Why might a company with positive EBITDA for 10 straight years still go bankrupt?

Answer

Several reasons: (1) CapEx-heavy business — EBITDA ignores CapEx, so a capital-intensive company can show positive EBITDA but generate negative free cash flow; (2) Crushing interest expense — EBITDA is pre-interest, so heavy debt loads can wipe out cash flow; (3) Debt maturity wall — if all debt comes due at once and refinancing markets are closed, the company runs out of money; (4) Large one-time charges (litigation, settlements, fraud) sitting outside of EBITDA; (5) Negative working capital swings that drain cash.