A longtime thorn in the side of the Obama administration’s immigration policy got the first chance to stick it to the president Monday, arguing in court that his sweeping immigration order — designed to spare nearly 5 million people from deportation — is unconstitutional.

Arizona county Sheriff Joe Arpaio and his attorney Larry Klayman argued before U.S. District Judge Beryl Howell in Washington, D.C., in the first courtroom hearing for a case against the immigration actions.

“We have serious issues of constitutionality involved,” attorney Larry Klayman told reporters, after the hearing.

Howell, during the hearing, seemed skeptical of the lawsuit brought by Arpaio, the Maricopa County sheriff known for his tough approach to illegal immigration.

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