Ooooh, nice one! What all of that means is a mystery, but it's full of clues.
Any older US military people might know some of the insignia better than me and my Googling, but this is my 2 cents:
The eagle looks just like the insignia for the rank of Colonel in the US Army or Army AirForce...except the olive branches and arrows are replaced with a banner, where we wish a name was engraved.
The fouled anchor I always thought represented the US Navy, but I guess it can be more specific than that. Yours has the added crossed flag and spear(I think). No clue or Googly results for that.
The symbol on the left is interesting. I know the castle represents the Army Corps of Engineering. The crossed cannon, sword and rifle are parts of a similar Master Gunner insignia, but that also has a missile. Your cig case's insignia all tell a story of rank and experience, and it is quite elaborate and well made.
Either Colonel what's-his-name lost this meaningful personal item before he got it engraved, or it's just a bunch of military symbols used to decorate a carnival prize.