Even those who disagree with Supreme Court chief justice John Roberts on the issues usually can’t find fault with his intelligence and skill as legal mind, says Joan Biskupic, legal analyst and author of a biography about Roberts. Roberts quickly rose to prominence through Harvard Law School and the Reagan administration, cementing his reputation. But Biskupic explains how it was one of his few failures that helped him reach the Supreme Court:

There are two competing impulses that drive John Roberts’ judicial decisions, says Joan Biskupic. One side of John Roberts is idealistically conservative — he did, after all, cut his teeth working for the Reagan administration. Another side of Roberts, though, believes vehemently in protecting the legitimacy of the Supreme Court. And in Roberts’ view, contentious decisions about polarizing issues damage the legitimacy of the Supreme Court in the public eye. 

Biskupic says that because these impulses are often competing, Roberts has to balance his personal ideology with the realities presented to him on a literal case-by-case basis. And despite his best intentions, he often ends up confounding outside observers with decisions that sometimes fail both his ideology and his concerns for the court. 

Likeability might seem like a superficial trait for such an esteemed institution, but the quality of personal relationships between Supreme Court justices can have very real implications for how decisions are reached. Joan Biskupic says that John Roberts’ inexperience and ideological inconsistency have sown confusion and distrust amongst his fellow justices: 

It’s clear that chief justice John Roberts trusts himself above all to make momentous decisions, but how does he actually reach those decisions? In response to an audience question about how to characterize John Roberts’ decision making style, Joan Biskupic breaks down how her analysis: