January 21, 2026

Written By Albert Echatah

Chelsea have reportedly made a significant mistake in the summer transfer window according to former Premier League player Jermaine Pennant.

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After a strong finish to the season, Chelsea secured a spot in the Champions League and clinched the Conference League trophy by defeating Real Betis.



Following these achievements, Enzo Maresca’s team has quickly shifted its focus to the transfer market, aiming to strengthen the squad before the Club World Cup.

Chelsea have already made a significant move by signing striker Liam Delap from Ipswich Town, fending off competition from Manchester United. Chelsea’s next priority appears to be reinforcing their goalkeeping options, as first-choice keeper Robert Sanchez had an inconsistent season.

Mike Maignan, AC Milan’s captain, is reportedly a target for Chelsea. However, the clubs are far apart on his transfer fee. Milan values the French goalkeeper at £25 million, but Chelsea is hesitant to pay that amount, especially since Maignan’s contract expires next year.

If Chelsea can’t agree on a transfer fee with AC Milan for a new goalkeeper, they’ll likely rely on their existing squad, which will be strengthened by the return of Djordje Petrovic and Mike Penders from their loan spells.

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However, former Premier League player Jermaine Pennant suggests that Chelsea made a mistake by not pursuing Liverpool’s Caoimhin Kelleher earlier in the transfer window.

Kelleher, an Republic of Ireland international, recently moved from Liverpool to Brentford for a mere £12.5 million, despite having been a target for Chelsea and Tottenham in the past. ‘Kelleher is definitely better than (Robert) Sanchez,’ Pennant told talkSPORT when asked if Chelsea should have considered a move for Kelleher.

‘He never let Liverpool down, and when Alisson did get injured, at no point did you worry because he was so comfortable as a number two. Probably the best number two out there.

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