Limitation of Insurance Liability

I'm new to insurance liability and have only found research related to medical risk of exposure. I have data for 30 events that list the type of event, the probability of it occurring and the liability in dollars to the contractor if it does occur. If we now set the liability limit at say $20,000, I need to calculate the odds that an event will occur that would be in excess of it. Could someone please get me started? Is it some sort of cumulative calculation?

Just a thought, but could it be as simple as a Monte carlo simulation where events are activated by a random variable?
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