For as long as the 27th Congressional District in Texas has been embroiled in litigation over whether it was racially gerrymandered, Nick Gilby has been working on Democratic Party campaigns there. Those seven years, he says, have been “like banging your head against a wall to see if you can move it.”

“He wins 60 percent of the vote or more every time, regardless of who the candidate is,” adds Mr. Gilby, referring to former Rep. Blake Farenthold, the Republican who held the seat from 2010 until he resigned earlier this month amid sexual harassment allegations and an ongoing ethics investigation.

Gilby’s frustrations are shared by William Whitford, a Democratic voter in Wisconsin, and John Benisek, a Republican voter in Maryland. There’s also Lorraine Petrosky, a Democratic voter in Pennsylvania, and Ersla Phelps, a Democratic voter in North Carolina. All four have told the United States Supreme Court this year that they feel, for various reasons, disenfranchised. Their state legislatures, they argue, redrew their district in a way that means their vote no longer matters.

In a year marked by several potentially landmark decisions, the most significant could be in the trio of gerrymandering cases the high court has reviewed – the last of which is being argued Tuesday.

Gerrymandering, the strategic redrawing of political district maps to advantage a candidate or party, is more than two centuries old. But with the rise of big data and advanced computing, gerrymandering has never been easier or more effective, experts warn, and is only expected to get more sophisticated. If the justices don’t establish new guardrails, the 2020 Census – and a new round of redistricting – will bring “a festival of copycat gerrymandering the likes of which this country has never seen,” a lawyer for Mr. Whitford told the Supreme Court last October.

The Supreme Court has responded. On Tuesday, the justices will return to the well-trodden issue of racial gerrymandering – where a district is found to be unlawful because it was drawn in a way that harms the voting power of minorities. Perhaps more strikingly, they also took the rare step this term of hearing two cases concerning partisan gerrymandering, one by Republicans in Wisconsin and one by Democrats in Maryland. It is legal, to a degree, for legislatures to redraw districts in a way that benefits them. Wary of becoming over-involved in local politics, the high court in the past has been reluctant to weigh in on when and how the exercise of redistricting ceases to pass constitutional muster.

But with another census less than two years away, “this could be the final word the court says this decade on redistricting,” says Michael Li, a senior counsel at the Brennan Center for Justice at New York University Law School.

“It’s going to be a blockbuster term for redistricting cases, running the gamut from race to politics,” he adds. “They clearly want to do something. Exactly what that looks like we’ll find out.”

Every new round of redistricting involves a certain degree of partisan gerrymandering: The majority party in a state has a right to redraw political maps in a way that benefits them – up to a point. While the Supreme Court in both 1985 and 2004 acknowledged that redistricting can be so partisan as to become unconstitutional, on both occasions the justices said they couldn’t identify where that line is and what the remedy would be.

Partisan gerrymandering

The court took another look at the issue this term with Gill v. Whitford, a case concerning the statewide political map approved by Republicans in the Wisconsin State Assembly in 2011.

In the 2012 election, Republicans won 60 of the 99 seats in the Wisconsin Assembly despite only winning 47 percent of the statewide vote. In 2014 they won 63 seats with 57 percent of the vote, and in 2016 they won 64 seats with about 53 percent of the vote. In a 2-to-1 decision, a three-judge federal district court panel found the redistricting plan unconstitutional, writing that the 2011 map “secured for Republicans a lasting Assembly majority [such that] in any likely electoral scenario, the number of Republican seats would not drop below 50 percent.”

When the Supreme Court heard arguments in the case, the justices seemed to agree that partisan gerrymandering is, as Justice Samuel Alito phrased it, “distasteful.” But they seemed to agree on little else after that.

“If you can stack a legislature in this way, what incentive is there for a voter to exercise his vote?” said Justice Ruth Bader Ginsburg. That larger concern with partisan gerrymandering, she added, is “something that this society should be concerned about.”

Chief Justice John Roberts, meanwhile, voiced concerns about whether the court should weigh in at all. “We will have to decide in every [future] case whether the Democrats win or the Republicans win,” he said. “That is going to cause very serious harm to the status and integrity of the decisions of this court in the eyes of the country.”

The overriding concern of many justices, however, was the concern that dates back to 1985: what standards the court could create to test when partisan gerrymandering occurs.

“If we are going to impose a standard on the courts,” Alito said, “it has to be something that's manageable and it has to be something that's sufficiently concrete so that the public reaction to decisions is not going to be the one that [Chief Justice Roberts] mentioned.”

When the court announced a month later that it would hear a second partisan gerrymandering case, Benisek v. Lamone, observers speculated that the justices would use it to iron out questions they had been unable to in Whitford. In particular, the Republican voters in Maryland’s 6th Congressional District are asking a question of particular interest to Justice Anthony Kennedy, who is considered a pivotal vote on the issue.

In the 2004 case, Justice Kennedy said that citizens have a First Amendment right to not be penalized for their past “associations with a political party,” which is precisely what the Maryland voters are claiming Democratic lawmakers are doing.

That appears to be a core question for Kennedy. If a state has a law or constitutional amendment saying redistricting “must be used in a way to favor party X or party Y,” he said during the Whitford argument, “is that lawful?”

Then “suppose the Maryland Constitution had a provision that required that partisan advantage for one party be the predominant consideration in any districting,” he said during the Benisek argument. “Lawful or not?”

If anything, the Benisek argument may have muddied the waters for the justices by putting the same issue in an entirely new context. While the Whitford case concerned an entire state map, the Benisek case only concerned a single district. While the Whitford case concerned claims of an Equal Protection violation, the Benisek case concerned claims of a Free Association violation.

These variations mean that, even if the court found a way to remedy the partisan gerrymandering in Maryland, “that’s not going to solve the other cases,” Justice Stephen Breyer said.

Furthermore, he noted that map drawers “are not stupid.” Technology is getting sophisticated enough that states could find new ways to gerrymander that the court has never seen before.

“If you think what's happened now is something, wait until you see those computers really working,” he said.

While there may be five justices who want to do something to address partisan gerrymandering, Amy How wrote for SCOTUSblog, the Benisek argument “once again demonstrated why [the issue] has vexed the justices for so long.”

Racial gerrymandering

For the final gerrymandering case of the term, the justices will be on more familiar legal ground.

While the Supreme Court has always recognized that some degree of partisan gerrymandering is acceptable, it has never done so for racial gerrymandering. The consistent challenge with these cases is determining whether the map drawers intended to create districts that diminish the voting power of minorities.

The case being argued tomorrow has spent seven years – and three elections – working its way up to the high court.

After the Republican-controlled Texas Legislature passed a redistricting plan in 2011, Democratic politicians and minority groups sued, claiming the new maps intentionally diluted Latino and African-American voting strength. (Those two racial groups accounted for 65 percent and 25 percent, respectively, of the state’s population growth between 2000 and 2010.)

With an election looming in 2012 and the lawsuit still pending, a federal district court in Texas ordered an interim map – which made some changes to the 2011 map, but left other parts the same – to be used in the election. A year later, the Legislature voted to adopt the interim map on a permanent basis.

The litigation continued, however, and in August 2017 a three-judge panel of the federal district court ruled that the 2013 map violated both the Constitution and the Voting Rights Act. The 27th District is one of those that has remained unchanged since 2011, and hundreds of thousands of Latino voters continue to be harmed by it, the parties behind the lawsuit claim."

In 1982, heavily Latino Nueces County was part of a new, solidly blue CD-27, which Democrat Solomon Ortiz held for 27 years. After Mr. Farenthold beat him by less than a point in the 2010 tea party wave, the 2011 redistricting dropped Nueces County into a redefined, red CD-27, removing its political sway.

“Nearly a quarter-million Latinos in Nueces County,” the appellees write in their brief, “are submerged in a sea of Anglo bloc voting.”

The state argues that it adopted the district court’s interim map, assuming that, since the map was drawn by a federal court, it had no legal problems. “A legislature does not engage in racial gerrymandering (or intentional vote dilution) by embracing, as its own, districts that a federal court ordered the State to use,” the state says in its brief.

In the new CD-27, the Latino population dropped from 73 percent to 51 percent. That made it difficult for Democrats to even challenge Farenthold for the district.

After winning the district by less than a point in 2010, he won re-election in 2012 by 17 points. To challenge Farenthold two years later in the veteran-heavy district, Democrats recruited Wesley Reed, a US Marine Corps pilot and lieutenant colonel. Farenthold won by 30 points, in a low-turnout midterm election.

Ever since Gilby started working campaigns here, he says, the district has been involved in litigation. “We thought, ‘OK we’re running in this district now, but it could be a very different district come next week,’ ” he says. “But nothing ever happened. It just stayed the way it was and it’s stayed that way ever since.”

The Supreme Court will bring him – and voters in Wisconsin, Maryland, and North Carolina – some form of closure later this year.

When the court failed to issue firm guidelines in either 1985 or 2004, state lawmakers “saw it as green light that they could go to town in terms of gerrymandering,” says Mr. Li of the Brennan Center.

“I think the court is worried that if it deadlocks again, or doesn’t provide clear guidance, that it’ll be an even stronger signal that you can do whatever you want,” he adds.

“I saw signals [earlier this term] that the court understands the magnitude of the problem, and understands that they’re partly responsible for it,” he continues. “These are hard issues, even for the Supreme Court.”