> Saddling Uber with a 100 billion dollar tax bill will get them a bankruptcy proceeding and $0.
OTOH, it will also discourage future violations of the same kind, because people don't generally start businesses to lose the time and resources poured into it just for the joy of denying the IRS taxes. So, even though it may not be optimal on a narrow view, it may be desirable on a longer view. Corporate tax evasion is motivated by profit, and as long as it is more profitable to break the law and make a partial settlement later, businesses will be encouraged to do it. It if it is catastrophically not profitable to do that, the incentives are different.
OTOH, it will also discourage future violations of the same kind, because people don't generally start businesses to lose the time and resources poured into it just for the joy of denying the IRS taxes. So, even though it may not be optimal on a narrow view, it may be desirable on a longer view. Corporate tax evasion is motivated by profit, and as long as it is more profitable to break the law and make a partial settlement later, businesses will be encouraged to do it. It if it is catastrophically not profitable to do that, the incentives are different.