Although progress is being made to sign Pierre-Emerick Aubameyang and Chelsea are still hopeful of agreeing a deal for the Barcelona forward that suits all parties, there is a giant red flag for the Blues, and it's one that could see them follow on an old path.
The Gabonese forward is the main remaining target for Todd Boehly with Wesley Fofana all but a done deal. Aubameyang became a rogue option earlier this window as Chelsea's fluid-front three started the season slowly, with only Raheem Sterling scoring in the opening four matches.
With the departures at the front of the pitch as well Thomas Tuchel has seen a massive overhaul of his squad this summer, but needs more names if his side are to be competitive to the extent demanded by the German. Aubameyang, seen glowingly by Tuchel due to his previous relationship at Borussia Dortmund, is the first choice for the Blues' boss.
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With an astonishing record in Germany, Aubameyang has followed up his 56 league goals in 63 matches in the Bundesliga with 22 in consecutive Premier League campaigns too. His pace, clinical finishing and ability to move across the front line all make him an attractive proposition for Boehly and Tuchel. But there is a big point to consider. His age.
At 33, Aubemayang's best playing years are likely behind him and, although he was part of a struggling Arsenal side, he only managed 14 goals in his last 43 matches. This has somewhat been accounted for given his impressive half a season in Catalunya, scoring 11 and assisting once in 17 matches.
This doesn't discount the fear that even on a short term deal, Chelsea are getting themselves into somewhat of a tangle. They have tried short-term forward options before: Radamel Falcao, Alexander Pato and Gonzalo Higuain all spring to mind. And there is a sense of deja vu in entering serious negotiations for Aubameyang.
Chelsea have already become tied down to underperforming players on long deals and held onto to too many players way past their expiry date. There is certainly an argument to make for Willian and Pedro being two of this kind, and it's a precedent set that Aubameyang could feasibly hit as well.
Willian, who came in for harsh criticism during his final two years at Stamford Bridge, was a favourite of both Frank Lampard and Maurizio Sarri due to his consistent availability. As Lampard entered his second year Chelsea were willing to extend his contract by one year as he entered his 30s. This is a strategy that has already been changed under Boehly and Chelsea more recently with Thiago Silva still playing as he approaches 38 and Cesar Azpilicueta receiving his own two-year extension despite being 33.
Willian felt that his seven years in London deserved a faithful offer and went to Arsenal instead, where Chelsea were proved right as the winger lasted just one of his three contracted years and played the least minutes he had in a Premier League season.
When Willian played his final year at Chelsea he was 30. Pedro was slightly older at 32 by the time Lampard let him go in the summer of 2020. Both players were younger than Aubameyang would be if he was to sign in the final days of the window.
It's not that there are necessarily fitness concerns. Much like Willian and Pedro, Aubameyang has been readily available for selection for most of his career. He has never missed more than three matches for a physical injury, and played more than 29 league matches in nine of his 14 professional seasons.
The issue is that on high wages, as David Ornstein reports that he would be on, and a possible two year deal with an option of a third - another reported structure - Chelsea don't want to tie themselves to a player that could be 36 by the time his contract expires.
Silva is a complete outlier in world football, playing at a world class level in the Premier League into his late 30s, and even Cristiano Ronaldo's goal scoring has dropped off as he grows older. Aubameyang might be able to stay fit, but for the money, at least £15m though any deal would likely cost more than £20m, can Chelsea risk hoarding another senior player into their squad? It's something that Tuchel might want now, but just as he plans to move on more of his attackers, years down the line it might not be.
Wilfried Zaha is in a similar position. Although he is 29 and playing at his peak right now, registering three goals already this season on top of 25 in his last two campaigns, the Ivorian would demand a high fee to lure him away from Crystal Palace, even with just a year left on his contract. He would also need high wages and a decent number of years on a deal.
This again poses the question as to if the short term improvement of having Zaha this season would be worth the possible struggle to offload him in three years time when he is 32. It is a tough one to work out fully. There are so many unknowns and Zaha, who has already played more than 400 senior matches, has remained consistent throughout his career, putting up more than 29 matches in 11 of his 14 senior seasons as well. He is a player on form that is dynamic and clinical, but signing a proven 29-year-old in Lukaku backfired last summer and Chelsea can't afford to keep doing it.
Tuchel wants to add a mixture of experience to his side this summer, so to determine the suitability of Zaha and Aubameyang this window, if they are seen as last resorts then there's a reason for that and it would wiser to steer clear and work with the current squad, maintaining the long-term goal.
With a director of football in place it's hard to see Chelsea sanctioning the deal for Aubameyang. That should be a warning for Boehly now. Zaha is a different question, but it has it's own intricacies.
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