Prior studies hypothesize that judges time their retirements to allow a like-minded president to select their replacements. We propose a modification to this argument and theorize that during the earlier part of a district court judge’s career, it is the likelihood of elevation to an appeals court and other career-oriented concerns that affect whether the judge resigns or stays on the bench. It is during the latter stage of a judge’s career when the desire to be replaced with a like-minded judge affects the retirement decision. Our analysis reveals that judges who are not yet pension eligible are influenced by being passed over for appeals court nominations as well as financial incentives to leave for private practice. Only judges who have attained pension eligibility appear to consider their ideological compatibility with the president when deciding to call it quits.