This is not a matter open to fair-minded dispute, never mind partisan disagreement. Even the president and Secretary of Health and Human Services Kathleen Sebelius agree that the rollout of Obamacare has been a "debacle" (Sebelius' word). Revelations in the press and in congressional hearings show that the administration was warned prior to both the shutdown and the Obamacare debut that Healthcare.gov was as ready to go live as a kid's make-believe refrigerator-box submarine was ready to explore the ocean depths.
If Obama were a chess master -- or even a fairly adept checkers novice -- he would have known that when you're not ready to do something incredibly important, it's best to buy time. He could have traded a delay (Three months? Six months?) for some major budget concessions, maybe even lifting the sequester. Perhaps his base wouldn't have liked it, but he could have easily spun the compromise as a necessity given how irrational and "extreme" the GOP was being.
Publicly he'd say he was paying a ransom to "kidnappers" and "hostage takers." He'd denounce Republicans for delaying precious insurance coverage for sick kids and frail oldsters just to score partisan and ideological points.
But privately, ah privately, the master strategist would be stroking his proverbial white cat -- or, in reality, his hypoallergenic black dog -- while breathing a sigh of relief that he bought himself some time to fix his woefully mangled healthcare reform.
Obviously he wouldn't want to delay Obamacare. But that decision was out of his hands due to his administration's incompetence. The only choice before him was whether he would get the blame for the delay or if the Republicans would.
Why Obama didn't do this and why it didn't occur to him are good questions. Hubris obviously played a role, as it does in nearly everything this White House does. But the best answer is he didn't know how terrible things were over at HHS. In other words, the chess master didn't even know what pieces he had on the board, which is usually not something we associate with chess masters. It's something we associate with people who don't even know how to play the game.