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Judge Sonia Sotomayor has written three published opinions on federal taxation, one as a District Court judge and two as a Court of Appeals judge. Two of the opinions deal with routine matters and are unremarkable in the sense that it is difficult to imagine the cases coming out any other way. Her third opinion, however, in William L. Rudkin Testamentary Trust v. Commissioner, 467 F.3d 149 (2d Cir. 2006), aff'd sub nom. Knight v. Commissioner, 552 U.S. 181, 128 S. Ct. 782 (2008), generated a sharp difference of opinion with Chief Justice Roberts. Although Chief Justice Roberts, writing for the Supreme Court, affirmed the result in this third opinion, he criticized Judge Sotomayor’s reasoning (despite the fact that both the Solicitor General and the Department of the Treasury had endorsed it) and offered instead a different rationale. After a careful reading, I find the rationale of Judge Sotomayor’s opinion as least as valid as, and probably preferable to, that of Chief Justice Roberts. I also find Chief Justice Roberts’ criticism of Judge Sotomayor’s rationale logically flawed and therefore unwarranted.

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124 Tax Notes 1-4 (2009)