4 Summer Election Days? New York Faces Chaos in Voting Cycle.

To understand the chaos upending New York’s election season, consider the plight of Marc Molinaro, the Dutchess County executive trying to run for Congress as a Republican somewhere near his home in the Hudson Valley.

Just two weeks ago, the state’s highest court unexpectedly invalidated the new congressional district in which Mr. Molinaro had spent months campaigning, throwing the battlefield into limbo as a special master redraws it and every other House seat in the state.

Then last week, his likely Democratic opponent, Representative Antonio Delgado, took a job as New York’s lieutenant governor. The departure will prompt a special election this summer to fill the district whose current contours will be gone by January, just months before November’s election on lines that do not yet exist.

“I’m a man in search of a horse,” Mr. Molinaro said in an interview on Wednesday. “I have no district, no opponent, and a million dollars.”

With control of the House of Representatives on the line, no one expected this year’s redistricting cycle to be an afternoon by the Finger Lakes. But to a degree few foresaw, New York is lurching through what may be the most convoluted election cycle in living memory, scrambling political maps, campaigns and the calendar itself.

It only got murkier this week, when Representative Tom Reed, a Republican from the Southern Tier of the state, announced that he would leave his seat earlier than expected to work for a Washington lobbying firm, setting up a second special congressional election this summer. (Mr. Reed decided not to seek re-election last year in the face of a groping allegation.)

What’s left behind is a fog of confusion over when people are going to vote, who is running in which districts and when Gov. Kathy Hochul will schedule two special elections that could have an immediate impact on the narrowly divided House of Representatives in Washington.

For now, neither Mr. Delgado nor Mr. Reed has officially resigned from their seats, according to the governor’s office.

“We are working with the lieutenant governor-designate’s team on the transition and have not yet received Congressman Reed’s resignation,” Hazel Crampton-Hays, a spokeswoman for Ms. Hochul, said on Wednesday. “But when we do, the governor will call a special election as required by law.”

It is not implausible that New York could hold Election Days for statewide and Assembly primaries on June 28; for congressional and State Senate primaries on Aug. 23; and for the seats of Mr. Delgado and Mr. Reed on separate Tuesdays in August. (Republicans believe that Mr. Delgado may be delaying his House resignation so that his district’s special election can coincide with the Aug. 23 primaries in an effort to boost Democratic turnout.)

“I joked with our staff last night, maybe tomorrow the locusts will set in?” said Nick Langworthy, the state Republican Party chairman. “We just have so many catastrophes politically.”

Some greater clarity may yet be on the horizon.

The court-appointed special master is scheduled to unveil the new congressional and State Senate districts on Monday, and if they are approved by Patrick F. McAllister, a judge in Steuben County, candidates will be able to begin plotting summertime campaigns.

On Wednesday, Judge McAllister, who is overseeing the redistricting case, shut the door on a related but belated attempt to strike down State Assembly districts. The judge also laid out the process by which candidates can qualify to run in the newly redrawn districts once they are unveiled.

If Republicans tend to view the absurdities in a more humorous light than Democrats do, it is because each change has played out to their benefit.

The lines passed by the Democrat-dominated Legislature in February, only to be struck down in late April by the New York State Court of Appeals, would have given Democrats a clear advantage in 22 of the state’s 26 congressional districts. While the new lines remain a mystery, they are widely expected to create more swing seats that Republicans could conceivably win.

The departure of Mr. Delgado in the 19th Congressional District was another unforeseen gift to the Republicans. While the exact shape of the new district will matter, Mr. Molinaro’s prospects will be enhanced by not having to run against a popular incumbent with a track record of winning tough races.

The district, which includes all or parts of 11 counties, has been one of the state’s most competitive, with tight races in 2016 (a Republican win for John Faso), and in 2018, when Mr. Delgado won his first term. Mr. Delgado won by a more comfortable margin in 2020 against Kyle Van De Water, a Republican and former officer in the U.S. Army.

The leading Democratic contender is Pat Ryan, the executive of Ulster County, across the Hudson River from Mr. Molinaro. Mr. Ryan hasn’t formally declared his candidacy but said he was “aware of the urgency” following the news of Mr. Delgado’s appointment and expected to make a decision within days.

At the same time, he seemed somewhat amazed by the various moving pieces of this election cycle, including the changing congressional lines.

“In an ideal world, I would know what district I would be running for, certainly,” Mr. Ryan said, adding, “I studied political science, but this wasn’t in any of the textbooks.”

The situation in Mr. Reed’s old seat, the 23rd Congressional District, is less likely to affect the partisan makeup of the House, but it has twisted Republicans into an odd bind.

Democrats had largely preserved the existing right-leaning district under the plan that was struck down in court, even as they reshuffled the lines of other Republican seats like the one held by Representative Claudia Tenney. The changes prompted Ms. Tenney, who represents Utica, to declare her candidacy for the Southern Tier seat this spring, and she appeared destined for re-election in her new district.

That path is no longer clear. Republicans once deferential to Ms. Tenney may dive into the race, seeing a chance to win a short-term seat in Congress and move into prime position in a future party primary for the newly drawn seat. Or the race could be more or less meaningless, if the special master totally reconfigures the district.

“You could have people who looked at it once, get back in,” Mr. Langworthy said. He added that he would advise even Ms. Tenney to hold tight for now.

“The winds of change could end bringing her right back to Utica,” he said.

Ms. Tenney’s campaign did not respond to a request for comment.

Joe Sempolinski, a former Reed aide and local Republican county chairman, has already put his name forward as a candidate for the special election.

For his part, Mr. Molinaro, who ran unsuccessfully for governor in 2018, says he’s as almost as befuddled as voters by the changing shape of the state’s congressional campaigns.

“Whatever’s complicated, complex and corrupt someplace else,” he said, “is much worse in New York.”