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FLW's Pompey fan pundit believes that the decision to allow Conor Chaplin still shocks fans to this day

This article is part of Football League World's 'Terrace Talk' series, which provides personal opinions from our FLW Fan Pundits regarding the latest breaking news, teams, players, managers, potential signings and more...

Portsmouth's decision to let striker Conor Chaplin leave on a free transfer in 2019 has been identified as one that still shocks their fans to this day, especially given his exploits since leaving the south coast.

Chaplin joined the Pompey academy at the age of six, and progressed up the youth ranks at Fratton Park to make his first-team debut for his boyhood club in December 2014 while they were in League Two.

He soon broke into the senior side for good, and was unable to ever really nail down a starting spot under Paul Cook, but did help Portsmouth win promotion back to the third-tier in 2017 as champions and was highly regarded as a player to keep an eye on for the future.

Chaplin helped the club establish themselves in League One under Kenny Jackett, but was loaned out to fellow third-tier side Coventry City in August 2018, with a view to a permanent deal, and so left Pompey for good in January 2019 to join the Sky Blues.

Fan pundit outlines Portsmouth's Conor Chaplin decision as a shock

Chaplin's career has flourished since his Pompey departure, after he did well enough at Coventry to earn a move to Championship side Barnsley that same summer, and has since impressed in the third and second-tier with Ipswich Town.

The 27-year-old recently celebrated promotion to the Premier League with the Tractor Boys after playing a key role in their success under Kieran McKenna, and FLW's Pompey fan pundit Miltos Ioannidis identified allowing him to leave over five years ago when we asked him for a decision made by the club that still shocks him to this day.

"I think the whole Conor Chaplin saga is definitely right up there," he told FLW.

"To this day, it baffles me how, not only did we allow him to leave on a free transfer, but our manager at the time, Kenny Jackett, thought he wasn’t going to be good enough for us.

"He sold Chaplin to another team as a result, and it was one of many questionable decisions made by him that I don’t understand.

"We’ve seen the things that Conor has gone on to do after he left Portsmouth, and what happened to Kenny Jackett’s Pompey side as well.

"The decision still shocks and baffles me to some extent, even to this day."

Chaplin chose to leave Portsmouth for his career

Chaplin's career has gone from strength-to-strength since leaving Portsmouth, with recent exploits at Barnsley and Ipswich proving that they were wrong to let him leave, but Pompey seemingly had little choice regarding his departure.

He had struggled for consistent starting berths since breaking through at Fratton Park, and his minutes became limited even further after promotion to League One, as he made just 11 league starts in 2017/18, and featured just twice off the bench in the final 10 games of the season.

That lack of game-time saw Chaplin ask then-boss Jackett for a move that summer, and so he joined Coventry to bring his 15-year association with Portsmouth to an end, which he explains further in an excerpt from 2020 book 'Pompey: The Island City With A Football Club For A Heart', via Portsmouth News.

He said: "Pompey is my club, I have always been there. At school I was 'Conor who plays for Pompey', it’s the club where I spent 80 percent of my life, which is frightening when you think about it.

"The worst thing in the world was leaving, but it was a decision I had to make and don’t regret it.

"Kenny wanted me to stay, he tried everything he could to get me to remain, but the decision I made was solely for my career.

"I needed to leave and play football. I’d speak to friends and family to express my worries, I was so scared of ending up being one of those kids with such big potential yet never fulfilling it.

"Pompey is an unbelievable club, an absolutely unbelievable club. I would rather have continued there, but that wasn’t to be. There are no regrets about leaving, it has turned out to be the right decision."

Chaplin has bagged a myriad of individual awards in recent years, including the League One Golden Boot for 2022/23 as Ipswich were promoted to the second-tier, and the club and league's Player of the Year award for the same season.

He netted 13 times in 44 Championship outings last season as McKenna's side clinched a consecutive promotion to the Premier League, and now, at 27-years-old, will surely have no lingering regrets about leaving Pompey all those years ago.