They could fall short again in 2020 despite winning the White House, then could be going against strong headwins in 2022 and 2026. I suppose they could win in 2024 to coincide with a Democratic President's reelection.
Maybe, but how Gill v. Whitford turns out will factor in quite a bit here. Should SCOTUS side with the plaintiffs and a test be developed, there will be a huge wave of partisan gerrymandering lawsuits starting next year. A lot of Republican-drawn maps will be softened up for 2020 if that is the case.
However putting that aside, coming up short in both 2018 and 2020 would require some exceptionally weak performances. We're talking about 24 seats here, and if Democrats couldn't win that many with both a favorable midterm and a favorable presidential election happening consecutively, well, I wouldn't even know what to say.
I think you need to be prepared for a big let-down vis-ŕ-vis Gill v. Whiford. Don't underestimate the party loyalty of the five Republican Justices -- Roberts, Kennedy, Thomas, Alito, and Gorsuch. Don't forget what happened in Dec. 2000: Bush v. Gore.
Just substitute Roberts for Rehnquist, Alito for O'Connor, and Gorsuch for Scalia, and it's the same bunch who stole from Al Gore his right to find out whether he actually won or lost.
First, Kennedy is far from a Republican justice. I think the odds Kennedy overturns the Wisconsin map at least in part are fairly good.
Second, you have no idea what the Bush v Gore decision was about. If the Supreme Court had decided in favor of Gore, then the Florida delegates would not have been able to vote in the electoral college, thus robbing Florida's citizens of the right to vote for president. The election would have gone to the house, where Gore almost certainly would have won. There had been two recounts already, and there was no legal standing for ordering a third. It was a blithering and pathetic partisan dissent that stands as by far Ginsburg's worst decision. Gore lost Florida either way but the issue at hand had absolutely nothing to do with 'allowing Gore to find out whether he won or lost'.
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