As we have become well accustomed to during his first year as President, Barack Obama does not live for political street brawls in the capitol. He broached health care reform last summer with an initial hands-off approach, hoping that the best spirits of bipartisanship would foster legislative success. Last week, his administration preempted any forthcoming cap and trade legislation by lifting the federal restrictions on offshore drilling. The announcement left progressives feeling a bit April-fooled and wondering what the President saw in “Drill Baby, Drill!” The slogan seemed to have been chosen more because Sarah Palin could remember it without having to write it on her hand rather than its potential to actually solve the nation’s energy problems. And now with the resignation of the venerable Justice John Paul Stevens, we are once again left wondering the same question. Will Obama attempt the impossible task of finding and nominating one who can fill Stevens’ Shaq-sized shoes as the conscience of the court’s liberal wing, or will he try to garner Republican support by nominating a moderate at the expense of shifting the court to the right?

Stevens’ ability to counterweight the court’s most draconian conservatives and to persuade Justice Anthony Kennedy to join with the court’s liberals characterized his long and storied career. He has been the leader of the liberal wing, taking charge in upholding civil liberties, such as the right to Habeas Corpus in Rasul v. Bush. He also penned impassioned, powerful dissents in cases like Heller v. D.C. and Citizens United v. FEC, when the court’s conservatives have dispelled the myth that somehow they do not engage in judicial activism in striking down longstanding laws.

Since the nomination of Byron White, incoming justices have been more conservative than the ones they have replaced, and given Obama’s short list, there seems to be little hope that the court will not shift even further to the right with Stevens’ successor. Yet, here’s to hoping that the administration will shift from its previous approach to become a party that, in the open words of Rush Limbaugh, not only “hope[s] he fails,” but has done everything in its power to make his failure a reality and not a mere hope. This includes filibustering judicial nominations that Republicans ultimately like, as evidenced by their bipartisan support in committee.

If there is one conservative to whom Obama should listen to though, it is Alberto Gonzalez, Attorney General under Bush. Three and a half years ago, he said, “Few presidential decisions are more important than lifetime appointments to the federal bench. Many of a president’s policies and programs … can be undone … but a judicial appointment lasts a lifetime.” A less than perfect health care bill, energy policy and potentially cap and trade bill can all be changed and amended. A Supreme Court Justice can shape and influence the character of the law for the next 30 years.

Beyond that though, the only place Obama should consider bipartisanship with regard to his nominee is that nominee’s ability to persuade other justices — especially Kennedy — in the same manner as Stevens did. Even if political expediency plays more of a factor in Obama’s decision than legacy, it still does not preclude the nomination of a liberal heavyweight to Stevens’ seat. The President should play with the public’s perception of his nominees by interviewing and vetting some of the most liberal candidates, such as Kathleen Sullivan and Harold Koh, leaving him free to pick someone like Diane Wood and have her seem relatively moderate in comparison. The Republicans are likely to oppose anyone nominated unless that person is one who would dramatically alter the ideological composition of the court. There exists no evidence from the past year that they will at all be reasonable and fair.

Barack Obama will conceivably have one more appointment to make in the remainder of his first term — Ruth Bader-Ginsberg, given her ill health. At that point, he will have replaced three-fourths of the court’s liberals. Beyond that, even given the age of Antonin Scalia, the court’s oldest conservative, there are no guarantees that he will have the chance to fill a fourth seat should he win a second term as President. If he does not assiduously guard a conception of the Constitution as a living, progressive document, then we will end up with the rigid, detached court whose inability to see the consequences of their decisions will lead to more flawed outcomes like Citizens United. This is a decision that will far outlast his presidency. The overarching principle by which Obama should choose his next justice is whether that person will spend the next several decades shaping an America of which he can truly be proud.