A tale of two boyhood Blues is set to play out against the back drop of Goodison Park ahead of Everton's Europa League third round qualifier against MFK Ruzomberok.
One is set to embark on his second debut - and first ever European appearance - for the Toffees after 13 years away with Manchester United, while the other is set to bring an end to his 12-year association in some capacity before the end of the transfer window.
Wayne Rooney and Ross Barkley are at polar opposites of their respective playing careers, and the latter's decision to embark on a 'new challenge' away from Merseyside may draw certain parallels with that of his veteran and current - for now at least - team mate.
However, Barkley's increasingly likely Everton departure will be anything like Rooney's own acrimonious £27m move down the M62 to Manchester United. It is, in fact, much more in danger of replicating those youth products who really did find that the grass isn't always greener away from L4.
Jack Rodwell, Francis Jeffers, Michael Ball, James Vaughan, Shane Duffy. All recent examples of talented stars within the Blues' academy that, for whatever reason, seemed destined for greatness at Goodison but eventually left and failed to live up to the hype.
Their reasons for leaving were as varied as they come, in truth, but the end result was always the same: vast potential that wasn't turned into the true ability that could have been reached.
Barkley, who rejected the offer a lucrative new deal to extend his stay, is under threat from treading a similar path to those that came before and, in turn, a far cry away from the riches that Rooney was laden with during his long Old Trafford spell.
The 23-year-old has truly only enjoyed one scintillating campaign as a professional, with the 2015/16 season seeing Barkly rack up 12 goals and 11 assists in 48 games.
His other seasons in royal blue make for lacklustre reading - a further combined 15 goals and 17 assists registered in another 131 matches across four other terms - and prove that his end product is not all it's cracked up to be.
It is this lack of consistent end product that saw manager Ronald Koeman regularly trot out such an excuse for his side's inability to secure the wins necessary to finish higher in the Premier League standings last season. Couple that with the Dutchman's struggle to get the best out of Barkley, whether that be with an arm round the shoulder or a blast of the hairdryer treatment, and it's easy to see why Koeman ran out of patience with Barkley.
The writing was on the wall for the midfielder when Koeman forked out £24m on Ajax captain Davy Klaassen, and his unrelenting pursuit of £50m-rated Swansea talisman Gylfi Sigurdsson only further fanned the flames that Barkley's days were numbered.
The romantic return of Rooney - yet another star who could play in Barkley's favoured position on the field - added further nails into his Everton career's coffin, and demonstrates a marked difference in their ambitions in helping to haul the Toffees back to the top table of English football.
Cannot get my head around Ross Barkley turning down a lucrative contract at his newly ambitious boyhood club. Madness. Sell him and move on.— Joe Strange (@joe_strange) July 26, 2017
So what of this new challenge that Barkley is desperate to undertake?
A transfer to a top six side would certainly be seen as a step up by the man himself, but his first-team chances would be greatly diminished wherever he rocked up at. North London rivals Arsenal and Tottenham are the only teams above who are reportedly monitoring his situation, but no official offers have been forthcoming.
Barkley wouldn't make the first-choice starting lineups at Chelsea, Manchester City, Manchester United or - dare we say it - Liverpool, and nor would he at Spurs. With the Gunners maybe, but as a regular starter? Not likely.
Newcastle United and West Ham would definitely be steps down for the England international, despite what those club's fanbases would say, and the only other viable option of a move abroad would arguably not appeal due to Barkley's homebody personality.
Barkley is at a crossroads in his playing career, and whichever path he takes is presumably going to lead him down a route that will only end in disappointment.
Ross Barkley in slow, poor decision shocker.— GrandOldTeam.com (@grandoldteam) July 26, 2017
Rodwell and Jeffers showed that switches to the footballing elite will stunt a player's growth. Vaughan and Ball also proved that injuries and failing to fulfil your potential will see a player fall to the periphery of the beautiful game.
Barkley had his chance to help lead Everton back into the big time, and his decision to walk away may only prove to be the wrong conclusion to reach.
One boyhood Blue returns; another will depart. In Barkley's case, there likely won't be a trophy-laden spell away before a fairytale return akin to Rooney but a career filled with questions of 'what could have been'.