No. The whole point is that these "risky behaviors" are quite capable of inflicting damages (such as the permanent contamination of water tables in certain areas) that can't possibly be compensated by the any conceivable "insurance payout". Such behaviors (once identified) should be strictly prohibited. Economic penalties against the corporate entities (aka "regulation") will of course never be sufficient. The only effective deterrent is jail time for for the decision makers (in addition to complete confiscation of their personal assets).
And BTW by "jail time" I mean serious jail time, as in multiple decades of jail time, and/or life sentences if necessary.
Flipping back in the chronology of your post a bit:
We lurch between economically damaging regulations after something really bad happens, to regulatory capture after industry lobbying gets the attention of politicians.
I agree with you wholeheartedly about the need to stop lurching. That's why we need to get serious about criminal penalties for this kind of behavior -- not to throw in the towel and entrust the safety of our irreplaceable freshwater resources wondrous self-regulating powers of the insurance industry.
The environment is not a casino, in other words. This is the health of uncounted generations we're talking about -- which will come into being long after any of these massive insurance payouts your proposal would seem to bank on could have possibly had any ameliorative effect.