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1271
If the parked car had closed off the street in a manner that cars could not get by, people would have had the right to move the car even at the risk of damaging it (Shulchan Aruch, CM 412:2) based on the rule that one can take the law into his own hands. However, here it was possible to pass carefully.
First we must determine what category of damage was done. Was it damage that a person did himself because the driver held the steering wheel and pressed on the gas, or was it the damage of his property? In the similar case of one riding his horse and damaging, the Rosh (101:5) says it was considered damage done directly by the rider. Regarding such damage, the mishna (Bava Kama 26b) says that the damager is liable even if there were extenuating circumstances, but Tosafot says that this is only if the circumstances were somewhat under his control to prevent. If, though, he had the chance to avoid the damage only to the degree that one can prevent robbery, he is exempt. The Ramban, though, says that the damager is liable no matter the level of extenuating circumstances, and the reason the Yerushalmi says that he is exempt if the damaged put the object near the sleeping damager is that the damaged was at fault.
In our case, according to Tosafot, the damager should be liable because it was negligence not to slow down when he saw the road had narrowed. The question is, according to the Ramban, whether this case is equivalent to that of the objects placed next to the sleeping person. The mishna (Bava Kama 27a) says that when one puts a barrel in the public domain and it is damaged by someone who trips over it, he is exempt. The gemara asks that he should be obligated because he should have looked where he was walking and answers that is not normal for people to be so careful when walking on the path. The Ramban will have to explain that one who puts his barrel in a place where people are not careful about it is considered one who caused the damage to his own object. However, in our case, since one can easily see the parked car, the Ramban should agree that the driver is liable.

P'ninat Mishpat (762)
Various Rabbis
99 - The Proper Level of Shemira
100 - Damage to an Illegally Parked Car
101 - Laws of Shomrim Watchmen
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