For Arnold Giammarco, apprehended for several petty offenses and drug possession convictions, the prospect of deportation meant 18 months in a Massachusetts jail, before being sent to Italy, where he had not lived since he was age 4.

For Sayed Omargharib, taking two pool cues from a bar led to 22 months in detention and the memory of the weight of the shackles on his wrists and legs when immigration agents came to his house at 5 a.m. In the end, a federal appeals court decided officials had been wrong to hold him and set him free.

And for Sylvester Owino, it was nine years in detention until a federal appeals court decided to allow him to post bond. Now, he’s still in the United States – and still fighting deportation – though at least he can “breathe fresh air.”

On Wednesday, the United States Supreme Court will hear arguments in a case examining whether immigrants facing deportation from the US can get the small but potentially life-altering right to a bond hearing – and the opportunity to avoid years-long detentions as they await immigration hearings.

The case cuts to the notion of fairness within the deportation process – raising the question of how long someone guilty of nonviolent crimes should be allowed to be held in detention. But with President-elect Donald Trump mulling policies that could aggressively expand America’s already sprawling detention and deportation system, the stakes in the case have become that much higher.

Wednesday’s arguments will be a glimpse – for the first time in more than a decade – into how the high court sees the constitutionality of a key part of the US immigration system.

“We only expect that the Trump administration is going to increase the use of [immigration] detention,” says Sejal Zota, legal director at the National Immigration Project of the National Lawyers Guild. “The case certainly has even more import now, because it would ensure built-in constitutional protections for immigrants.”

The exploding detainee population

The case, Jennings v. Rodriguez, stems from a class action lawsuit against the federal government brought by Alejandro Rodriguez and other detained immigrants. It concerns whether certain immigrants are entitled to a bond hearing after being detained for more than six months.

In the decade since the high court heard a major immigration detention case, the legal and political landscape has changed significantly. The federal government has ramped up detentions as a means to increasing deportations, and Jennings will give the court a chance to react to these developments.

Between 1995 and 2016, the average daily immigration detention population grew from 7,475 to almost 33,000, according to a recent report from the American Civil Liberties Union (ACLU). A significant portion of these detainees are immigrants subject to “mandatory detention” statutes.

Under these statutes, the government can detain certain noncitizens targeted for deportation while their removal proceedings are ongoing, without having to justify their ongoing detention to a judge. Immigrants eligible for mandatory detention include legal permanent residents with criminal records and immigrants arriving at the US border for the first time.

Mandatory detention laws are in place ostensibly to prevent immigrants from going on the run during their deportation proceedings. And many detainees are deported within six months. But the ACLU argues the government is getting away with glaring violations of constitutional due process.

The government is “trying to make this an issue of border security, where we’re just talking about having a hearing,” says Cecillia Wang, director of the ACLU’s Immigrants’ Rights Project. “We’re talking about fundamental civil liberties issues.”

As the number of deportations has increased – with President Obama deporting more immigrants than every 20th century president combined – proceedings have become more focused. They are targeting those who have a weak case for staying.

Life in detention

A consequence of that, however, has been that those with strong cases against removal are often those who stay in detention the longest.

After his 18 months of detention, Mr. Giammarco decided to, in his words, “raise the white flag” and accept deportation to Italy.

A Connecticut resident for 50 years and a US Army veteran, he had struggled with drug addiction for several years. After leaving prison in 2008, he got a job at McDonalds, became a father, and on July 4, 2010, married Sharon, his US citizen wife.

Courtesy the Giammarco family Arnold Giammarco with his wife, Sharon, and daughter.

They had been living together for about a year when Immigration and Customs Enforcement (ICE) officials arrested him. While in detention, his appeals drained the couple’s personal savings, their daughter’s college fund, and $25,000 of his parents’ savings.

“He was changing as a person, just becoming depressed. We could see pain and agony in his eyes,” says Mrs. Giammarco. “I couldn’t imagine him in that place for another year, another day.”

“We made a decision: I would rather have him free in Italy than locked up here,” she adds. “At least we could call him if we wanted, and go visit him if we could. We’d figure out something from there.”

For Mr. Omargharib, it was the courts that changed course. The Washington hairdresser, a green-card holder for 28 years, recalls getting sick during his 22 months in the detention center and, as the weeks dragged on, he lost his job, his cars, and his house. He’s now unemployed and living with another former detainee in Richmond, Va.

If he had received a bond hearing after six months of detention, he says, his life would be different.

“If I had got out I’d have my job, I’d be OK,” he says.

How the courts have ruled

The US Court of Appeals for the Ninth Circuit seemed to agree when it ruled in 2013 that certain immigrants subject to mandatory detention must receive a bond hearing in after six months.

“While ICE is entitled to carry out its duty to enforce the mandates of Congress,” a three-judge panel of the Ninth Circuit wrote, “it must do so in a manner consistent with our constitutional values.”

In its appeal to the Supreme Court, the Obama administration is arguing that the Ninth Circuit has “rewritten” the laws governing immigration detention with a “radical” decision.

In 2003, the Supreme Court ruled that the government can detain deportable immigrants without bond during “the limited period necessary for their removal proceedings.” But in that ruling, Demore v. Kim, the court cited government data showing that the average detention period in such cases was roughly four months – data that the Justice Department admitted in August was wrong. Its new estimate puts the average detention period at more than a year.

Justice Anthony Kennedy, in particular, “seemed to assume certain things in the Demore case,” says Muzaffar Chishti, head of the Migration Policy Institute’s New York office. “How he reacts to the new information presented to the court [will be] important to see in the final outcome of the case.”

The justices could find consensus around a narrow, technical decision. But if there is a broader decision, in either direction, it will have a significant impact on the future of US immigration policy.

A 'modest first step'

ICE is currently holding over 40,000 people in immigration detention centers – more than it ever has before – and 5,000 more detainees are expected to enter the system over the coming months. Mr. Trump, meanwhile, has said he plans to deport up to 3 million immigrants with criminal records – a plan that would require “a massive – and costly – expansion of America’s prison and detention infrastructure,” according to the Southern Poverty Law Center.

A bond hearing would be a “modest first step” toward reining in such an expansive vision, says Christina Fialho, executive director of Community Initiatives for Visiting Immigrants in Confinement (CIVIC).

During the nine years that Mr. Owino was detained, immigration officials repeatedly denied his requests for bond, calling him a flight risk and a threat to public safety. He had already served two years in state prison for robbing a convenience store in 2003.

While in detention, Owino’s parents, and then his brother, died. He watched as his friends were either freed or deported. “When I hit the seven-year mark I was like, ‘This is too much.’ ”

In 2014, the Ninth Circuit finally granted Owino a bond hearing. The immigration judge who heard his case in 2015 released him on a $1,500 bond, which was paid for by funds raised by CIVIC.

Today, Owino lives in San Diego, where he runs a food stall at the local farmer’s market while his case continues to be processed through the courts. He’s ready to keep fighting to remain in the US.

To Owino, a win for Mr. Rodriguez in Wednesday’s Supreme Court case would be one important step toward ensuring fewer people have to go through what he did.

“Realistically I could have been out a long time ago,” Owino says. “I could have been living my life.”

Staff writer Jessica Mendoza contributed to this report.