As cited in a 2012 WSJ blog and elsewhere, the granddaddy of these quotes is from the US Court of Appeals Fourth Circuit in 1994. Judge Erwin wrote:
There can be no doubt but that the statutes and provisions in question, involving the financing of Medicare and Medicaid, are among the most completely impenetrable texts within human experience. Indeed, one approaches them at the level of specificity herein demanded with dread, for not only are they dense reading of the most tortuous kind, but Congress also revisits the area frequently, generously cutting and pruning in the process and making any solid grasp of the matters addressed merely a passing phase.Picked up by Politico, Judge Gorsuch in California has made the same point in a new case.
This case has taken us to a strange world where the government itself — the very ‘expert’ agency responsible for promulgating the ‘law’ no less — seems unable to keep pace with its own frenetic lawmaking....One thing seems to us certain: An agency decision that loses track of its own controlling regulations and applies the wrong rules in order to penalize private citizens can never stand.In between this 1994 citation and the new 2016 one by Gorsuch, there is another case where Medicare is described as an inpenetrable labyrinth...Northeast Hospital Corporation v Sebelius, 2011, online here. Judge Griffith wrote,
We are thus faced with two inconsistent sets of statutory provisions...The usual rule that Congress intends different meanings when it uses different words has little weight here... Given Medicare's inconsistent and specialized use of [certain phrases]....[Quoting Judge Luttig, Cabell v Shalala 101 F3d 984, "Congress has consistently used [two different words] for no reason that anyone has been able to divine."] ...Because of a clerical error, the text of 412.106 was not revised...The Secretary admits she routinely failed to count [Medicare Advantage] days in the Medicare fraction...[and she] does not even attempt to reconcile these statements with her claim...We are aware of no statute that authorizes the Secretary to promulgate retroactive rules...[Quoting Judge Learned Hand] "[Does the text] have any significance save that the words are strung together with syntactical correctness?"_____
For a 2015 law review article on how confusing the Medicare ALJ system can be, here.