Howard Fineman tells us what went wrong, other than the predictable perfidy of Evil Republicans and their big business paymasters:

Murky campaign promises
...The president is for “reform,” which says… nothing.

Orszag’s fantasy
Every president wants to reconcile frugality and generosity, and there is always an ambitious and clever aide willing to tell him it can be done. In Obama’s White House it is Budget Director Peter Orszag, who confidently told Obama that carefully administered universal health coverage would save the government money in the long run.

...Focusing on the have-nots
...the White House all along should have been focusing on the fears of the 85 percent who have insurance, not on the 15 percent who do not.

Jonah Goldberg has his view - "if you actually wanted Obama-care to pass, casting a majority of Americans as being stooges of racist goons may not be the best way to go."

He left out greedy and stupid.