Ipswich Town & Sheffield Wednesday must envy when Charlton Athletic struck Crystal Palace transfer gold | OneFootball

Ipswich Town and Sheffield Wednesday were interested in Jesurun Rak-Sakyi during his loan spell at Charlton Athletic

Ipswich Town, Sheffield Wednesday, and Charlton Athletic have all experienced varying ups and downs in recent years.

The Tractor Boys went on an incredible journey when Kieran McKenna steered them to back-to-back promotions from League One to the Premier League.

However, Ipswich lasted just one season in the top flight, and were relegated back to the Championship alongside Southampton and Leicester City in 2025.

Meanwhile, Charlton ended a five-season spell away from the second tier by defeating Leyton Orient in the League One play-off final.

Sheffield Wednesday tasted their own third-tier play-off glory in 2023, and subsequently secured Championship survival under Danny Rohl's stewardship.

However, by the summer of 2025, the Owls were in financial turmoil thanks to former owner Dejphon Chansiri, which prompted Rohl to leave Hillsborough alongside several star players.

Wednesday were relegated to League One during their time in administration, while the South Yorkshire outfit, Ipswich, and Charlton have all had varying degrees of luck in the transfer market over the years.

Sheffield Wednesday and Ipswich Town were left envious of Jesurun Rak-Sakyi's Charlton Athletic exploits

One of the Addicks' best transfer deals in recent years came when they signed Jesurun Rak-Sakyi on loan from fellow South London outfit Crystal Palace in the summer of 2022.

When the Valley outfit signed the winger, then Charlton boss Ben Garner told the club website: "Jes is an exciting addition to our squad. He is a talented player who adds to the creativity and attacking threat that we have.

"We are very much looking forward to working with him, and hopefully he can have a big impact this season."

The Addicks sacked Garner in December 2022, when they sat just 17th in League One, but the former manager's decision to acquire Rak-Sakyi was a great call.

He lit up the third tier by notching 15 goals and eight assists in 43 league appearances, helping the South London outfit to a 10th-place finish.

Rak-Sakyi also made four EFL Cup outings, producing one assist in the process, as Charlton impressively reached the quarter-finals, where they were beaten by Manchester United.

Thanks to his efforts in both the cup and the league, the winger was voted by Addicks fans as the supporters' player of the season for the 2022/23 campaign.

Meanwhile, as reported by the East Anglian Daily Times, Ipswich and Wednesday had both eyed loan moves for Rak-Sakyi ahead of the 2023 January transfer window.

The report added that Palace had a recall clause, meaning that the winger could have returned to Selhurst Park before being deployed elsewhere.

However, Rak-Sakyi instead stayed at The Valley, leaving then League One rivals Ipswich and Wednesday envious of his performances in South London.

Both the Tractor Boys and the Owls ultimately won promotion from the third tier that campaign, but McKenna's side may believe that they could have beaten Plymouth Argyle to the title if they were able to sign the ace who was then on loan at Charlton.

Meanwhile, the South Yorkshire outfit could think that they would have had enough to beat Ipswich to an automatic promotion spot if they signed Rak-Sakyi.

Sheffield United saw a glimpse of what Charlton Athletic got from Jesurun Rak-Sakyi

The winger's performances in League One for Charlton suggested that he had what it took to adjust to the Championship.

Therefore, Sheffield United signed him on loan in the summer of 2024, having just finished bottom of the Premier League, with Blades boss Chris Wilder telling the club site: "He's still young, and has lots to learn, but he has real talent, and he's someone who has the ability to get the punters off their seats.

"Again, like some of the other players we've taken this summer, he's someone we'll enjoy working with."

As Wilder expected, Rak-Sakyi did produce moments of excitement in Sheffield United colours, such as his brace in a 2-0 win over Luton Town on his 22nd birthday in October 2024.

The winger's return of seven goals and two assists in 35 Championship appearances helped the Blades reach the play-off final, where they were beaten by Sunderland, but he wasn't as prolific for the Bramall Lane club as he was for Charlton.

Ultimately, though, it was then League One rivals Ipswich and Wednesday who were left the most jealous of Rak-Sakyi's Addicks performances.