Football League World
·26 January 2025
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·26 January 2025
Striker Jay Simpson deserved the Orient send-off he received in 2019.
Jay Simpson will always be remembered for his efforts in East London throughout his career. The striker had two spells with Leyton Orient - his first spanning from 2014-17, while his second only lasted a few months.
Although it wasn't exactly memorable for the now-36-year-old, his second spell with the O's was a perfect goodbye to professional football in England.
Simpson started his career as a promising prospect at Arsenal, becoming the first ever player to score a hat-trick at the then-new Emirates stadium in a Youth Cup tie against Cardiff City in February 2007.
He went on to spend the 2007/08 season on loan at Millwall, during which Arsenal manager Arsène Wenger was quoted as saying: "He has done extremely well and has scored goals. I always thought Jay was a very good player and the fact he can get good experience at Millwall makes us all happy, because he is not only a good player but a very nice boy."
A pair of loan spells at West Brom and Queens Park Rangers followed before the striker went on to make a permanent move to Hull City. Simpson spent three seasons with the Tigers, making 86 appearances and helping them achieve promotion to the Premier League - a reward that he was unable to reap as he was released the following summer.
In September 2013, he joined Thai Premier League champions Buriram United, where he won the Kor Royal Cup, scoring the winner in a 1-0 win. However, he terminated his contract after only a few months and eventually signed a three-year deal with the O's in July 2014.
Prior to Simpson signing with the club, Orient had just been defeated on penalties in the League One play-off final. The club had been sold to Italian businessman Francesco Becchetti and only a few months later manager Russell Slade departed to join Premier League side Cardiff City.
His first year with the O's was troubled by many factors out of his control, being sidelined between November and February with injuries, as well as the club going through four managers in a single season. The striker could only manage eight goals in 34 appearances as Orient were relegated to the fourth tier for the first time since 2006.
His second year was a lot more prolific for Simpson, scoring 25 goals in all competitions and being named in League Two's Team of the Year. However, the O's couldn't bounce back and could only muster an eighth place finish - which inevitably led to links of Simpson departing the club.
At the start of the 2015/16 season, Simpson missed the opening game of the season, with the club citing an illness as the reason why. However, Southend United manager Phil Brown confirmed the club were in talks to sign the striker. A move failed to materialise, but Simpson struggled for form - only scoring his first goal of the season in mid-November.
By the end of December, Simpson's future was made a lot clearer, with manager Andy Hessenthaler stating: "Jay has asked to leave the club and on the strength of that, I thought it best that we didn't involve him today, but that's all I'm going to say on that one."
Eventually, MLS side Philadelphia Union signed Simpson, where he went on to score four times in 34 appearances before being released at the end of the 2018 MLS season. Simpson remained without a club until February 2019, when it was announced he had returned to East London.
At the time of his arrival, Orient were leading a strong promotion charge in the National League, as well as looking to book a trip to Wembley for the first time in five years via the FA Trophy.
Depth was needed in East London, and Simpson's arrival was well appreciated, with him starting a home fixture against Maidenhead United just four days after being announced by the club.
Although the goals weren't as free-flowing during his second spell as they were during his first, he still provided the O's with a valuable moment - scoring his solitary goal of his return during a 3-2 win away at Barrow.
He was eventually dropped for the final five games of the season, with Justin Edinburgh opting for the ever reliable pair of Macauley Bonne and Josh Koroma as the O's went on to secure the National League title.
Although Simpson maybe didn't put up the numbers he would have wanted to, his impact was just as crucial as any other player in the squad. He departed the club for the second time the following summer, leaving with a league winners medal and enhancing his legacy in East London.
The striker went on to spend a year with Cypriot club Nea Salamina and had an ill-fated spell with non-league side Welling United, but for most fans his legacy will always remain etched into Orient history.