I have been wondering the same thing myself. IMO his personality is much more dominant than Charlie Jacobs' or Don Sweeney's for that matter.
As for "taking the keys away" from Charlie- I don't think this is realistic. Jeremy Jacobs is in his 80s, he's stepping away from running his companies and frankly there isn't time for him to see if any of his grandchildren might be capable of taking over the hockey team if they want to keep it in the family.
Papa Jacobs turns 77 in a few days and seems to be in good health.
Delaware North overall has been struggling the past few years and lost a major contract with the US Government and have lost contracts with a few venues to a Chicago based company Levy that is partially owned by the Wirtz family.
http://www.levyrestaurants.com/venues/
DN has always considered Boston a separate division of the family business and now they have finally decided to develop around North Station. The Bruins themselves are owned directly by Jeremy and his wife and TD Garden is owned by Delaware North.
DN is 100% owned by the family but the concession business is becoming more competitive.
Those of us who go to the games regularly have notice that the in-game presentation (not counting the game itself) has declined in the past few years. The Bruins have never been known to be fan friendly with customer service and promotions and I thought that would get better under Charlie but it has gotten worse.
On a personal note my family has had season tickets since 1948 and while they are in my name my nephew uses the tickets but he is at the end of his rope. He lives on the Cape and he doesn't want to deal with downtown anymore.
Something drastic needs to be done now to keep the entire business relevant.