Quoted By:
Fast flying and steel types, symbolising the airforce/army. No water types, since his navy sucked unless there's some good submarineish Pokémon. I could also see some fire/electric types.
I'd go for:
Scizor
Metagross
Chatot (For his charisma/speaking ability)
Houndoom (He loved his dog)
Aerodactyl
For the last slot:
Magmortar (Artillery)
Victini (Wunderwaffe)
Braviary (German Eagle)
Sharpedo (Submarine)