Chelsea's Summer Gamble Backfires? Sheringham Calls It a Very Strange Move

Sheringham's Take: Chelsea's Move Draws Scrutiny

Former England striker Teddy Sheringham believes Chelsea's summer transfer window decision was a "very strange" one, insisting the Blues' management regretted it almost immediately after execution.

The London club was among Europe's busiest in the close season, spending more than £300m on new arrivals while recouping a similar amount from player sales.

Enzo Maresca introduced new faces such as Joao Pedro, Alejandro Garnacho, and Gouriel Hato, while departures included Noni Madueke, Christopher Nkunku, and Nicolas Jackson, who moved on loan to Bayern Munich with an option to buy.

Although it's early to judge Chelsea's window strategy, their title chances look challenging, with the team sitting five points behind leaders Arsenal after seven Premier League rounds.

Sheringham argued that Jackson's loan was "strange and unjustified," telling Metro: "I thought Chelsea made a very strange decision when they allowed Nicolas Jackson to go on loan to Bayern Munich. The big club always needs a striker who leads the attack and knows exactly what is expected of him."

He added: "Jackson had been at the club for two years, with a improving scoring record. The way he was let go surprised me."

Sheringham noted that Jackson understood Maresca's system and could have helped Pedro settle in faster: "Jackson fit the style and could have helped Pedro integrate, but now they have Pedro and Delap, both still learning the new system, and one is injured."

He also cited Delap's injury timing as evidence of misjudgment: "Delap's injury timing was terrible and showed regret instantly; they tried to recall Jackson, who refused to return, and I think he was right in doing so."

Is this a controversial deal?

Jackson joined Bayern Munich on a one-year loan with a buy option of around £70m if certain appearances are reached. Chelsea even considered blocking the move after Delap's injury, but ultimately allowed it to satisfy the player's wishes, who had expressed a dream of testing himself in the Bundesliga alongside Harry Kane, Bayern's captain and current scorer.

Sheringham argues the club acted rashly, believing Jackson could have become a more mature goalscorer at Chelsea, noting his 30 goals in 81 appearances for the Blues earlier—an impressive ratio given recent instability.

Carlton Cole Defends Jackson

Former Chelsea forward Carlton Cole also voiced surprise at the decision to part with Jackson, insisting the player was valuable for his work rate and discipline. He told the same publication: "I still love Nicolas Jackson. Some criticize him, but he is the kind of striker who runs relentlessly for the team, even if he doesn't always get rewarded or finish every chance."

He added: "He's a hard worker and would be an asset for any team, not the sole star. He deserved minutes, and I have no problem with him seeking more playing time. He's a very good player."

Cole further commented on Jackson's future, saying: "The issue arises when a player tries to be selfish or acts as the main star; that disrupts balance. Jackson's effort is undeniable, but it's not the only problem for Chelsea's attack."

He concluded that replacing Jackson with Joao Pedro is not straightforward: "Pedro is not a direct substitute. Jackson wanted more minutes, and I don't blame him; he's a good player indeed."

In sum, the article makes clear that the transfer window sparked debate: some see strategic risk, others defend players' ambitions and timing. The truth likely lies somewhere between ambition and balance, with fans waiting to see how Maresca's plans unfold in a season already shaping up to be unpredictable.

Punchline 1: If Chelsea's transfer policy were a sniper routine, the crosshair would be on 'glory', yet the bullet lands in 'chaos'—season after season, with a coffee break in between.

Punchline 2: And if timing is everything in football, Chelsea's timing is still warming up the bench—guess the sniper's motto is 'aim small, miss bigger'!