Is Kimbo's permit gauranteed

Is Kimbo's work permit guaranteed to be granted

Also his nickname should be "Legs"

No. As I understand it he doesn't meet the basic criteria for automatic acceptance . But pesumably the club must have made some enquiries about the likelihood of getting one before they signed him. Hope so.

I didn't think he automatically qualified either

I think that a player has to have played 75% of his country's competitive internationals in the previous 2 years. Don't think Kimbo has. ( Don't think the Olympics count but absences through injury can be taken into account) There is provision, if the number of matches criterion is not met, for the application to go to a Panel of Experts who can grant a permit if they are convinced that the player is of very high quality and will add to the game in this country.