Kavanaugh is probably the most controversial among the top three picks, as he makes both conservatives and liberals uneasy. Liberals would be uncomfortable with his work for Independent Counsel Ken Starr and the George W. Bush administration, while conservatives worry about his ruling that they believe laid the intellectual foundation for John Roberts’ decision to uphold Obamacare.
The latter concern, at least, is misplaced, as Kavanaugh was ruling on mootness, a separate claim unrelated to the overall merits of the Obamacare claim. Nevertheless, his ties to Bush and Starr would probably cause Democrats to launch a full tilt campaign against him similar to the one that would be launched against Barrett, without exciting conservatives to the same degree that Barrett would.
So why would conservatives want him? The answer is simple: Since Scalia’s death, conservatives have been without a William Brennan. What on Earth does that mean? Courts are usually divided into eras by chief justices (the Burger Court, the Rehnquist Court), but the chief is rarely the leading intellectual on the court. The chief justice is charged with a bevy of administrative tasks and institutional responsibilities.