Newcastle's chances of keeping Bruno Guimaraes already looked fairly slim before Eddie Howe's departure.
News of Howe's exit, following Wednesday evening's 4-1 friendly defeat at Championship side Bristol City, poses huge questions about the Magpies' project and their potential prospects for the coming season.
German replacement Matthias Jaissle, though his arrival is yet to be formally confirmed, now has a major fight on his hands to convince club captain Guimaraes to stay.
The Brazilian has two years remaining on his contract, which also includes a 12-month extension option, at St James' Park but the all-action midfielder has already reached a verbal agreement on personal terms with the Premier League champions.
Now the landscape for keeping Guimaraes on Tyneside looks even more complex for Newcastle.
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Firstly, it's no secret he had a great relationship with boss Howe. The Englishman brought the 28-year-old to the club and together, they have made Newcastle history.
Together, they qualified for the Champions League on two separate occasions and also ended the Magpies' gruelling 56-year wait for silverware in 2025 as they defeated Liverpool in the Carabao Cup final at Wembley.
On the back of major departures, Howe was likely one of the only few reasons - outside of Newcastle driving a hard bargain - why Guimaraes may have eventually stayed.
Secondly, it's important to analyse the context behind Howe's departure. Recruitment has been underwhelming this summer. There has been a drastic shift in strategy and Ross Wilson has decided to go big on signing young prospects.
But having lost Anthony Gordon, Sandro Tonali and Kieran Trippier - three key cornerstones of the dressing room - Newcastle requires more quality and experience.
There is a chance - and this is of course not confirmed - that Guimaraes may feel disappointed by Newcastle's transfer business during what feels like a huge window for the club after a 12th-place finish.
Thirdly, having watched important team-mates leave, he may feel like he's taken the club as far as he can. A few years back, a title charge did not feel lightyears away if Newcastle continued to improve and strengthen.
He has nothing left to achieve on Tyneside and he's given absolutely everything for the club. Perhaps that won't be popular amongst supporters but at 28, he is well within his rights to consider a new challenge.
When Arsenal come calling, a club capable of competing for the biggest prizes, it's easy to see why that opportunity may appeal.
At this stage, it's probably in Newcastle's best interests to agree a deal despite the fan frustration that will follow and to utilise that cash on signing extra quality.
The situation is a mess and unfortunately, it all looks too damaging for the team's image at this moment in time.
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