No State ever ratified the 16th amendment.
The several state legislatures ratified the Sixteenth Amendment
on the following dates: Alabama, August 10, 1909; Kentucky, February 8,
1910; South Carolina, February 19, 1910; Illinois, March 1, 1910;
Mississippi, March 7, 1910; Oklahoma, March 10, 1910; Maryland, April 8,
1910; Georgia, August 3, 1910; Texas, August 16, 1910; Ohio, January 19,
1911; Idaho, January 20, 1911; Oregon, January 23, 1911; Washington,
January 26, 1911; Montana, January 27, 1911; Indiana, January 30, 1911;
California, January 31, 1911; Nevada, January 31, 1911; South Dakota,
February 1, 1911; Nebraska, February 9, 1911; North Carolina, February
11, 1911; Colorado, February 15, 1911; North Dakota, February 17, 1911;
Michigan, February 23, 1911; Iowa, February 24, 1911; Kansas, March 2,
1911; Missouri, March 16, 1911; Maine, March 31, 1911; Tennessee, April
7, 1911; Arkansas, April 22, 1911 (after having rejected the amendment
at the session begun January 9, 1911); Wisconsin, May 16, 1911; New
York, July 12, 1911; Arizona, April 3, 1912; Minnesota, June 11, 1912;
Louisiana, June 28, 1912; West Virginia, January 31, 1913; Delaware,
February 3, 1913; Wyoming, February 3, 1913; New Mexico, February 3,
1913; New Jersey, February 4, 1913; Vermont, February 19, 1913;
Massachusetts, March 4, 1913; New Hampshire, March 7, 1913 (after having
rejected the amendment on March 2, 1911). The amendment was rejected
(and not subsequently ratified) by Connecticut, Rhode Island, and Utah.
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the supreme court twice declared the income tax unconstitutional.
Since its ratification in the form of the 16th Amendment? What cases were those? If you mean some pre-ratification SC decision, then we might as well argue that Plessy v. Ferguson invalidates Brown v. Board of Education.