When Ancelotti did a runner on us, and then we hired Benitez as his replacement! I think if Carlo stuck around we'd be fine, but when he left we were snookered good and proper.
Benitez drove out players like James Rodriguez and Lucas Digne, and that whole period created this horrible atmosphere within the club and amongst the fanbase.
There was lot's of factors that caused this mess, but Carlo leaving was the final knockout blow imo.
Ultimately while the money spent under Carlo has contributed to this issue the key mistake of the Moshiri era was appointing Benitez.
There's been a few though.
As the OP
@Toffee in Jandals says, that 2017 summer was the one where we far overspent on crap. However, that summer didn't impact us FFP wise at first.
The next mistake was Brands' failure to get in key targets for Silva in 2019. At the same time, this is when Moshiri really started medalling. I think before then, Bernard had been the only signing he'd pushed for, and let's face it, 2018 Bernard would walk into this team now.
The appointment of Carlo might in hindsight have been the wrong thing to do, with Moyes right there. Moyes wouldn't have needed money and he'd have steadied it, and been able to build long-term. But I can't blame Moshiri for going with Ancelotti and at the end of the day, it's Ancelotti.
We got 59 points in his one full season, blurred of course by lockdown, but that run-in drop down the league was dreadful. Everton gambled on getting Europe and without that the fees and wages they spent in 2020 came home to roost. Again, had the club managed to get the forward in they wanted in January 2021, it was probably a different story, but Brands didn't act fast enough - they wanted Hwang, who I think Carlo would probably have liked as a back-up option. He obviously didn't rate King at all.
But it's that 2021 summer where it really unfolded. Carlo leaving of course hit hard but they got compensation. They had deals lined up - Livramento was through the door, literally like ready to sign - before Benitez said no. They had money to put towards Dumfries, it wouldn't have been easy but they would have made it work, but Benitez said no. Inter had the money and got the deal done quickly.
They had other striker targets - a lad in Belgium (Openda I think) and a Portuguese player, both younger, around 22-23. Benitez wanted Rondon. And that Rondon deal wasn't cheap at all because the player himself bought out the rest of his contract in China.
Benitez was given total remit over transfers, everything. Moshiri backed him to the hilt. Until even he then started medalling.
So it's a long and winding road, as Paul once sang.
2017 and 2019 played their parts, but 2021 was the killer. Moyes was there in 2021, he'd have taken it, he was out of contract and delayed signing on at West Ham because he wanted the Everton job. Moshiri went with Benitez.
