“Chief Justice John Roberts initially sided with the Supreme Court’s four conservative justices to strike down the heart of President Obama’s health care reform law, the Affordable Care Act, but later changed his position and formed an alliance with liberals to uphold the bulk of the law, according to two sources with specific knowledge of the deliberations.
Roberts then withstood a month-long, desperate campaign to bring him back to his original position, the sources said. Ironically, Justice Anthony Kennedy - believed by many conservatives to be the justice most likely to defect and vote for the law - led the effort to try to bring Roberts back to the fold.”
— Jonathan Cohn, “Did Roberts Change His Vote?”
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“Chief Justice John Roberts initially sided with the Supreme Court’s four conservative justices to strike down the heart of President Obama’s health care reform law, the Affordable Care Act, but later changed his position and formed an alliance with liberals to uphold the bulk of the law, according to two sources with specific knowledge of the deliberations.

Roberts then withstood a month-long, desperate campaign to bring him back to his original position, the sources said. Ironically, Justice Anthony Kennedy - believed by many conservatives to be the justice most likely to defect and vote for the law - led the effort to try to bring Roberts back to the fold.”

— Jonathan Cohn, “Did Roberts Change His Vote?

What does it mean to be a successful Chief Justice?

“As Roberts recognized, faith in the neutrality of the law and the impartiality of judges is a fragile thing. When I teach constitutional law, I begin by telling students that they can’t assume that it’s all politics. To do so misses everything that is constraining and meaningful and inspiring about the Constitution as a framework for government. There will be many polarizing decisions from the Roberts Court in the future, and John Roberts will be on the conservative side of many of them. But with his canny performance in the health care case, Roberts has given the country a memorable example of what it means to be a successful Chief Justice.”

-Jeffrey Rosen,”Welcome to the Roberts Court: How the Chief Justice Used Obamacare to Reveal His True Identity