The worst item combination is the Red Shell and the Blue Winged Shell. For the Red Shell, hold a Banana, Green Shell, or another Red Shell behind you. It will break. For the Blue Winged Shell, use the "Avoid Blue Shells" glitch to avoid it. If you cannot and are unfortunately in first place, then expect to lose a lot of places. Alternately, break the Red Shell, let the person in second place get close to you, and you will be blown up together. You will still lose places, but if it is DK or Bowser, then you will want to.