1.
Infinite money glitches don't last. ESPN's ability to raise prices at will bred overspending that became fatal when subscriber decline hit.
2.
Middlemen get disintermediated. When both suppliers (leagues) and distributors (streaming) can go direct, your bundling power evaporates fast.
3.
Build cash reserves in good times. Spending like there's no tomorrow in the 2000s left ESPN with no cushion when the market shifted hard.