Everton began their preparations for the 2021-22 season under their latest new manager, Rafael Benitez, in squad- and wage-trimming mode and they began the summer's transfer business in the second half of July 2021 by signing Andros Townsend and Asmir Begovic on free transfers before jettisoning the high-earning Bernard and acquiring winger Demarai Gray for around £1.7m.
The Birmingham-born winger had been linked with the Toffees in 2016 before he left his hometown club for Leicester City where he made 169 appearances without ever convincing successive Foxes managers that he was worthy of a regular starting role.
A pacy, direct wide player, Gray was picked up with six months left on his contract at the King Power Stadium by German outfit Bayer Leverkusen in January 2021 and signed to an 18-month deal.
He scored on his Bundesliga
and made 12 appearances in all before Everton activated a clause in his contract during the close season to bring him back to the Premier League.
Then 25, he signed a 3-year contract that would keep him with the Toffees until 2024 but there was an option for the club to extend it by a further year.
Gray settled quickly, scoring 3 goals in the first 4 Premier League
games that underpinned a good start for Everton under new Benitez but a serious reverse in the fifth game, at Aston Villa,
saw the goals dry up and, while he made a couple of assists in the
ensuing months as the team's good early form evaporated amidst a perfect
storm of injuries to key players, the goals would not return until
A potentially important strike against Liverpool proved to be poor
consolation in a horrendous final scoreline in the Goodison derby amid a terrible run of six
defeats but, in added time at the end of the very next game, Gray came up with a
rocket from outside the box to beat Arsenal in spectacular fashion.
Unfortunately, that would be his last Premier League goal of the season as Gray struggled to rediscover his early-season form under new boss Frank Lampard and his contributions to the battle against relegation that season were erratic. However, he would make one telling assist in the dramatic
penultimate game of the season against Crystal Palace in a raucous Goodison Park. It was from his late free-kick that Dominic Calvert-Lewin powered home the header that guaranteed the Toffees' top-flight survival with a game to spare.
Everton would struggle again in 2022-23, though, with Calvert-Lewin spending long spells on the sidelines and the likes of Gray, Anthony Gordon and Neal Maupay tasked with finding the goals to keep the club out of the bottom three.
Gray fared slightly better than most in the Blues' side and he was top scorer, albeit with just five goals in all compeitions, by the time Lampard was sacked in January 2023 with Everton in the relegation zone and looking ominously vulnerable to falling out of the top flight.
It took a few games but the winger was able to reclaim a starting role in the team under Everton's latest managerial appointment, Sean Dyche, leading the line once more in Calvert-Lewin's continuing absence as the Toffees once again escaped the drop, this time on the final day of the season.
That summer, Demarai switched his national allegiance from England to Jamaica and was named in their 2023 Concacaf Cup squad. He had played at youth level for England earlier in his career and even been called up to the senior squad once but was never capped.
However, it memerged late in the summer 2023 window that Gray's relationship with Dyche had soured, either because of a perceived lack of application on the player's part or the fact that he had actively been trying to secure a move away, perhaps because he felt he didn't fit in the new manager's plans.
Neither interest from Crystal Palace nor Fulham bore fruit so his best avenue out of Goodison was to follow the exodus to Saudi Arahia where first Al Shabab and then Al Ettifaq had shown a keen interest in his services. Eventually, it was the latter club from the Saudi Pro League that landed him and he linked up with former Aston Villa boss Steven Gerrard in an £8m deal in September.
His departure was accompanied by a public exchange of comflicting words by the player and Dyche over the circumstances that drove him away but for the club, it meant that with Gray, Alex Iwobi and Neal Maupay all leaving that month, the squad was worryingly threadbare.
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