Rocky V (1990) Rocky goes broke.

After returning home, it is discovered that Paulie unknowingly had Rocky sign a “power of attorney“ over to Rocky’s accountant, who had squandered all of his money on real estate deals gone sour; in addition, the accountant had failed to pay Rocky’s taxes over the previous six years, and his mansion had been mortgaged by $400,000. His lawyer confirms this, but tells Rocky that it is fixable with a few more fights. Unwilling to go bankrupt, Rocky decides to accept the mega fight with Cane. After seeing a doctor, however, he is diagnosed with permanent brain damage. Adrian convinces him to retire, which he reluctantly accepts.