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When Wayne Rooney left since Paul Gascoigne.
559 United appearances and 253 goals later, he's back at his boyhood club under a new set of circumstances.
He joins Everton at a time when the club appear to be in transition. They're always a sides who are capable of qualifying for the Europa League via their league position, and anything less would be seen as a disappointment. But at the same time the task of finishing in the top four and qualifying for the Champions League has always seemed out of the question.
Now, with new financial backing and plans for a new stadium the club could well be in the up.
Though breaking into what is now a “big six” group of teams which contains Rooney's former club United, Manchester City, Chelsea, Tottenham, Arsenal, and local rivals Liverpool would be difficult, it seems that plans are in place for the club to aim to compete at this level, rather than just accept a sixth or seventh place finished as the best they can do.
The Toffees will also hope to end their 22-year wait for silverware. Should they qualify for the Europa League group stages via the qualifying round and play-off, they'll find themselves n three cup competitions.
The challenge for manager Ronald Koeman would be to win at least one trophy while also challenging in the league. Anything lower than last season's seventh place finish would be a disappointment and questions would be asked of the manager.
Getting the best from Rooney in the latter stages of his career could be the manager's biggest task, but if it's a project he succeeds with then the rest of it could fall into place a lot more easily.
The club have spent just under £100 million so far this season and brought in six players who can challenge for first team spots. They'll want to slide these new arrivals comfortably into the existing setup rather than shoehorning them in, and the role for Rooney could dictate how smoothly the new look team operates.
Despite being only 31 years old, Rooney is in the twilight of his career at the top level. Having played regularly since the age of 16 he has the experience, but also the physical fatigue, of a player older than his years.
Since his return to the side he's been used by the manager in a number of attacking roles, including all three slots in a front three. More often than not he will play at least two positions in one game as other players enter the fray from the bench or the manager makes tactical changes.
In the only competitive match so far, against Ruzomberok in the Europa League third round qualifier, he started the game as the lone striker with two wingers either side of him.
Whilst he showed plenty of willing and got into some good positions, there was a lack of cutting edge to his play, which reflected that of his team mates. One good chance was scuffed with the bottom of his boot, and the combination of lack of playing time last season and the break before pre-season meant that he was just a few moments behind the play. But, to be fair, he wasn't the only one.
Everton will hope that this is indeed merely a lack of match sharpness and not something more long term, but there were promising signs in the second half of these game when he took up a new position.
The second half introduction of new signing Sandro Ramirez, who replaced right winger Dominic Calvert-Lewin, saw Rooney drop to the right while the Spaniard used his pace to stretch the play up top.
It was here that Koeman may have learnt that the best role for the new-look Rooney would be behind pacy players, rather than in front or in the middle of them. On the right wing he played the role of wide playmaker, drifting inside and dropping back into the midfield to help build the play.
In this second role he looked more comfortable, more involved, and at his most productive. Koeman is fond of having a playmaker or midfielder coming in from the wings, and it's a position which has been occupied by Rooney's fellow Liverpudlians, Ross Barkley and Tom Davies at times during last season.
Should Gylfi Sigurdsson eventually sign from Swansea you could also see the Icelander playing in this role, as well as the attacking midfield position which on this occasion was occupied by another new signing, Davy Klaassen.
After creating a few chances Everton eventually got their goal through Leighton Baines. Though the strike only found the net courtesy of a lucky deflection, the Everton attack had done enough to make the Slovakian's defence more ragged and disorganised.
The build up to the new season will be a steep learning curve for the manager as well as the new players, and the sooner he finds out what Rooney is still good at, the better.
There's a risk he could become a jack of all trades but a master of none in the Everton attack, but this roaming role from outside, whether it be from the left or the right seems like the best option so far.
Even at 31-years-old, Rooney still has plenty to learn as he looks to enjoy a successful end to his own career at the top level, while also trying to bring a trophy to his beloved club. What Rooney learns about himself in the coming weeks and months will be important, but what Koeman learns about his new player could be even more so.