This essay speculates on what an Obama judiciary might look like and how the selection process is likely to play out. This is presented against the backdrop of past experience. First, the essay traces the demographic diversification of the federal bench from the presidencies of Franklin Roosevelt through George W. Bush. Second, this essay considers ideological diversity and presents voting data from the first three completed terms of the Roberts Court. Third, the essay considers the selection process, including confirmation of lower-court judges by the Senate. It concludes that President Obama can be expected to promote further gender, race, and ethnic diversification as well as to seek to moderate the current ideological imbalance on the courts. He will likely keep the existing institutional apparatus of judicial selection and will restore the American Bar Association to the role it had prior to George W. Bush’s presidency. Confirmation may well prove to be a challenge in a Senate that is not filibuster-proof.