Transfer windows being a time of jumbled up gambles, opportunities and big decisions, it must feel like half a lifetime ago that Aaron Ramsey last found himself in the thick of it all. The previous time, when he signed for Arsenal aged 17, his football shirt hung off a slender frame beneath a teenage haircut and unsettled complexion. He was just a boy looking at a big wide world of football out there, fresh from an FA Cup final appearance with Cardiff, eager to take on the next challenge.

It is fair to say that as decades spent at a big club go, this has been quite a complicated one. He arrived at a place with fresh memories of winning the league unbeaten and reaching the Champions League final, who had recently moved into a more roomy and plush stadium, who spun a dream about winning more with the best young players they could find. But his early years at Arsenal would be marked by the clocking up of years without a trophy, and the latter ones – rescued by a string of FA Cups he would embellish with matchwinning goals – became entangled with the difficult final act of Arsène Wenger’s tenure. Ramsey has been a constant throughout a period when pressure seldom let up, and he has played in his own way – trying things, working hard, never shy of commitment, seldom happier than when executing a dainty flick or spotting a well-timed run into the box.

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The essence of the player Ramsey has grown into – a player who is coveted now as a soon-to-be free agent by a cluster of major clubs with Juventus looking set to conclude the deal shortly – showed itself right from the very start. Introducing himself to Arsenal in a friendly at Barnet in the pre-season of 2008-09 the young Welshman exhibited every trick in his book. Dinks and pirouettes, dragbacks and turns, a part of Ramsey’s makeup has always been committed to footballing art for footballing art’s sake, whether it is the right time or not, the most efficient move or not, the risky decision or not.

Wenger, who had made it his personal business to sign Ramsey by inviting the player and his family out to Switzerland while he was on TV duty at the 2008 European Championship to sell the idea of a move to Arsenal, watched this skills showcase from the dugout. Let’s just politely say it looked like he wasn’t all that thrilled. Ramsey’s unshakeable commitment to the joy of the trick would become both his shiniest strength and at times a risky and frustrating foible. And so the mission to best harness Ramsey’s qualities within the team framework began.

In his second season he was growing in influence when his progress was horrifically curtailed by a shocking injury suffered in a foul by Ryan Shawcross at Stoke. A double fracture of his tibia and fibula in his right leg became one of the defining moments of his career. Having seen Abou Diaby and Eduardo afflicted with similarly worrying breaks because of heavy tackles, Ramsey’s injury carried big emotional weight. Would he recover fully, in a way that his predecessors struggled to do? There were other issues, not least the peculiar “rivalry” that sprung up between Stoke and Arsenal in its aftermath. Ramsey was routinely booed in matches at the same venue. As a person he is not an attention seeker, so this element of the football environment never made much sense to him.

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Fortunately for Ramsey, his rehabilitation went safely enough for his career to pick up unfettered, enabling him to enjoy some personal highlights he will always cherish. Twice he was the matchwinner for Arsenal at Wembley in the FA Cup finals of 2014 and 2017. For Wales he has felt the joy of international competition, and his excellence particularly at the 2016 European Championship in France shone for all to see.

Facebook Twitter Pinterest Aaron Ramsey in action for Cardiff in 2008. Photograph: Shaun Botterill/Getty Images

Moving on from Arsenal is something he will take in his quiet stride. Away from the game Ramsey remains quite old fashioned in the way he doesn’t care for being flash or getting carried away. A family man who has stayed close to his old friends and will gladly go off to Glastonbury without wanting any special experience, just to go with the normal flow in a big crowd enjoying some music and camping, the way he has handled this strange half a season under Unai Emery has been admirable. Pushed on to the bench once Arsenal withdrew his contract extension, he has said nothing, got on with the job with professionalism and made himself available to play to his best whenever called on.

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Arsenal are losing the highest scoring central midfielder in their history for nothing, a hangover from the contract strategies run by Ivan Gazidis, which leaves the wage bill restricted for some top players while others remain on gargantuan deals. Ramsey’s freewheeling spirit on the pitch, always at his best when playing with positional freedom and less inclined to adhere to positional discipline, did not perhaps tick as many boxes for Emery as he was expecting when he arrived last summer and announced quite quickly how important it was that Ramsey stayed.

The club played their hand. Now they have to go back into the market when Ramsey says his farewell to replace those goals and assists from midfield. Less simple is replacing all the club knowhow he has accumulated. As Ramsey knows from the summer he joined in 2008, sometimes a transfer has to be more about hope than expectation. Ramsey arrived in a mixed bag of a window: Wojciech Szczesny came into the youth team. Samir Nasri, then 21, was brought for technical spark and attitude. Few remember Amaury Bischoff, one of those regarded as a cheap long shot on the off chance he might turn into something. Few dare to remember Mikaël Silvestre, a veteran who made it look entirely understandable why Sir Alex Ferguson felt the time was right to give him away.

Ramsey turned out to be the best deal by miles.