Unsung, underrated and yet a crucial component of Everton’s rise under David Moyes, Leon Osman was the last of the 1998 FA Youth Cup winning team to break into the Everton first team. 

Richard Dunne, Tony Hibbert, Francis Jeffers and Danny Cadamarteri had all stepped up by the time Osman’s chance belatedly came in 2004 (with Jamie Milligan and Phil Jevons earning cameos too), but the wait was certainly worth it. Indeed his contribution to the Everton cause outshone those whose chance came earlier, and he ended his career tenth in the list of all time Everton appearance holders.

Born in Billinge to an English mother and Turkish-Cypriot father, Osman rose through the Everton academy and represented England schoolboys. He shone in the first leg of the FA Youth Cup Final victory, scoring a spectacular third goal, but then suffered a serious injury which brought question marks over his entire career. 

‘It was a long way back but I never thought I was finished,’ he told the Daily Mail in April 2012.  ‘It just felt that it was another hurdle I had to get over. It dragged on for three years in total but it never came to the point where I thought to myself: “I'm struggling to make it here.”’

During this wilderness period most of his youth cup winning teammates moved on, some earning international recognition too.  Osman was loaned out to Carlisle United in the 2002/03 season and then to Derby County a year later.  His first team breakthrough with Everton came at the end of the disappointing 2003/04 season, as his 23^rd birthday neared. He never looked back.

Diminutive, composed, versatile and technically excellent, Osman blossomed in his first full first team season – 2004/05 – which concluded with Everton qualifying for the Champions League. Perhaps lacking some of the pace that might have elevated him to regular international football, he was an important part of Everton’s developing short passing game. His willingness to fill positions on the right, in central midfield and occasionally operating behind a forward were integral to Everton’s progress. Purportedly more glamorous players – like Simon Davies, Manuel Fernandes and Royston Drenthe – came and went, but Osman was always someone that David Moyes could rely upon.

His best form came in late 2007 when he was given a run in his favoured central midfield role. It was no coincidence that with Osman as the fulcrum that Everton embarked on a lengthy unbeaten run, playing some sumptuous football. Osman also scored some glorious goals during this period, few better than a 22 yard effort against AS Larissa in the UEFA Cup: A brilliant counter attack started by Tim Cahill, an overlapping run from Leighton Baines, a flick from Steven Pienaar and a swerving finish from Leon Osman. A 30-yard dribble past three opponents and dinked finish against Sunderland a month later ran this effort a close second.

There were occasionally question marks posed over a lack of pace and ability to dominate games. Sometimes he seemed a victim of his own versatility; pushed out of one position to accommodate another player. But those who watched him week in week out were appreciative of his true value to the Everton team. ‘He is a player who has often divided opinion at L4, with some questioning his lightweight frame,’ recorded the Everton tactics blog, Executioner’s Bong. ‘For me, Ossie is a top player; he has two quick feet, possesses vision, great touch, can score goals and always puts in a shift. In a national game like ours obsessed with physicality and pace, Osman is something of an oddity.’

Osman appeared in the 2009 FA Cup Final and his return to fitness in the second half of the 2011/12 season coincided with Everton’s return to Wembley for an FA Cup final with Liverpool. A fortnight after that disappointment he made his three hundredth Everton appearance.

‘Ossie’s been a terrific player for the club over the years and he’s continued to grow over the years. He’s a massively important player for us now,’ said Leighton Baines after that landmark was passed in a 4-0 home romp against Fulham. ‘Since I’ve been here, I think he’s got better every year really and become more and more important to us. I thought last season he was great and this year he’s been fantastic again. He’s a vital part of the squad and the team.’

Having represented England at youth level in the 1997/98 season, 15 years later, at the age of 31, Osman was called up for full international honours, appearing in a friendly defeat to Sweden in November 2012. The following spring he appeared in a World Cup qualifier against San Marino.

‘I think it has probably taken Evertonians a long time to appreciate how good he is but there has never been any doubting his ability,’ reflected Joe Royle in 2012.  ‘With smaller players you wonder whether they are strong enough to play in the middle [but] as he has developed and grown stronger and got more football knowledge he can play there comfortably now.’

After Moyes’ departure as Everton manager at the end of the 2012/13 season, Osman continued to be a mainstay of the Everton midfield. He appeared in every Premier League game in the 2013/14 campaign as the club narrowly missed out on Champions League qualification. At the end of that campaign he was awarded a testimonial, against Porto.

Speaking to the Independent newspaper around that time of the slow-burn start to his career, he said that growing up with one leg several centimetres longer than the other had contributed to his early injuries. He admitted to being ‘jealous’ of the teammates who had made the breakthrough ahead of him, ‘but looking back now I wouldn’t swap the way things went.’

‘Maybe making me wait for it made me hungrier. Having come up against a brick wall a couple of times maybe some players would have lost hope and given up, but if I come up against a brick wall I try to find a way around it.’

He added that his career was helped too, by the Premier League’s evolution in the noughties from being a rough and tumble game, to one where skill and technique were more highly valued.  “[In the] early 2000s it was a very physical game and then Spain went and showed that small, technical players can win you World Cups. Only after that did people maybe see me and what I can bring to the team.”

In November 2014 he extended his contract to the end of the 2015/16 season. He celebrated by scoring the winner in his next match, his four hundredth for Everton, against West Ham United. Playing as an auxiliary holding midfielder, as Everton broke Osman ran the length of the pitch before sliding home Samuel Eto’o’s intelligent cross.

‘He was marshalling the back four and dictating the play so the last player you expect on a counterattack was Leon Osman,’ said his manager, Roberto Martínez. ‘He is a great ambassador for our football club. He was outstanding throughout the game.’

This, however, would be his last league goal at Goodison. A foot injury sustained soon after kept him out for three months, and thereafter he found himself an increasingly peripheral player as Martinez’s Everton player faltered. His final appearance came in a dismal 3-0 defeat at Sunderland in May 2016 – Martinez’s last match as Everton boss.

Martinez had promised Osman another year at the club, but when Ronald Koeman succeeded the Spaniard as manager, Osman’s two-decade long association with the Blues came to an end.

'When the new manager came in, I didn’t presume he would honour the promise given by the previous manager,' he told the Sunday Times in January 2017. 'I had been in the game a long time. If I wasn’t part of his plans, well that was perfectly fine. My wife will tell you I am not one to hold grudges. I am unable to do it.

'One sleep, then I will wake up and start over again. And you know, that happened. I was disappointed but then you move on. I am still an Everton supporter, I am able to coach with the youth team and I still go to games as a fan.'

Retirement brought a new career for Osman, as a thoughtful and eloquent TV pundit and analyst.

A true one-club man, Osman epitomised loyalty, consistency and professionalism throughout his career. With his deft touch, intelligence on the ball and an eye for goal, he became a central – if not underrated – figure in the Toffees’ midfield over his long tenure at Goodison Park. Only nine other players have worn the royal blue of the club more times than Osman and his 433 appearances rank him alongside Dixie Dean. He was, wrote the Observer’s chief football writer, Paul Wilson, Osman, ‘Everyone's favourite unsung hero, one-club player and local boy made good.’