DETROIT (AP) — U.S. Rep. John Conyers, No. 2 in seniority in the House of Representatives, lost his appeal Friday to get on the August primary ballot after Michigan election officials found problems with the Democrat’s nominating petitions.

The Secretary of State’s office affirmed a decision by Detroit-area election officials to keep Conyers off the ballot. It would end his 50-year career in Congress unless courts intervene or he runs a successful write-in campaign.

A federal judge is expected to rule later Friday on Conyers’ request to throw out a Michigan election law as unconstitutional.

Conyers, 85, had appealed to the state after Wayne County officials said there were problems with some people who collected signatures. The circulators weren’t registered to vote or had listed a wrong registration address.

That can spoil petitions, under Michigan law, and as a result Conyers lacks the 1,000 signatures necessary to get on the ballot.

Killing Conyers’ career that way is “pretty outrageous,” his lawyer, John Pirich, said this week.

Political opponents aren’t upset. An attorney for a Democratic challenger, the Rev. Horace Sheffield III, said Conyers for decades had no problem following the law.

“In essence, they played the game, lost and then complained that the rules were unfair,” Eric Doster said, quoting a Virginia judge.

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Judge Overturns Mich. Election Officials Decision, Allows Rep. Conyers on Ballot