Lessig knows both Diane Wood and Elena Kagan well, having been friends with both of them for over 20 years. Though he has high praise for Diane Wood, he says Kagan is not only a progressive but she also possesses a quality not found in others on the short list:
I believe there's an aspect to Kagan's experience that sets her apart from others on the short list. Kagan has had practical strategic experience. Her most important work over the past two decades has been in contexts where she has had to move people to see things as she did. And through that experience, she has developed a sixth sense for the strategy of an argument.
She matches that insight with a toughness that can get what she wants done. That doesn't mean triangulating. It doesn't mean "compromise." It means finding a way to move others to the answer you believe is right.
This is the single feature the liberal side of this conservative court lacks most. Even Justice Stevens was too quick to run off to a corner to write his universally brilliant dissents from insane majorities. Breyer too too often seems content in his law professor way to write an opinion that sounds good when read aloud to himself, but in light of the evolving jurisprudence of the Court, is tone deaf to the view of others. Too many of our progressive colleagues swing for the bleachers of history, rather than victories now. Too many are content with simply knowing that their liberal law professor friends are busy praising their opinions in constitutional law classes rather than fighting to find a way to split the ideologues on the right with their own principles and rhetoric.Again, I'm not talking about triangulating. The point is not that we need someone who knows how best to compromise. The point instead is that
we need a justice with the energy and strength to use the legal materials provided by the other side to advance the right answer... In a line: She marries the brilliance and strength of the very best Justices, a practical skill not of compromise but argument, and deep experience inside the executive branch. It is a broad base of experience, producing an understanding of what is possible, and skill to produce what is right. http://www.huffingtonpost.com/lawrence-lessig/a-case-for-kagan_b_551511.html Lessig's lengthy and erudite piece is worth reading in full. For example, he addresses many of the "concerns" some have in a legally-informed manner.