When striker Chris Dagnall stepped up to the penalty spot in Wembley on 25 May 2014, nobody could anticipate what would follow for Leyton Orient. It was the 2014 League One playoff final, Orient were playing against Rotherham, and the game was to be decided by a penalty shootout.
The Os took the lead in normal time, with Moses Odubajo putting them 1-0 up in the 34th minute before Dean Cox doubled the London side’s lead just five minutes later. However, a second-half brace from Rotherham forward Alex Revell meant the match would go to extra-time and penalties.
Orient took the lead in the shootout, Lee Frecklington missing Rotherham’s second penalty as Orient converted their first three. However, after centre-back Mathieu Baudry’s miss, the score was level, and Dagnall’s miss gave Richard Smallwood the chance to win promotion for the Millers. He did exactly that.
Orient were left heartbroken. The club finished above Rotherham in the league, both sides earning 86 points, though Orient had a better goal difference. However, coming third wasn’t enough to send the team up to England’s second tier and it represented the start of Leyton Orient’s downward spiral.
On 7 July 2014, just a month-and-a-half after Orient’s heart-breaking playoff final defeat, the catalyst for their true descent took place. Long-time owner Barry Hearn sold his 90% percent share in the club to Italian businessman Francesco Becchetti. Becchetti’s business was in renewable energy and waste management and, before taking over Orient, the Italian was touted as a potential suitor of Bari and Reading. Hearn would later, in an interview with The Telegraph in 2017, describe selling the club to Becchetti as “an absolute disaster.”
In the same interview, Hearn, who is an Os fan and sports promoter, justified his decision to sell as a result of pressure from the fans: “Three years ago, I was so optimistic about the future of Leyton Orient it’s not true. Because I saw a man with enthusiasm and passion, who was moving to London, had loads of money, gave the fans what they were always asking me for: ‘When are you going to get your chequebook out?’ Well, he got his chequebook out and this is what’s happened.”
Hearn’s selling of Leyton Orient was, at the time, completely justified and he should not be blamed for what would happen next. The Matchroom Sports chairman had owned Orient for 19 years, taking over in 1995 – but now the Hearn era was over and the Becchetti nightmare was about to begin.
Becchetti delivered on his immediate promise and pumped money into the club. Orient signed Gary Woods, Adam Legzdins and Bradley Pritchard on free transfers, as well as Jay Simpson and Jobi McAnuff, who would become fan favourites and who are both currently at the club, serving second stints after spells away.
These big-wage signings showed promise as Orient set their sights on another promotion-contending campaign. After an opening day home loss to newly-promoted Chesterfield, Orient managed a meagre two wins and four draws from their first eight games. By 24 September, manager Russell Slade, who had been at the club since 2010, resigned from his role, days after Orient rejected an approach from Championship side Cardiff. Slade would later go on to replace Ole Gunnar Solskjær in Wales after the Bluebirds were relegated from the Premier League.
Under Slade’s management, Orient had qualified for the third round of the League Cup, defeating Plymouth on penalties in the first round and beating Aston Villa away. Slade would manage the team for the third round, which was a home tie against Sheffield United that saw the Os lose 1-0 thanks to a second-minute goal from Michael Higdon for the Blades. Slade also helped Orient defeat Peterborough in the first round of the Johnstone’s Paint Trophy, Chris Dagnall scoring a brace in a 3-2 win.
Caretaker manager Kevin Nugent would replace Slade at Orient, winning just once, drawing twice and losing three in his third stint as manager of the club. On 26 October, Nugent was replaced by sporting director and former Napoli, Inter and QPR defender Mauro Milanese, who had come to Orient during Becchetti’s takeover.
Milanese’s spell in charge would last just six weeks, the Italian sacked on 8 December after winning just one league game in his time and seeing the club crash out of the FA Cup at Oldham. Despite this, Milanese secured a 2-0 win against Dagenham & Redbridge to put the team into the southern quarter-final of the Johnstone’s Paint Trophy, which the Os won 2-0 against Northampton.
Milanese’s final game would be the southern semi-final against Gillingham at Priestfield. Orient fought hard but fell to a 79th-minute winner from Josh Egan, knocking them out and pushing the Italian out of the hot seat shortly after.
Milanese returned to his position as sporting director and former Lazio and Fiorentina player Fabio Liverani was appointed as manager. Liverani’s last spell before Orient was an ill-fated and brief stint at Serie A side Genoa, fired just seven games into the 2013/14 season with just one win to his name.
Despite losing his first two games, Liverani won the last two games of 2014 convincingly, beating Crawley 4-1 and Yeovil 3-0 just three days apart. However, the damage had already been done and, in 23 league games in 2015, Liverani won just six and Orient were relegated from League One, finishing in 23rd, just three points from safety. Liverani left the club in May, replaced by former club defender Ian Hendon, who had most recently served as a coach for Sam Allardyce at West Ham.
Orient had to let go of various stars following their relegation to League Two. Romain Vincelot, their 2014/15 top scorer, Chris Dagnall and Adam Legzdins, amongst others, all departed.
Hendon enjoyed an optimistic start to the club, winning his first five League Two fixtures to put Orient top of the table. They did, in this time, crashing out in the first rounds of the League Cup and the Johnstone’s Paint Trophy, however. After his positive start, things quickly began to spiral for both Orient and Hendon. Over the next 20 games in League Two, Orient would win just four times; leading to Hendon’s eventual dismissal in January.
This period is most notably remembered for what happened after Orient lost 3-1 to Hartlepool on 15 November, after just two wins in their previous 12 matches. Becchetti demanded that the team and six staff members stay in the Marriott Hotel in Waltham Abbey, just five minutes away from the club’s training ground, for a week in an attempt to “help team bonding.”
Orient defeated York in their first match after this bizarre move by the club owner, before one win in their next eight led to Hendon’s sacking. His assistant, Andy Hessenthaler, took over as caretaker manager for three days before Kevin Nolan was signed as player-manager.
Nolan had just completed a four-year spell with West Ham, leaving by mutual consent after 141 league games for the Hammers, including three full seasons in the Premier League. Despite being 34, he could still serve as an important option in Orient’s midfield, as well as providing a fresh managerial take for the struggling side.
Nolan won five of his first seven league games in charge as Orient looked back in contention for a promotion push, but five wins from their last 13 games left the Os six points off of seventh-placed AFC Wimbledon, who occupied the final playoff spot and would, eventually, be promoted to League One.
Nolan gave up his managerial duties to Hessenthaler in April, with the club close to the playoffs with five games remaining, yet the former Bolton player remained in a playing capacity until the summer.
The summer of 2016 was truly the beginning of the end for Leyton Orient’s 112-year spell in the Football League. A flurry of departures ensued with fan favourite Dean Cox having his contract unfairly terminated by mutual consent and eventually leaving after the transfer window shut to join Crawley in January on a free. Another player mistreated by the Italian owner was Scott Kashket, who moved to Wycombe, where he still plays today. Jobi McAnuff, Sam Ling, Mathieu Baudry, Kevin Nolan and Connor Essam all departed East London as the Os made a handful of signings to replace them.
Left-back Josh Doherty, Yvan Erichot, Liam Kelly and Teddy Mézague were the notable signings in the summer before the 2016/17 season, but Orient struggled to truly replace the stars that had left. The club had a mixed start to the season, winning two of their first five in the league and narrowly losing to Fulham in the first round of the League Cup. However, just one win in four games in September led to Hessenthaler being sacked.
What ensued next was chaos: five different managers between 26 September and 30 March; 29 league matches played; six wins, three draws and 20 defeats. Star striker Jay Simpson left for an undisclosed fee to join Major League Soccer outfit Philadelphia Union, left-back Josh Doherty was released after just six months at the club, and Žan Benedičič, who signed in September on a free, joined Italian side Olbia.
Omer Riza took over at the end of March for the rest of the season, overseeing just one win in the last seven games and finishing rock bottom of League Two with 36 points. Orient would no longer be in the Football League – for the first time in 112 years.
In April, the club’s erratic owner Francesco Becchetti dominated headlines once again as it was revealed that he had not paid staff and player wages for two months, causing the PFA to step in and loan players half their wages. Becchetti had destroyed Orient and didn’t even have the guts to stand before the fans and admit it.
Animosity was at an all-time high and relegation to the National League was a bleak prospect for all. Becchetti faced financial difficulties at the club, too. In March it was announced at a winding-up hearing at the High Court that Becchetti had until June to either sell the club or pay off the debt. On 22 June 2017, Orient’s cloud of relegation had its silver lining: Becchetti had sold the club to lifelong fan and Dunkin’ Donuts brand CEO Nigel Travis. Dallas businessman Kent Tague was a principal investor in Travis’ takeover and would serve on the board of directors.
The following National League season wasn’t filled with as much success as was hoped but provided a vital learning experience and prepared the revamped Orient side for their climb back up the Football League. Steve Davis took over as head coach in July but was sacked by November after a poor run of results.
Justin Edinburgh, who remains as manager to this day, joined the club at the end of November and, under the new boss, the team finished in a mid-table but underwhelming 13th place. It wasn’t the immediate bounceback that many had hoped for but, after what the fans had endured with Becchetti, it was at least a welcome break from the off-pitch chaos.
The 2018/19 season has been a much better affair for Leyton Orient so far, with the Os looking towards promotion. The future is finally bright again for a club that has endured the darkest period in its proud history but, crucially, has lived to tell the tale – a familiar one in England of shady investment, trigger-happy owners, and a gutting from the inside out.
By Sam Wilson @snhw_
Photo: Leyton Orient FC/Jonny Davies