07/01/2012 12:31 pm ET Updated Jul 01, 2012

Keith Olbermann: Obamacare Ruling Gives Mitt Romney 'Two Insurmountable Problems' (VIDEO)

Keith Olbermann believes that the Supreme Court's recent health care ruling leaves Mitt Romney with not one, but two "insurmountable problems."

He was speaking on ABC News "This Week" on Sunday. The court's decision to uphold the individual mandate dominated the roundtable discussion. After declaring the outcome a "victory" for Obama, Olbermann said that the outcome was only bad news for Romney.

He argued that Romney's first problem was that he was running against a program very similar to his own signature health care legislation in Massachusetts. The second, he said, was that the candidate now has to go against Chief Justice Roberts.

Olbermann explained that Romney "also has to say he's opposed to the decision of somebody who was until this week perceived as a supremely conservative chief justice... That can't be a win for him. He's got two now insurmountable or newly insurmountable problems when he only had one when the week began."

Contributor George Will disagreed. He argued that the decision actually helped Romney because the mandate will be upheld as a tax, which people will not want.

Donna Brazile objected to his line of logic, nodding to Olbermann's argument. "Obamacare is Romneycare at a federal level," she insisted.

Later, Olbermann referenced his own experience spending time in the hospital with his dad. "Anything that moves the ball towards this primary role of our government, protecting its citizens, will be viewed... as a positive thing," he said. "And those who stand against it will probably suffer, if not in the short term then in the long term."

Watch his remarks beginning at the 10:16 mark in the clip above.