I think there’s an interesting counterfactual in what happens if Chelsea win the penalty shootout in the '08 Champions League final. Like a few people have said, Grant’s record at Chelsea was pretty excellent that season, even if he did have a strong platform left by Jose Mourinho to build on. Ultimately, Grant wasn’t very charismatic and had little reputation as a coach outside of Israel to fall back on, so he was always going to be judged harshly at Chelsea. What really did for him was back to back relegations in 2010/2011 - Portsmouth he actually left with his reputation enhanced because he conducted himself with a lot of dignity at a club in absolute meltdown, and steered them to the FA Cup Final, but his West Ham team were absolutely dreadful. Since then he’s bounced around the world and obviously had a more than respectable career, but he’s probably never going to be anywhere close to one of Europe’s big five leagues again.