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Over at Liberty & Power, historian Paul Moreno, author of the superb Black Americans and Organized Labor, has a long and fascinating post looking at the problems with several previous empathy-driven Supreme Court nominations. As Moreno notes, President Theodore Roosevelt told his friend and ally Sen. Henry Cabot Lodge that it was "eminently desirable that our Supreme Court should show in unmistakable fashion their entire sympathy with all proper effort to secure the most favorable possible consideration for the men who most need that consideration." To that end, Roosevelt appointed progressive hero Oliver Wendell Holmes to the Court in 1902. Here's Moreno on how that worked out:

Roosevelt particularly liked Holmes' opinions in labor cases, for he expressed more sympathy for labor unions than most judges of his day. But TR was mostly interested in Holmes' views on the emerging American empire. Shortly after the Spanish-American War, President Theodore Roosevelt was concerned that the Supreme Court might insist that all constitutional guarantees extended to our newly-acquired empire-in popular parlance, that "the Constitution follows the flag." In 1902, TR sought and obtained a pledge from Holmes that he would not apply this standard. Holmes then lied to the press about his secret meeting with the President. He dutifully voted with the majority in the so-called Insular Cases, which held, for example that the right to a jury trial did not extend to Filipinos or Hawaiian....

For most of his career, Holmes really didn't believe that there were any constitutional limits at all to government power. He advocated the complete separation of law and morality, writing, "I often doubt whether it would not be a gain if every word of moral significance could be banished from the law altogether," he wrote, "and other words adopted which should convey legal ideas uncolored by anything outside the law." He continued, "Manifestly... nothing but confusion of thought can result from assuming that the rights of man in a moral sense are equally rights in the sense of the Constitution and the law." Essentially, he thought that the majority had the power to impose its will on the minority, for good or ill. In 1873 he wrote that "It is no sufficient condemnation of legislation that it favors one class at the expense of another, for much or all legislation does that.... Legislation is necessarily a means by which a body, having the power, puts burdens which are disagreeable to them on the shoulders of somebody else." Holmes himself confessed in 1919 that he had come "devilish near to believing that ‘might makes right.'"

Much more here.