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[Moggy Cattermole]

Should they not have been more worried about problems closer to home..?

[HundertzehnGustav]

well you know the italians... always good for a publicity stunt.

Reputation is important...

[agracier]

Should they not have been more worried about problems closer to home..?

Sure they should have, but that's how things go in wartime and especially in wartime with dictators. They get a propaganda bee in their bonnet, get fixated on looking good, or looking strong and then tend to ignore more pressing concerns.

But just because Mussolini didn't do well in the end doesn't mean that propaganda and moral lifting isn't an important part of war. The Doolittle Raid on Tokyo in 1942 is a point in case, not very unsimilar to a never realized New York bombing ... as a raid judged on destruction of enemy war production means it didn't accomplish much at all. But by bombing Tokyo it inspired the US to look at things in a positive light. It was wonderful for national morale. The Doolittle Raid on Tokyo was just as much a publicity stunt as anything else ... the Italian raid though is that it was never carried out and even worse, Mussolini did not win the war.

The same would have happened with an Italian bombing of New York. Imagine the headlines around the world. Imagine the scope for movie productions ...

[Kopfdorfer]

....or IL2 modders 

map of New York including Statue of Liberty , Staten Island , Coney Island , Empire State Building and Yankee Stadium

Piaggio P108 Bomber

Type XIV Milk Cow Uboats

US Destroyer Escorts

Ventura Bombers

Junkers 290

A proper sea going tugboat (Foundation Franklin)

etc , etc

Kopfdorfer

[Pursuivant]

Actually, a propaganda raid against a U.S. city might have had strategic advantages. It's quite likely the U.S. would have panicked and diverted lots of resources to defend the U.S. mainland against further attacks.

A good example was the British reaction to German bombing raids during WW1 - lots of British fighter squadrons kept at home, to shore up civilian morale, which could have been used better elsewhere. To some extent, the Doolittle Raid had the same effect on Japan (http://en.wikipedia.org/wiki/Doolittle_Raid).