 while at Brentford.

Campbell’s arrival was not plain-sailing, and Allen pushed his luck when failing to get hold of Birmingham manager Steve Bruce. “I replied (when told Bruce was unavailable) in my best Scottish accent that it was Sir Alex Ferguson,” Allen recalled a short while later.

“Steve Bruce came to the phone and said: ‘Good morning, Alex’ and I replied: ‘Good morning, Steve. It’s Martin Allen’.

“He laughed and laughed and laughed, and called me a few names. But I got the answer out of him that I wanted and we got a deal.”

Clemence and Campbell were the last signings Mackay saw through. He and chief scout Lil Fuccillo were made redundant on July 20 ‘as part of an ongoing restructure’, less than two months after Mackay’s arrival.

Nielsen, Hellings and Kaebi were three of no fewer than seven players signed via Barry Silkman that summer. It was later reported by the Daily Mail that Mandarić caused ‘unrest’ within the club by paying Silkman a rumoured £1,000,000 in fees. The agent ‘strenuously denied’ this, saying the amount was £250,000.

Silkman told the Daily Mail: “I did a lot of work for Milan in the summer, some of which was highly complicated involving bringing players in from Iran, Denmark and Holland.

“Leicester’s chief executive, Tim Davies, couldn’t get hold of the right people to make the deals work, but I knew all the agents involved.

“I wish I had been paid a million, but it was nowhere near that figure. You can halve it and then halve it again and every penny was properly authorised.

“Milan wanted new players in a hurry, and he knows I have the right contacts.”

Players, too, were unsettled by the signings. Those already at the club earning £2,000 and £3,000 each week were seeing some players arrive on weekly wages of £15,000 and £18,000.

But just as fascinating to look back on are the players Leicester didn’t sign. As you might imagine, there were plenty, and some names far more ambitious than others.

City were turned down by free agents Markus Heikkinen and Lee Hendrie. They failed with a bid for Troyes striker Marek Saganowski, while offers for Southampton striker Leon Best and MK Dons midfielder Izale McLeod were also knocked back.

There were also talks to sign former Middlesbrough striker Joseph-Desire Job from French club Sedan. His agent? Barry Silkman. In fact, Silkman made a rare public comment about Job’s potential Leicester move, telling Sky Sports his client could be joining a club that “begins with L, ends in R and is owned by the former Portsmouth owner”. That move never materialised.

Other names City were linked with included Geraldo (Pacos de Ferreira), Lewis Gobern (Wolves), Leon Constantine (Port Vale), Matt Jarvis (Gillingham), Svetoslav Todorov (Portsmouth), Richard Cresswell (Leeds), Matt Tubbs (Salisbury City) and former Wigan defender Arjan de Zeeuw.

Despite those failed moves, bigger names were already creeping into the chairman’s head. Free agent Robbie Fowler had just left Liverpool after his second spell at Anfield, and Mandarić was insisting City needed more strikers. Try telling that to Iain Hume, Matty Fryatt, DJ Campbell, Carl Cort and Elvis Hammond.

Mandarić held talks with Fowler’s agent George Scott. Despite ambitious offers from Sydney and Port Vale, it boiled down to a two-horse race between Leicester and Cardiff City. Mandarić was pushing hard for Fowler but the Liverpudlian opted for south Wales.

That was far from the end of Mandarić’s hunt for a striker. One Sunday evening in August, as Allen has recalled, he got a call from City chief executive Tim Davies. “What do you think of Jimmy Floyd Hasselbaink?” Davies asked Allen.

“Yeah, he’s alright. What for?”

“Well, we’re in London at the Churchill, the chairman wants to sign him.”

“What for?”

“He thinks he can do a job.”

“We’ve already got five centre-forwards, so… The last time he played was when? His last game was playing central midfield for Charlton and he got took off at half time. And he’s gonna be playing up front for us?”

“Well, the chairman wants him.”

“If the chairman wants him, he can tell the public that it’s the chairman’s signing, it’s not my signing. And I’m not gonna guarantee that I’m gonna play him. But he won’t get in our team anyway. So there it is.”

“Martin, I think you should sign him.”

“Well, Tim. **** it, I’m not. Down to you.”

The next day, Allen left his hotel room to see Hasselbaink sat with three of his ‘people’ at reception. Allen walked over to Hasselbaink and said: “Jimmy! Nice to see you, mate. You okay?”

“Yeah, yeah, yeah. Good to see you,” Hasselbaink replied.

“See ya later then, see ya later,” Allen said.

Hasselbaink’s agent Humphry Nijman asked Allen: “You all okay with Jimmy signing this morning?”

“You’ll have to sort that out with the chairman,” was the reply. “It’s the chairman’s football club. Whatever.”

When the agent asked Allen if he knew about this, the manager said: “No, not really. But hey ho, you’ve got an agreement with the chairman, get on with it.”

At the training ground the next morning, Davies told Allen: “Jimmy’s signing this morning.”

The reply? “Good luck, but I ain’t fronting it up. He ain’t for me. We’ve got five centre-forwards.”

Mandarić also tried to sign Celtic striker Derek Riordan through his agent Jim McArthur. It was another striker signing that never materialised.

By this point, despite what both men were telling the media, tensions were running high between Allen and Mandarić behind the scenes. Frustrations over the attempts to sign Fowler, Hasselbaink and Riordan were a big factor. The loan arrivals of goalkeeper Márton Fülöp and left-back Clive Clarke from Sunderland were an attempt from Mandarić to smooth things over. The truce did not last long.

Allen was called into Mandarić’s office and dismissed on the morning of August 29. The night before, the City manager and his players had witnessed Clive Clarke suffer a heart attack in the dressing room during half-time of a Carling Cup tie at Nottingham Forest.

The defender was resuscitated with mouth-to-mouth and defibrillator shocks. The match was abandoned and Allen visited Clarke in the Queen’s Medical Centre that night before returning to Leicester at 5am.

He had taken advice that the players should gather at the training ground the next morning to talk through the traumatic incident. Immediately after that meeting at 9am, Allen was summoned to the stadium. Despite being ninth in the league after just three games – and celebrating a 4-1 victory over Watford four days earlier – he was sacked at 10:30am.

Allen’s management style at Leicester was not without its quirks. He wrote regular columns on the club website, including gems such as this:

“(The training ground) is just how I wanted it. The flowers, the colour of them, perfect. The attention to detail – just how I asked it all to be done. There is no longer a restaurant here – there is now an operating theatre, which has white boards, smart boards, a computer system set into it, DVDs and an analysis computer system. It is no longer a lounge, restaurant, reading the paper area. It is exactly as it is – an operating theatre. People raise their eyebrows and said ‘What the hell is that,’ but our planning and preparation for the next game will all come from that room.”

And this:

“The prize for the winning team was a Mars Bar each. I’m sure you’d say ‘Crikey’, how would that motivate and stimulate professional footballers who earn good money and play in front of big crowds.

“But when I showed them the Mars Bars this morning for the winning team, they reacted like little kids.

“You do wonder as the manager whether your ideas and techniques would work but they were jumping for joy.

“But then out of the orange plastic bag I pulled the ‘man of the tournament’ award which was a £3.99 summer barbecue utensil set. They loved it!”

Two days after Allen’s sacking, there was, of course, a signing. Marco Ferreira, a 29-year-old winger, arrived on loan from Benfica. He failed to make a single appearance for the club and returned to Portugal in December.

Cort, Nielsen, Kaebi and Hellings were all transfer listed in the run-up to Christmas, with several other signings going on to face similar fates at the club under the later management of Ian Holloway and Nigel Pearson.

Allen was replaced as manager by Gary Megson, who jumped ship after just 41 days, but it could have been a different story for Leicester City. Megson was in a two-horse race for the job and there was almost a now-familiar face leading City out of the summer.

Current Leicester City manager Brendan Rodgers, who was then a reserve team coach at Chelsea, was interviewed for the job but the Leicester board made a last-minute decision to go for Gary Megson instead.

“I nearly came here 12 years ago when I was 34 and I think now, I wasn’t ready if I’d have gone in at that time,” Rodgers recalled shortly after becoming Leicester manager in 2019.

“I was very lucky that Milan Mandarić chose Gary Megson. Twelve years later I’m enriched by all my experiences, good and bad.

“The story was this: I was working at Chelsea in the reserve team and then I got a call, because I think Martin Allen had been here and at that time, I think they were looking for a young manger to come in and it hadn’t quite worked out.

“I think they thought they were going to go with experience and then, however it happened I don’t know, someone had spoken to Milan in terms of me being worth speaking to.

“When I spoke to him, he seemed to like it. We met in Mayfair for about five hours one night. He then wanted to meet again, so I met him again and I think it gave him a problem.

“So the process went on for a little bit of time, and it was great for me because it allows me to go through the whole process of maybe becoming a manager, and then on a Wednesday I got a call from Tim Davies and he said: ‘We were going to appoint Gary Megson on the Monday, then we decided it was going to be you on the Tuesday, but we’ve decided to go for Gary Megson.’

“I said to him: ‘Why didn’t you do it on the Tuesday?’ But I thanked him, I was disappointed I didn’t get it but that was a great experience for me because it told me: ‘You’re ready to be a manager.’

“I wrote a letter to Milan, thanked him for the experience, wished Leicester good luck and got on with my life at Chelsea and a year later I went to Watford.”

Leicester City would go on to be relegated at the end of the 2007-08 season, falling into League One for the first and only time in the club’s history. Allen’s successor Gary Megson jumped ship after just 41 days, while Ian Holloway inherited a difficult hand and was incapable of keeping City up. The club were the Championship’s highest spenders on agents’ fees that season, despite relegation, splashing out a whopping £1,630,287 to middlemen. The previous year, that figure was just £56,117.

Hindsight is a wonderful thing. For Mandarić and for Leicester City supporters, the message behind these wise words – from Ian Holloway in December 2007 – came 10 months too late: “What I have got to do is to stop all these agents ringing my chairman, telling him they have got the best player under the sun.

“Other people have been abusing Milan’s enthusiasm because he wants it so badly. Sometimes when you want something so badly, all you do by chasing it is push it further away.”

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