Leon Osman Exclusive On His Everton Years And Burgeoning Media Career

In an in-depth interview that appeared in Everton’s matchday programme for Saturday's Merseyside derby at Goodison Park, Leon Osman speaks about a media career catching fire more quickly than his slow-burning start in football – and 25 years with the Blues which were a triumph for the midfielder’s perseverance and resilience.

Leon Osman laughs and reclines in his seat, spreading his arms to feign indifference, to illustrate the tale of his debut as a Match of the Day pundit.

“Ooh,” gasps Osman. “That was nerve-wracking, it really was.

“I wanted to appear as relaxed as possible, so I sat right back in my chair.

“It was Match of the Day 2. I was on with Mark Chapman and Jermaine Jenas and they were sat bolt upright.

“I look like I’m on my couch next to them.

“Someone told me after, ‘Leon, you can’t sit like that’.

“I learned very quickly.”

Osman is an increasingly prominent media figure, bridging television and radio and excelling on both platforms with his sharp mind and humour and structured and insightful delivery.

He is unsure of his destination but since starting as an Everton talking head soon after retirement four years ago Osman has travelled a long way.

“I am always stretching myself and pushing further,” he says.

“I want to do what I am doing better than I am doing it now.

“I have learned a lot but there is much more to learn.

“I am moving towards somewhere; I don’t know where.

“But nothing is comfortable.”

Osman’s accelerated progress in his second profession represents the polar opposite of the protracted beginning to a football career he finished level with Dixie Dean on 433 Everton appearances.

“But Dixie scored more in one season than I did in my career,” notes Osman, his trademark self-depreciation doing an injustice to a record of 58 Everton goals.

Osman’s modesty masks the insatiable appetite for improvement and deep-seated drive he summoned when interminable injuries, rotten luck and external doubters were seemingly conspiring against the midfielder’s attempt to follow a cohort of his fellow Everton 1998 FA Youth Cup winners into the senior ranks.

In his pursuit of personal growth he is “always watching everybody around me to see how they do things” – and to explain that point, Osman recalls noticing Tony Hibbert’s clean striking of a football.

“At 19 or 20 I asked Hibbo to coach me to ping a ball,” says Osman, painting an unlikely picture.

“He was great at it. I wasn’t.”


The youth-team colleagues would retreat to the Little Wembley pitch at Everton’s old Bellefield headquarters after training; hard-as-nails, doughty full-back Hibbert imparting technical advice to the nimble, ball-playing Osman.

It was soon after these extra-curricular sessions, which lasted “a few months”, Osman reached his injury nadir.

The catalogue of setbacks which started in May 1998 with Osman plummeting from “the top of the world to a state of devastation”, began drawing to a close three years later as the player vomited into a bucket next to his hospital bed.

Osman sustained a blow to his knee 10 minutes after whipping a dipping volley over Blackburn Rovers goalkeeper Gareth Stewart at Ewood Park to complete Everton’s 3-1 first-leg youth cup final victory.

Pictures recording Everton players celebrating after the second-leg 2-2 draw seven days later exclude Osman, using crutches to remain upright on the periphery.

“To go on the pitch and celebrate didn’t feel natural and being young and naïve I missed out,” he says.

“It was a tough start to a pretty hard three seasons.”

Osman would, reportedly, have six operations in that timeframe but “I decided to not keep count”.

The original injury stubbornly refused to clear, then it was discovered one of Osman’s legs is “considerably longer than the other”.

He had ankle ligament and back trouble after his boots were fitted with a platform to “straighten my back and take pressure off my knee”.

After correcting those issues another knee problem required surgery.

Osman clearly recalls the chain of events after coming round from that operation.

“The surgeon had tidied up the cartilage which kept going,” starts Osman, “but he’d found the ultimate reason I was consistently doing it.

“He told me, ‘You have no ACL [anterior cruciate ligament), it is hanging by a thread.

“You will spend four-to-six weeks getting over this operation, then I will bring you back for the ACL repair and you will be out for about a year’.

“I got a big, hot flush to my head.

“He went out the room and I immediately vomited into a bucket by the side of the bed.

“I was in shock.

“But I gathered my thoughts and started redefining my aims, right there in bed.

“People had told me, ‘You’re not going to have a career, you can’t stay fit, you won’t play past 21’.

“But I finally knew the problem.

“My back and ankle were sorted.

“We were going to get my knee sorted, then it would be all systems go.”


Osman had the ACL surgery in July 2001 and doesn’t know what he’d have done had his football career run aground. “Probably gone to college,” is all he can muster.

The game consumed him and he excelled at it.

Osman joined Everton aged 10 following one year with Oldham Athletic and self-schooled in applying his low, slim frame to significant effect after playing two years above himself for Sunday League team Elmers Green.

“I had to find a way from the beginning,” says Osman.

“I learned how to keep the ball really close to me.

“If I went shoulder-to-shoulder with someone I needed every ounce of strength in my body to not fall over.”

In tandem with his parents, who instilled in their son “the importance of manners and the drive to achieve something”, Everton’s Academy shaped Osman’s character.

Unusually, he cites his peers as influences: Hibbert, Michael Ball, Danny Cadamarteri, Richard Dunne, Phil Jevons, Jamie Milligan and Adam Farley – all First Team debutants before Osman – “demanded you play well”.

“You are with them so much that they dictate a lot of your personality,” continues Osman.

“Their desires and needs and manners, even their accents, everything rubs off.

“You had to play your best football in every game and every training session.

“We kicked lumps out of each other.

“But there were always handshakes coming off – well, most of the time.”

Osman’s steepest learning curve “technically and physically”, he discloses, came between the ages of 16 and 19.

“We’d be playing Manchester United one week and Marine the next,” says Osman of a diet of games against rival academy teams that would test skill and mental agility and the Lancashire League football which examined the capacity to “battle” and stand your ground.

Coach John McMahon would join training matches and “not go easy on you”, while youth team manager Colin Harvey was uncompromising.

“Colin’s standards were set as an Everton teen and he wouldn’t allow you to lower yours for a second,” says Osman.

“You never wanted to be the one who cost that group of lads and coach.

“I loved it.

“I wanted to win and be the best player, the player who set up or scored the winning goal, in every session.”

Manager Walter Smith didn’t share Osman’s conviction he “just needed a chance” during a rare extended period of fitness after the turn of the century.

A glut of First-Team injuries nevertheless opened a space on the bench for Osman for a 2-0 win over Arsenal in November 2000.

Barring calamity, he was a shoo-in for the squad against Chelsea the following Saturday.

Cue calamity.

“We were jogging round Bellefield and stopped for stretches,” starts Osman.

“Peter Clarke went to stretch his thigh, just as I bent down to stretch my hamstring… and he booted me in the eye.

“Within 30 seconds I looked like Rocky.

“There was blood everywhere, you couldn’t see my eye.

“I needed six stiches in my lower eyelid.”

Osman’s bid to win over Smith’s successor, David Moyes, was an elongated process, taking in moves north and south and a deal of frank conversations.

Loan spells with Carlisle United in League Two – Moyes’ assistant Alan Irvine championed Osman’s talent and “pushed” for him to gain playing experience elsewhere – and Championship Derby County bookended a sprinkling of games from the bench for Everton.


In November 2003 Osman came on for the closing 12 minutes of a League Cup tie at Middlesbrough.

His weak effort in the ensuing penalty shootout was saved by Mark Schwarzer and Everton lost 5-4.

“I thought taking one was a way of showing I could play at that level,” explains Osman.

“I was the only one who missed and found that tough to deal with.

“I am glad I had the guts to put my hand up but I probably shouldn’t have been allowed.

“I was nervous. I knew how much was riding on it for the Club and myself and maybe that got the better of me.

“My thought before both loans was, ‘If I expect to come back to Everton… I had better be the best player in those teams.

“I loved both spells. They added to my ability and told me I was ready to play Premier League football.

“My time at Derby convinced David I was ready.”

Osman had been back from the East Midlands one week when he scored two minutes into his first Everton start, at Wolverhampton Wanderers in May 2004.

Everton lost 2-1, their season petering out and climaxing in a “shocking” 5-1 defeat at Manchester City, which prompted Moyes, in Osman’s words, “to go absolutely berserk”.

The manager would oversee a startling turnaround, an Everton team with “fight in our eyes” and “galvanised” by an uplifting Stateside pre-season finishing fourth the following season.

Osman’s mix of guile, imagination and industry was a snug fit on the right of a five-man midfield. His six goals – including last-ditch winners against Southampton and Portsmouth – were worth nine points: the difference between fourth and 10th.

When Everton played Champions League qualifying matches against Villarreal in August 2005, however, Osman was replaced in the team by new signing Simon Davies.

“I was very frustrated but it was another challenge,” says Osman.

“I’d have to play well, maybe kick him [Davies] a bit in training.

“Across football, it may be easier to leave out academy players because they don’t complain.

“But it taught me you should ask questions.

“Not being disrespectful or demanding but ask for an explanation.

“I did that and, I think, in David Moyes’ eyes’ changed from a youngster into an experienced player.”


Osman maintains Everton “felt we were going to win every game” at the height of Moyes’ 11-year reign.

In seven seasons from 2006/07 Everton’s finishes read: 6, 5, 5, 8, 7, 7, 6.

Osman attributes Everton’s lack of something tangible to show from that period to a relatively shallow squad depth.

He heaves a plaintive sigh at the memory of coming tantalisingly close in the 2009 FA Cup, a “ridiculous” Chelsea team beating Everton 2-1 in a final when Osman was reduced by his “hardest opponent” Ashley Cole to “basically playing on the right of a back five”.

“I was better in the centre where my pace wasn’t exposed,” adds Osman. “That was a tough day and tough to take.”

Everton defeated Liverpool 1-0 en route to the final but Osman counts a different single-goal victory as his favourite all-Merseyside game.

“Everyone was saying Liverpool would stop our run,” he says of the first of his 21 derbies in December 2004, settled by Lee Carsley’s strike, “ that the wheels would fall off… but we beat them and I was involved in the goal.”

For Osman, any defeat felt like a personal affront.

“Oh, yeah, jeez,” he says, his one concession an international debut when Osman “came off the pitch really pleased” despite England losing 4-2 in Sweden in November 2012.

“But I was murder to be around for a few days if Everton lost,” continues Osman.

“I still am.”

It was a paucity of action grating Osman in his final season.

Discussions with Roberto Martinez over the issue, he insists, following a booming laugh, “will stay between us”.

Osman’s first season under the Spaniard after Moyes left in summer 2013 was an unqualified success, featuring in every Premier League game as a freewheeling Everton finished fifth.

But his playing-time diminished and Tim Howard wrested Everton’s Premier League appearance record from Osman.

“Roberto took the handbrake off and initially it was great,” says Osman.

“But he didn’t think I could help improve results in the following two seasons, which was very frustrating.

“Ultimately, though, the manager makes his decision and you respect it.

“The hardest part,” laughs Osman, “was watching Tim pass my appearance total (Howard played 354 top-flight games to Osman’s 352) while I sat and watched every one of them.

“On the whole, no, I don’t miss playing.

“I would be an outcast today, these are players from a different generation.

“I played in three different Everton sides but I wasn’t really part of that team at the end.

“Was I ready to retire?

“My whole body, no. My mind, no.

“My knee, probably.

“Once I’d stopped – I was planning on… no, I’ll stop there.”

Thrice-weekly fitness sessions, over two years, with a handful of ex-teammates and boxer Tony Bellew, overseen by former Everton Head of Sports Science Dave Billows, provided an invaluable haven where Osman could “wind down from the routine I was in for 20 years”.

He initially edged into coaching but “couldn’t see where I was going” in that sphere.

“Then media came along,” he explains, “and suddenly I was getting work chucked at me.”

Osman concedes he “found it difficult to criticise anyone” at the outset.

“And if I was with experienced pundits, I thought, ‘They will know more than me’.

“But I have become more comfortable being myself and giving my opinion.”

The best advice he’s received in his new occupation?

“Be honest and be yourself.”

Two qualities which come very naturally to Leon Osman.