Some the media stuff he’s done lately sounds like he’s (comparatively) skint, one of his stories was he lent £250k to a financial adviser who was struggling a bit, he acknowledges he perhaps should have seen that as a bit of a red flag!I disagree with you a little on him but agree with the timing . I’d also imagine it’s possible he’s struggling to find a management gig so is perhaps reinventing himself as a pundit .
Also talks about how he was declared bankrupt previously and had to pawn his wife’s engagement ring.
On that Peter Crouch podcast his last Everton salary was £12k per week which I found unbelievable, but perhaps explains his raised media profile and autobiography