As Arsenal have faced a largely barren two-decade spell which saw them fall short in the elite major honours, certain members of the playing staff throughout this period opted to depart for a new challenge. However, as the saying goes, the grass isn't always greener, as this group of former players found out.
That wait for England's greatest domestic accolade could be ended in two months' time, as Mikel Arteta's outfit sit eight points clear of Manchester City with 10 games to play. Had things turned out differently, a number of players who opted to ply their trade away from north London could have been part of this incredible journey.
Whether it was the player or the manager's choice, a feeling of regret can often overwhelm the departed individual. Here, football.london takes a look at seven recent Arsenal players who struggled to reach the heights following their departure from the Emirates Stadium.
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Alexis Sanchez
If ever there was an example of the grass not always being greener, then Alexis Sanchez is chief among the contenders. Between 2014 and 2018, the Chilean scored 80 goals across 166 appearances and was one of the Premier League's most feared attackers under Arsene Wenger.
Having showcased his magic at the Emirates Stadium, the manner of Sanchez's exit, and his performances prior to leaving the club, led to his once-cult hero relationship with the fans turning sour. After an agreement with Manchester City fell through, he agreed a move to rivals Manchester United instead, with Henrikh Mkhitaryan moving in the opposite direction.
Signs of what was to come from his disastrous spell at Old Trafford were there from the very beginning, as he later revealed. "Sometimes there are things that you don't realise until you get there and I remember the first training session I had, I realised a lot of things," the now-34-year-old admitted.
"After the session I got home and I told my family and my agent: 'Can you not rip up the contract to go back to Arsenal?' They laughed, I told them there's something that doesn't sit right, it doesn't seem good. But I already signed, I was already there. After the first few months I carried on having the same feeling, we weren't united as a team in that moment."
Aaron Ramsey
Aaron Ramsey was one of the longest-serving Arsenal players during Arsene Wenger's latter days as manager. Having been signed in 2008, the Welshman spent the best part of a decade at the Emirates Stadium, playing a crucial role in FA Cup triumphs and regular Champions League qualification.
However, time was called on his Gunners career in 2019 when he decided to pursue a venture with Juventus after signing on a free transfer. The north Londoners found themselves in a difficult position after they allowed Ramsey to enter the final year of his contract, and an agreement couldn't be reached between the two parties, despite his obvious love for the club.
He later explained what he believes to be the truth behind his departure from Arsenal. "It all happened... I agreed to a contract they proposed," he revealed last September. "Things went quiet for a few weeks. I was telling my agent, 'Let’s do it', then all of a sudden the contract was no longer there. So there was nothing to sign or agree."
After The Old Lady reportedly paid Ramsey £400,000-per-week, his time in Turin failed to live up to expectations. He joined Scottish side Rangers on a short-term loan in January 2022 and then signed permanently for French outfit Nice on a free transfer last summer.
Jack Wilshere
Speaking of regrets, former Arsenal midfielder Jack Wilshere has admitted that he should never have left the club to join West Ham United in 2018. Once the Gunners' youngest-ever debutant, it was a dramatic fall from grace for Wilshere, who had shown immense promise during his formative years in north London.
He spent 17 years with Arsenal, but his talent merited far more than the 125 league appearances he ultimately racked up. The former England international departed the Emirates Stadium after enduring several frustrating campaigns, including a year spent on loan with Bournemouth.
Since leaving the Gunners for West Ham, Wilshere’s career really failed to kick-on, having also been released by the Hammers, whilst a short spell back with Bournemouth also ended with the midfielder being without a club. Wilshere announced his retirement from playing football last summer, just over 24 hours after news broke that he had left Danish club AGF. He is now the coach of Arsenal under-18s.
Theo Walcott
Like Wilshere, Walcott burst onto the scene at a very young age, with expectation levels of this particular crop of Arsenal players sky-high with unlimited potential. However, both their careers in north London ended prematurely as the heights promised were never truly reached.
After 12 years at the club, Walcott joined Everton in January 2018 having struggled for playing time during his latter days. Speaking about the attacker's departure at the time, Wenger said he hoped Walcott would stay, but insisted he will have nothing but good memories of the player.
"We speak about cup finals or Champions League games, or the local derbies, where he put in outstanding performances against Tottenham. I just regret what happened, but he didn't play enough recently," Wenger said. "I wish him well and thank him for everything he has done for us. He will always be welcome here."
His arrival on Merseyside failed to kick-start an anticipated break into the top-six for the Toffees, and he was deemed surplus to requirements once more. As such, he returned to where it all started as a 15-year-old when Southampton offered him a Premier League lifeline, but regular action has once again proven hard to come by.
Omari Hutchinson
Most recent of the players on this list, Arsenal were frustrated to lose Omari Hutchinson to Chelsea last summer. The wide player decided not to renew his contract in north London and instead made the switch to the west of the city.
It was a move that left Arsenal supporters frustrated knowing a talented player who had flourished in the youth side had gone to a rival. Mikel Arteta called Hutchinson up eight times to his Premier League side but the then-18-year-old remained an unused substitute.
Since moving to Chelsea he has made his senior debut in the Premier League for the Blues which might come as some justification to the teenager for making the switch. His 22 minutes against Manchester City in a 1-0 defeat however didn’t leave much on the memory.
There’s a real chance too that these few minutes might be tricky to extend upon, both now and in the upcoming seasons. After Chelsea frustrated Arsenal again by hijacking their move for Ukrainian winger Mykhailo Mudryk in January, Graham Potter has a choice from nine forwards when all are available.
Meanwhile, looking over at Arsenal and a pathway for Hutchinson into the Arsenal first team looks much simpler. Reiss Nelson’s contract comes to an end in the summer and behind Bukayo Saka will be just Marquinhos, who could be shipped out on loan again anyway.
Pierre-Emerick Aubameyang
Another attacker currently on Chelsea's books, Pierre-Emerick Aubameyang's Blues career appears to be over before it even started. Signed last summer under Thomas Tuchel, Potter has found it more difficult to find a way of incorporating the former Arsenal man into his set-up.
Aubameyang's four years at the Emirates Stadium were largely productive, having struck 92 goals in 163 games and helping the Gunners win the FA Cup and reach the Europa League final. However, things were left on a sour note as Arteta effectively banished the Gabon striker and shipped him off to Barcelona just over a year ago.
Although he said it was his dream to play for the Spanish giants, he lasted just six months at Camp Nou before Todd Boehly persuaded him to move to Stamford Bridge. Since departing, Arsenal's form has only gathered further momentum, with the young squad poised for an incredible Premier League title, which looked inconceivable 12 months prior.
Santi Cazorla
Santi Cazorla spent a memorable six years at Arsenal where he wowed the Emirates Stadium faithful with his precision passing and eye-catching displays. He became a firm fan-favourite, and his exit was particularly sore for the Gunners fanbase.
However, his injury hell prevented a proper farewell when he left the club on a free transfer to return to Villarreal in 2018. He successfully rebuilt his career in La Liga, but is left with a bittersweet feeling in his mouth as injuries prevented him from achieving all he would have wanted to do in north London.
"I don't know if it's possible or not, but I want to play one more game for Arsenal before I retire. It was a deep regret that I could never have a proper goodbye," he later told Goal.
"Arsenal was the biggest club I ever played for. I'm proud that I was an Arsenal player. I'm especially grateful for Arsenal fans who supported me even after I left the club. I wish I can be part of the Gunners family in the future again."
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