That’s the subhed of my new Confirmation Tales post, titled “Teddy Roosevelt Quickly Regrets Appointing Justice Holmes.” In Roosevelt’s distinctively vivid and outsized way, he provides an enduring lesson in how presidents are disposed to misjudge Supreme Court candidates.

In the course of my post, I discuss a remarkable letter that Roosevelt wrote to Senator Henry Cabot Lodge that spelled out the qualities that he was looking for in a justice. An excerpt from my post:

It is essential, Roosevelt argued, that a justice be a “party man, a constructive statesman” in the “higher sense” of those concepts…. In the next two paragraphs [of his letter], Roosevelt’s “higher sense” of what it means for a justice to be a “constructive statesman” suddenly descends into the question whether Holmes agrees with Roosevelt on every political matter that Roosevelt regards as important….
Foremost among such matters was the question whether the residents of the newly acquired American territories of Puerto Rico and the Philippines should have the full rights of American citizens. Roosevelt was adamant that they should not, as was Lodge. The Court, in a series of rulings in 1901 in the so-called Insular Cases, had sharply divided 5 to 4 in favor of Roosevelt’s imperialist position, but the issue was not entirely settled. In his letter to Lodge, Roosevelt condemned the dissenters for their “reactionary folly [that] would have hampered well-nigh hopelessly [the American] people in doing efficient and honorable work for the national welfare, and for the welfare of the islands themselves, in Porto Rico and the Philippines.”
In sum, Roosevelt held a deeply political view of the role of Supreme Court justices. He could maintain, and perhaps even convince himself, that his view was political only in a “higher sense” of that term. But as his vigorous stance on the Insular Cases revealed, his view extended to all sorts of matters on which faithful Americans could have very different understandings of “the principles and policies under which this nation has been built up and in accordance with which it must go on.”

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