Did he intend to? Or was it obvious that driving a tractor down the flooded street would cause additional damage.
Obviously he can't see what his wheels are going over, so there may have been bins, planters, etc. that were damaged.
For there to be criminal damage, the first requirement is damage to property. If the property is already damaged and the additional damage you do makes no change to the value of the repair/replacement etc. There is no damage.