Should Southampton Go For The Forgotten Man In The Tyler Dibling Chelsea Swoop
Sunday, 14th Jun 2026 09:26
When Tyler Dibling joined Chelsea in the summer of 2022 he soon came back to St Mary's, believing his chances would be limited at Stamford Bridge, but the fellow Southampton academy starlet who also went to the Blues did not heed the wrning, 3 years on he may regret that decision.
Back in 2022 the Saints academy side had two outstanding talents, Tyler Dibling was of course one and Jimmy Jay Morgan the other, a the age of 16 they had important decisions to make regarding their futures as the big clubs circled.
When Dibling decided that he too would go to Stamford Bridge in the summer of 2022,, it was a blow for Southampton to have lost such a talent, but there was a twist to the tail, within weeks, Dibling had decided that Stamford Bridge was not to his liking, he could not see a path to the Chelsea first team and he felt his career would be best served at Southampton, where he had a realistic chance of playing for the first team.
In fairness to Chelsea they did not stand in his way and allowed him to rejoin Saints, the official line being that he was suffering from home sickness, something that did have some truth in it.
Jimmy Jay Morgan reached his 17th birthday and he too had a decision to make and opted to join Chelsea, prolific at U18 level, Morgan certainly had an eye for goal and there were those at Staplewood who thought he was a bigger talent than Tyler Dibling.
Like Dibling he was tempted to Stamford Bridge by a lucrative contract, one far bigger than Southampton could offer him and with built in clauses regarding increases & bonus's etc.
From a financial point of view you could understand why he wanted to go and put money before career progression and now it seems that has been the case.
Whilst Dibling steadily learnt his trade and made the Southampton first team, earning a big money move to Everton, Jimmy Jay's career has not got very far at Chelsea.
In his first season he did ok but not brilliantly, he was nowhere near the Chelsea first team squad and for the second half of the 2024/25 season he was loaned out to League Two Gillingham, he must have had a wry smile as Tyler Dibling featured for Saints in the Premier league.
It didn't go well at Priestfield, just 10 starts, 6 appearances from the bench plus 5 games where he didn't get on the field, just two goals to his name.
Back to Chelsea last summer, he found that he wasn't in their plans and was shipped out on another loan, this time to League One Peterborough.
After a fairly decent start to his career at London Road, a goal in each of his first 3 games was followed by only 3 goals in the next 20, before another little burst of scoring where he hit a 5 game scoring spell.
He would end the season with 12 goals in his 34 League Two appearances, not form that would have impressed Chelsea
Now back at Stamford Bridge and aged 20 he finds his career is at a crossroads, with a year of his four year contract left, Chelsea are keen to get him off the books and are looking at trying to get a fee for him now.
Thus he is being linked with the likes of West Bromwich Albion and Sheffield United who are vying to sign a player that according to transfermarkt is valued at around £350k.
I think that is a little low and that he will fetch a million or two in a Dutch auction.
There is no doubt that Morgan was a talent at St Mary's, he scored prolifically at U21 Academy level, even at Chelsea, he has shown that he can score at League One level, so the big question is should Southampton consider resigning him.
With Ross Stewart leaving there is space up front, would Morgan be a wild car option for a fairly low transfer punt ?
Of course there are those who would point at former Saint Dom Ballard who hit 23 goals for Leyton Orient in League One last season and suggest that we go for him if we are going to bring back a prodigal son and there will be those that would say that players coming back for a second spell rarely work.
I don't know enough about Jimmy Jay Morgan to give an educated guess on this, but I would say that if he is going for a million he could be worth a punt based on what he achieved last season, he is a year younger than Dom Ballard so is still developing.
So what do you think, could he do a job for us next season ?
All Photos Via Reuters
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