Unfortunately, the event Tom Naylor’s time at Pompey will be synonymous with in years to come was completely out of his control.
There were a swathe of gutsy, lung-busting, wholehearted performances during his three years at Fratton Park.
Yet that selection decision in the 2019-20 play-offs against Oxford is what substantial sections of fans will think of when reflecting on Naylor’s Blues legacy.
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Having been ever-present when fit, a key cog and – most importantly – captain, Naylor was omitted from Kenny Jackett's plans following the three-and-a-half-month hiatus following the coronavirus outbreak.
There was scarcely a supporter who could fathom the manager at the time’s rationale.
For the biggest two games of the season, his so-called leader who’d never missed a match when available found himself surplus to requirements.
Jackett’s decision might have been more palatable had it been Ben Close who went into the engine room at Naylor's expense.
Instead, it was Bryn Morris – someone who hadn't played for 14 months due to an ongoing hip problem and would be shipped off six months later – who was given a shock recall.
In his memorable post-match interview after the first-leg draw at PO4, Jackett cited his reasons for dropping Naylor as a move for ‘summer football rather than winter football’.
Ultimately, his decision backfired as Pompey suffered penalty shootout heartbreak at Kassam Stadium.
And the moniker of being a ‘winter player’ stuck with Naylor from then onwards.
However, the way the ex-Burton responded to such a hammer blow embodies his south-coast spell.
Many-a player might have sulked and caused a rift after being axed as ignominiously as he was.
Instead, there were no grudges held. In fact, during the first half of the 2020-21 season, Naylor displayed the form of his Fratton career when fizzling home long-range efforts against Peterborough, King's Lynn, Plymouth and Ipswich.
He was low maintenance, high effort and the paragon of a team player.
The fact he won Players’ Player of the Season in 2018-19 – ahead of Jamal Lowe, Matt Clarke and Ronan Curtis – speaks volumes about how much he was valued in the dressing room.
His selfless attitude is why a short while Danny Cowley decided he wanted to keep Naylor shortly after succeeding Jackett in the hot seat in March.
However, an agreement couldn’t be reached.
From the early stages of negotiations, it was clear that Naylor was reluctantly going to give up his captaincy and depart. He wasn’t willing to accept reduced terms.
Approaching 30, Naylor was quite understandably looking for one final long-term contract on a wage he feels will help secure his future with a first child on the way.
That’s something Pompey couldn’t offer given the financial impact the pandemic’s had on them.
Wigan, on the other hand, have a new owner with clout given the ilk of signings they’ve made so far this summer.
Last season was the final chance for the group of players Jackett assembled to deliver Championship football back to Pompey.
It looked like it was going to be achieved at Christmas when Naylor was not only banging in goals for fun but his overall game – passing especially – had improved markedly.
Just like the Blues, however, Naylor couldn't continue his impressive displays at the business end.
His performances, like many of his team-mates, waned as Pompey jettisoned from the summit to missing out on the play-offs entirely.
A failure not to sign a like-for-like replacement in the January window could be a key reason for Naylor's own dip.
He'd not just had a long campaign, but barely missed a minute for three years. Respite was required.
Perhaps those from the outside looking in are surprised that a significant portion of fans aren’t too bothered that their club captain leaving on a free to a League One rival.
But, in truth, it’s because Naylor was a core member of a squad that consistently failed to meet its objective.
There’s been a similar reaction to Ryan Williams, Ben Close and, to an extent, Jack Whatmough after they opted to leave.
Still, the former Derby’s man effort, commitment and dedication could never go faulted.
You can guarantee he will depart gutted he didn’t get help Pompey back into the second tier.