There's been a lot of speculation, both in the media and in the comments of this blog, in recent weeks over whether or not Di Matteo has done enough to convince Roman to keep him on as the next permanent Chelsea manager. I'm of the opinion that if you were to rank all of the managers in the world in some form of league table, Bobby wouldn't be at the top of the league. Therefore, if one of the guys above him on the leaderboard was available then we should thank Roberto for all that he has done and wish him well on his future endeavours.
I do, however, think that the relatively small number of managers better than him (and the general stability of those guys in the jobs that they currently have) will mean that we would struggle to persuade one of them that a move to West London is of a good idea and in this situation, offering the job to Di Matteo is the right decision.
This brings me on to my major point here. Throughout all of the coverage of whether Di Matteo has 'done enough' or 'earned the right to stay', I've yet to see anybody question whether he would actually want to, or whether he would turn the position down if it was offered.
Di Matteo took the assistant manager job at Chelsea as a club legend. The unpopular Villas-Boas was given his marching orders, after a pretty unsuccessful tenure by any measurement, and Bobby took up the unenviable task of trying to salvage the season. Not only did he pull off some pretty miraculous wins against Napoli and Barcelona, but he also collected another FA Cup to add to the trophy cabinet. A feat that nobody would ever have imagined back in February with the performances that the team were producing. And then, to top it all off, he brought home the holy grail. He somehow managed to lead this wayward team to the Champions League final and came out victorious.
That last paragraph was mostly for my benefit (it was pretty fun to write) because I'm fairly sure anybody reading this already knows what happened. The point is, though, where can he go from here? He's set himself a very high bar; the only way to improve on this season would be to win The Treble, a feat which has only ever been achieved once by an English club (no, the Liverpool ones don't count) and something that this team is unlikely to accomplish in the near future.
Di Matteo was a legend before. Now he's an absolute hero. And the only way from this point is down. He's a smart man and I could see him taking the opportunity to go out on a high. He might well decide to try his luck with one of the many other job offers he's likely to get following his achievements this season rather than suffer the ignominy of being sacked when he inevitably fails to live up to his own high standards.
Whether or not you believe Bobby is the man to lead Chelsea into the future, there's a very good case to be made that it's in his best interests to walk away.