The U.S. Supreme Court on Tuesday heard arguments in Gill v. Whitford, the first of many cases before the Court this term that challenge electoral restrictions and gerrymandering efforts. And it was a doozy of an oral argument.

First, some background. This case involves a challenge to the redistricting plan adopted in 2011 by Wisconsin’s Republican-controlled legislature. A federal court struck down the plan in 2016, ruling it unconstitutional because it was the product of partisan gerrymandering, a practice of purposely drawing district lines to favor one political party at the expense of another. The court blocked Wisconsin from using that map and told it to adopt a new redistricting plan by November 1, 2017. The State of Wisconsin then appealed that ruling to the Supreme Court, which agreed to take the case but stayed the order blocking the redistricting maps.

In this case, the challengers, led by retired law professor William Whitford, argue that the redistricting plan would allow Republicans to maintain control of the state’s legislature, even if the party falls out of political favor. In other words, it’s become almost impossible to elect a Democrat to office, they allege. According to the challengers, the federal district court’s decision corrected “a serious democratic malfunction that would otherwise have gone unremedied.”

According to the parties challenging the maps, Wisconsin Republicans used two gerrymandering techniques to ensure this captured political power. The first, they claim, was that the map was drawn to “pack” Democrat voters into a small number of districts. The challengers also claim that Wisconsin lawmakers then “cracked” other Democrat voters into several other districts in a way that would ensure Democrats would fall just short of a majority. All in all, the challengers say, the excess votes for a winning candidate in a packed district, and the votes for a losing candidate in a cracked district, are “wasted.” Unsurprisingly, the challengers allege, the wasted votes for the Democrats far outnumber those for Republicans. And all of this, they say, amounts to an unconstitutional partisan gerrymander.

Attorneys for the State of Wisconsin, however, argue that if the lower court’s decision is allowed to stand, it will open the door to “unprecedented intervention [by the federal courts] in the American political process.” The state also argues that the 2011 redistricting plan does not violate the Constitution, because politics was only one of many factors the legislature considered in drafting the new electoral map. The state insists this “complies with traditional redistricting principles.” The state also argues that the challengers lack standing to challenge the redistricting plan.

Courts have typically shied away from taking on questions involving political, rather than racial, gerrymandering. That is in part because those disputes are traditionally considered “political” questions that the legislature should decide, not the courts. But more and more states have claimed their efforts to draw legislative districts are not racially discriminatory, but rather part of a longstanding practice that the winning party gets to draw electoral maps as it sees fit. In other words, conservatives have tried to argue, their political gerrymandering is allowed under the law even if it at times overlaps with racial gerrymandering.

The Supreme Court really does not enjoy jumping into gerrymandering cases, and the look of exasperation on many of the justices’ faces, in addition to the difficult and pointed questions they posed to the attorneys Tuesday, proved that exact point.

Attorney Misha Tseytlin of the Wisconsin Department of Justice argued first, telling the justices that the challengers in this case are trying to kick the redistricting process from the state legislature to the courts, which would place judges in the position of deciding “the fate of maps based upon battles of the experts.” The case, he said, represents a “redistricting revolution.”

Tseytlin did not get much further into his argument before Justice Anthony Kennedy—the likely swing vote in the case—began to pepper him with questions.

After Kennedy asked whether the state’s gerrymandering attempts violated First Amendment guarantees of freedom of association, Justice Stephen Breyer, the Court’s data nerd, wanted to know if there was some easier way to get accurate numbers on how many voters were affected by the gerrymandered maps, noting that redistricting cases are very technical for courts to parse through.

Justice Elena Kagan then observed that technology advances have made the redistricting process even more sophisticated, giving partisan politicians more opportunity to try and manipulate it. Justice Sonia Sotomayor reminded Tseytlin that the state didn’t even produce any evidence at the trial court or to the Supreme Court that directly rebutted the challengers’ claims: that Wisconsin lawmakers drew three different possible redistricting maps and decided to choose the one most likely to keep Republicans in power for as long as possible. Justice Ruth Bader Ginsburg invoked the “precious right to vote,” asking whether people would bother to vote at all if they assumed their vote wasn’t going to count.

Needless to say, it appeared that Tseytlin has had better days at work.

Still, there is no guarantee the challengers will win here. When it came time for Attorney Paul Smith to argue on behalf of his clients, it became clear the conservative justices were looking for a way to rule that the challengers did not have standing to bring a claim against the gerrymander outside of their individual voting districts. Chief Justice John Roberts started the questioning by suggesting that if the Court rules in favor of the challengers, every legislative map drawn for redistricting will face a legal challenge that will eventually wind up before the Supreme Court.

Smith pushed back hard against the chief justice on this point, arguing the country was on the “cusp of a … more serious problem” that would produce a “festival of copycat gerrymandering” in 2020 if the Court rejected his clients’ claims. Then, Smith said, every state would end up as gerrymandered as Wisconsin.

“Gerrymanders now are not your father’s gerrymander,” Smith told the justices.

Oral arguments rarely provide a clear answer as to the outcome of any case, let alone one that has reached all the way to the U.S. Supreme Court. But if I had to guess, I’d say Wisconsin is going to lose here. The attorneys for the state barely disputed the fact that the legislative map chosen by lawmakers was the most partisan map they could create. Justice Samuel Alito said the challengers were painting “a very dire picture” of the electoral process, almost suggesting they should just lighten up.

But it will very likely be Justice Kennedy’s vote that will decide this case. And if his demeanor and questions were any indication of how he is leaning, Wisconsin Republicans should brace for a loss.

A decision in the case will likely come this spring, and if Kennedy does side with the liberal justices then there is even a chance that the Supreme Court could push back against the kinds of political power grabs Republicans in Wisconsin and elsewhere have made through the gerrymandering process. Almost 20 years after Bush v. Gore, the Supreme Court case that in 2000 singlehandedly delivered the presidency to Republicans, that would be a good result. But it’s certainly not a guarantee.