> This isn't arbitrage, it's looking for loopholes.

"Have someone who pays the lower amount do the thing" is precisely arbitrage.

> That would level out in their feasting years, after all (assuming you're using the previous year's taxable income, or an average income over the previous three years or so).

Their income for the last three years was $10k, $10k and $1M. Their 20 year average is $80k but the three year average is $340k. So now you're increasing their exposure even more -- before they get a hugely disproportionate fine if it happens to be in the one year they made $1M. Now they still get a disproportionate fine but are exposed to it for three times as long.

> The chauffeur is subject to the rules around their CDL or similar, or is in service of their employer. When driving a work vehicle, my fines are already directed at my employer.

Michael Dell hails a cab and then the driver gets a speeding ticket. No evidence driver had any idea of his passenger's net worth; no evidence the passenger ever requested exceeding the speed limit and couldn't see the speedometer from the back seat. Is this a billion dollar fine? Who pays it, the person who has nothing like a billion dollars or the person who did nothing wrong?

It's clearly unreasonable to impose the fine in that case, but it's also easy to use it for arbitrage if you don't.

> It blows my mind how much we are willing to bend over backwards to ensure the powerful won't suffer a moment's inconvenience in this country.

Maybe we should have a preference for rules that are effective rather than performative.