Arsenal's deal to sign Nuno Tavares from Benfica certainly hasn't gone to plan for the north London club and there could be yet more issues stemming from the transfer.
Tavares, 23, joined Arsenal from the Portuguese side in 2021 in a deal worth around £8m.
He managed 28 appearances in all competitions for the Premier League club in his debut season in English football.
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But he was loaned out to Marseille last season after being deemed surplus to requirements at the Emirates.
It followed reports that he often 'annoyed' Arsenal boss Mikel Arteta in training.
After a bright start at Marseille, things quickly went downhill for Tavares in France.
Similar reports to his time at Arsenal claimed the full-back had frustrated Marseille coaching staff with his behaviour in training and inability to follow simple instructions.
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Nevertheless, he made 39 appearances in all competitions for the French club, scoring six times, to help them finish third in Ligue 1.
He is now set to return to Arsenal ahead of the 2023/24 campaign but more problems could be on the horizon.
Agent 'suing' Benfica over Tavares deal
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Reports in Portugal claim that agent Cesar Boaventura, who helped broker the defender's move from Benfica to Arsenal, has taken legal action against the Lisbon side - demanding a payment of €984,000 (£846,000).
Portuguese outlet Record (via Sport Witness) claim Boaventura, who is currently under house arrest, has named several witnesses in the case including Arsenal sporting director Edu Gaspar, who handled the Tavares transfer on behalf of the Gunners.
Benfica president Luis Filipe Vieira, club director Rui Pedro Braz and and lawyer Celia Fale have also been named as witnesses, according to the report.
Boavista claims to be owed around €800,000 (£687,000) from the transfer and has added interest on top fee, to reach the final figure of €984,000.
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SPORTbible has contacted Arsenal for comment.
Featured Image Credit: AlamyTopics: Arsenal, Football, Premier League, Benfica, Portugal