It feels a bit like he’s done all he can here. Give yourself a 5 year timespan, is it easier to take Arsenal “forward” in those 5 years, or Milan? I think to take Milan from a bit of a mess to not a mess is an easier task, and with a little investment I imagine in the longer term it’ll be easier to make an Italian club successful over an English one.
To take Arsenal forward from here feels like a big task. Our biggest hopes for a consistent CL place are declines in clubs like Spurs or Chelsea but no matter what we do we’re always likely to be a step behind the likes of City and United.
Fom a personal point of view too it’ll be easier for him in the future to be the guy who was relatively successful as a CEO of two big clubs rather than just one where it may look like he had a pretty comfy ride.
It also sounds like he may have been undermined by the ownership regarding the Wenger situation last year and if that’s true then we don’t know how many other disagreements there have been over things.
Where Milan is now owned by a fund, maybe he’ll actually get full control of those sorts of decisions. I imagine they want him to bring self-sustaining growth to the club and if he can pull that off then he’ll be deserving of credit. If I was him, I think I’d take the opportunity to move on to another good job after a decade in the same one.