but is it really any worse than the guy who filed for bankruptcy FOUR TIMES?

This is you not understanding how business and basic economics works. When you are a billionaire who has owned thousands of companies, letting loose of certain companies to protect the empire is normal practice.

https://en.m.wikipedia.org/wiki/Strategic bankruptcy

A strategic bankruptcy may occur when an otherwise solvent company makes use of the bankruptcy laws for some specific business purpose.[1] A strategic bankruptcy can be used to get away from expensive contracts otherwise unbreakable. For example the airlines Sabena and Swissair have gone bankrupt and been restructured and got away from high salary and expensive pension contracts with pilots and other staff. In 2002 Kmart filed Chapter 11 for protection from creditors. One of the main problems affecting Kmart's cash flow and therefore its liquidity was that Kmart was locked into long-term leases at premium rates with respect to various unprofitable stores. While in chapter 11 reorganization, Kmart was able to renegotiate or rescind those particular leases.

In some countries, like Sweden, it is common at least for smaller companies with deep debts, to have a bankruptcy, and close down the company, but where the owner has prepared a new company which buys important assets including the name, and continues with much smaller debts.