In a candid reflection on his tenure at Everton, former manager Sean Dyche has revealed that the club made ambitious attempts to sign Jack Grealish and Kiernan Dewsbury-Hall during the 2024 transfer window, only to see those deals slip away due to financial and logistical hurdles. Speaking on talkSPORT’s Warm Up with Jonny Owen, Dyche shared insights into the challenges he faced under Farhad Moshiri’s ownership, shedding light on the behind-the-scenes efforts led by former director of football Kevin Thelwell. Now, with Grealish and Dewsbury-Hall thriving under current manager David Moyes at Everton’s new Hill Dickinson Stadium, Dyche’s comments highlight the missed opportunities that could have reshaped his time at Goodison Park, while also offering a glimpse into why Grealish, in particular, has found a perfect fit at the club.
Dyche, who was sacked by Everton in January 2025 after a tough start to the 2024-25 season, explained that the club’s financial constraints and ownership uncertainties made it difficult to secure high-profile targets. “Everybody knows what a big fan I am of David Moyes, he knows I respect him and what he’s done,” Dyche said, acknowledging the success of his successor. “But he’ll know that a lot of them players, we were trying to sign them last year, you can’t get them over the line, whether it’s money [or] you just can’t get the deals done.” Specifically, he noted that Everton had pursued Grealish, who eventually joined on loan from Manchester City in 2025, and Dewsbury-Hall, who signed permanently from Chelsea for £28 million. “Dewsbury-Hall, we were trying for, Jack Grealish, we went in for,” Dyche clarified, emphasizing that while the deals didn’t come close to completion, the club was proactive. “I don’t mean we were close, so before anyone misquotes me, what I mean is we were putting out the calls, Kev Thelwell was going into these situations going: ‘Right, can we?’”
Grealish’s arrival at Everton has been a revelation. The 29-year-old midfielder, whose role at Manchester City diminished under Pep Guardiola, has rediscovered his spark, registering four Premier League assists in just two games during August 2025. His flair and creativity have made him Europe’s top playmaker early in the season, earning him a nomination for the Premier League Player of the Month. Dyche offered insight into why Grealish has thrived, suggesting that Everton’s environment suits him better than City’s rigid system. “He’s a fantastic player and I think he started fantastically well,” Dyche said. “Maybe that bigger fish in a smaller pool suits him.” This echoes the sentiment that Grealish, who shone at Aston Villa before his £100 million move to City, excels when given freedom to express himself, a luxury Moyes has afforded him at Everton.
Dewsbury-Hall, meanwhile, has also been a key addition, bringing midfield cohesiveness and dynamism that aligns with Moyes’ vision. Dyche’s revelation that he targeted the 26-year-old midfielder last year underscores Everton’s long-term interest, though financial limitations under Moshiri’s chaotic ownership stalled progress. “You get in there early and you just keep registering your interest, but you can’t sign everyone,” Dyche explained, reflecting on the transfer market’s challenges. The duo’s impact has helped Everton to a promising start in their first season at Hill Dickinson Stadium, with a 3-2 victory over Wolverhampton Wanderers showcasing their attacking prowess.
The context of Dyche’s tenure adds depth to his comments. Everton’s financial struggles and Moshiri’s ownership issues limited his ability to bolster the squad, contributing to his departure. Moyes, returning to Everton in January 2025, capitalized on a more stable financial outlook to secure nine summer signings, including Grealish and Dewsbury-Hall. Dyche’s remarks carry a hint of frustration but also respect for Moyes’ achievements. As Everton builds on a strong 2025-26 campaign, finishing 23 points above the relegation zone last season, Dyche’s transfer revelation highlights the fine margins in football management. For fans, it’s a reminder of what might have been—and a celebration of the stars now lighting up Merseyside.
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