John Roberts, Chief Conservative Strategist

For those who follow the Supreme Court, psychoanalyzing Chief Justice John Roberts is irresistible. His mild manner and measured tone baffle observers who expect bombast from conservative jurists. He refrains from Antonin Scalia’s rhetorical theatrics and Clarence Thomas’s enthusiasm for overturning precedent. He most notably shied away from a potentially explosive political confrontation in June 2012, casting the decisive vote to uphold the Affordable Care Act. That earned Roberts a barrage of invective from conservatives. In a pair of cases a year later, he whipsawed liberals who’d fantasized about a rift on the court’s right by curbing voting rights and affirmative action. His latest majority opinion, in a 5-4 decision announced on April 2 that ended decades-old restrictions on campaign contributions, provides fresh fodder for scrutiny. It also hints at the plans of a chief justice who, at 59, could remain in his powerful post for 20 years or longer.

In the April 2 decision, Roberts argued that Watergate-era limits on how much money individuals can spread around each election year, intended to thwart corruption, interfered with free speech. “Money in politics may at times seem repugnant to some,” he wrote, “but so, too, does much of what the First Amendment vigorously protects. If the First Amendment protects flag burning, funeral protests, and Nazi parades—despite the profound offense such spectacles cause—it surely protects political campaign speech despite popular opposition.” With that concise declaration, Roberts diminished the federal government’s power and increased wealthy individuals’ influence over elections. Within hours of the ruling, fundraisers were on the phones hitting up previously maxed-out donors for more cash.