there could be 1,000 escapes, where each one was enabled by novel and unexpected chain of 0-day exploits. not likely to be considered reckless disregard in court.
there could be 1 escape, where there was no sandbox, no guardrails, no instructions to avoid damage, etc. which would likely to be considered reckless disregard (well, more likely to be, but still, reckless disregard is a high bar).
reckless disregard is a specific legal term, with specific criteria, and none of the criteria cares about "number of attempts" (or number of escapes, etc.).