The Battle for Monte Cassino began on the 4th of January 1944, and was essentially a series of battles along the German Gustav Line. Smack in the middle was the Benedictine Monastery at Cassino.
Apparently, the Germans were acutely aware of the historical significance of the Benedictine Monastery at Cassino, and Field Marshall Albert Kesselring, ordered German units not to include the monastery itself in German defensive positions. Accordingly he informed the Allies of his actions.
Of course, no one knows exactly how well the Germans adhered to this order, and with the Monastery being a hugely tactical advantage for it’s all encompassing views of the Allied positions, the Americans decided to bomb the crap out of it.
On February 15th, American B-17 and B36 bomber laid waste to the historical site and two days later, German Paratroopers poured into the ruins to defend the area.
Once these German Paratroopers took position, the Allies attacked four times before routing them with a loss of 54,000 Allied men to the German loss of only 20,000.
No one knows if the bombing of the Monastery ultimately helped or hindered the Allied advance through Italy.
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