A family was awarded $1.5 million after US border officers wrongfully detained their 9-year-old. Their lawyer shares which AI tool helped him win the case.
Some lawyers continue to fall for made-up cases generated by artificial intelligence. Others are quietly finding ways to make the technology work for them.
Joseph McMullen, a San Diego civil rights and criminal defense attorney, is one of them. Last year, he said, he used AI-powered legal software to help him win a major case by sifting through evidence and making his filings more persuasive.
The case that led McMullen to rethink his tools started with a 9-year-old girl, a passport photo, and a border agent who thought something didn't add up.
In 2019, Julia, a fourth grader, and her 14-year-old brother, Oscar, rose early every weekday morning to cross the US-Mexico border to go to school. The siblings were born in the US but lived in a Tijuana border town, court records show. For local kids, the commute was as familiar as brushing their teeth.
They'd crossed the border many times without incident until March 18, when a US Customs and Border Protection officer noticed a dot on Julia's passport photo that looked like a mole she didn't have in person.
Julia was taken to a secondary inspection area and interviewed alone, which the court would later find violated the agency's policy on questioning children. In a lawsuit, the family alleged that border officers pressured her to claim she was her Mexican cousin.
The government denied any coercion and argued that the length of the children's detention was justified because Julia repeatedly identified herself as her cousin. A Customs and Border Protection spokesperson declined to comment.
Julia was detained for 34 hours, and Oscar for roughly 14 hours, before they were reunited with their mother.
Swearing off ChatGPT
As he built his lawsuit against Customs and Border Protection over the children's detention, McMullen, who runs his own law practice, turned to technology to interpret the evidence.
By early 2024, he had three federal civil trials in three months. Time was short, and help was scarce.
He approached tools like ChatGPT with deep skepticism. In one of his early tests, the chatbot surfaced a case that seemed perfect — until he realized it didn't exist. "That was it. Never again," he said.
Barely a month went by without another story of a lawyer getting burned by bogus case law. Judges were catching on. A public database maintained by legal data analyst Damien Charlotin lists 120 cases where courts caught lawyers using fake or hallucinated citations. Most of the cases were in the US in the past 18 months.
Still, the idea of using AI stuck with McMullen. Unlike lawyers who lean heavily on case law, he spends most of his time combing through police reports, surveillance footage, transcripts, and emails, then figuring out what he has, what's missing, and what story the evidence tells.
He wondered how better tech could help him, like taking a metal detector to a haystack.
Get to the point
There was no jury in his trial against CBP, which meant US District Judge Gonzalo Curiel would make the decision.
That made written filings even more crucial. "It was important to make it as easy as possible for [Curiel] to get the information that I really wanted him to look at," McMullen said.
Another attorney recommended Clearbrief, a tool that integrates with Microsoft Word and lets lawyers link every factual claim to the underlying evidence. The plugin recognizes citations using natural language processing and automatically generates links to relevant case law or documents.
When an attorney files a brief using Clearbrief, a judge or any recipient can open a hyperlinked version in Word or a browser. Each citation becomes interactive: Clicking on one pulls up the exact source text side-by-side with the brief, allowing the reader to verify claims faster without digging through exhibits or databases.
While preparing for trial, McMullen found a California unlawful detainment case that had resulted in a large damages award. To try and steer Curiel toward a similar judgment, he used Clearbrief to link an appellate brief from that case — buried deep in a district court docket — directly in his trial memo.
McMullen said being concise in briefs is not just about saving time; it is a persuasive strategy in itself.
Effective advocacy, he said, isn't about "inundating a finder of fact with all the evidence," but presenting "the most important things that you need to know." (He's certain Curiel and his clerks were thorough in their review.)
"Being efficient with anyone's time is persuasive," he said.
Clearbrief and the competition
Lawyers can also use Microsoft Word to hyperlink text.
The Clearbrief difference, founder and CEO Jacqueline Schafer said, is that it automatically creates the hyperlinks and checks the citations against databases like LexisNexis and vLex Fastcase. The tool flags any mismatch between what the lawyer writes and what the source says.
Schafer said it speeds up drafting and reduces the burden on judges to confirm that every citation is accurate and not the product of an AI hallucination.
Clearbrief's client list includes law firms, courts, and legal departments with names like Hogan Lovells, Microsoft, and the American Arbitration Association. The service starts at $200 a month per user for solo practitioners and small teams, with higher rates for larger organizations.
Westlaw and LexisNexis also offer tools to assist with legal research and drafting, but they don't affect how the final document appears to the court or recipient.
Another Clearbrief feature McMullen relied on was timelines. The tool turned over dozens of depositions and other records and created a case chronology, complete with hyperlinks to the source documents that support the dates and events shown in the timeline.
McMullen didn't submit the timeline in court — it was "maybe a thousand lines" — but he read it closely in trial prep to make sure he hadn't missed anything.
Better outcomes
Last year, Curiel ruled that CBP falsely imprisoned the siblings and was liable for the "intentional infliction of emotional distress" in the 2019 incident. Oscar's grades went down. Julia suffered from insomnia and nightmares. Their parents sought therapy for them both.
Curiel wrote in his decision that the government's conduct was "beyond the bounds" of what is "usually tolerated in a civilized community. " He ruled that the agency must pay the family $1.5 million in total damages.
The US government appealed the decision, then dropped its appeal.
Many legal tech startups promise lawyers they'll be able to take on more cases. For McMullen, the promise of AI isn't about churning through more cases so much as going deeper on the ones he has. He said he used the time he saved to visit Julia's family in Mexico.
"There are several aspects of the practice that are gratifying," McMullen said. But, "there's not a single person who says, 'I really love the tedium of formatting that table.'"
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They'd crossed the border many times without incident until March 18, when a US Customs and Border Protection officer noticed a dot on Julia's passport photo that looked like a mole she didn't have in person. Julia was taken to a secondary inspection area and interviewed alone, which the court would later find violated the agency's policy on questioning children. In a lawsuit, the family alleged that border officers pressured her to claim she was her Mexican cousin. The government denied any coercion and argued that the length of the children's detention was justified because Julia repeatedly identified herself as her cousin. A Customs and Border Protection spokesperson declined to comment. Julia was detained for 34 hours, and Oscar for roughly 14 hours, before they were reunited with their mother. Swearing off ChatGPT As he built his lawsuit against Customs and Border Protection over the children's detention, McMullen, who runs his own law practice, turned to technology to interpret the evidence. By early 2024, he had three federal civil trials in three months. Time was short, and help was scarce. He approached tools like ChatGPT with deep skepticism. In one of his early tests, the chatbot surfaced a case that seemed perfect — until he realized it didn't exist. "That was it. Never again," he said. Barely a month went by without another story of a lawyer getting burned by bogus case law. Judges were catching on. A public database maintained by legal data analyst Damien Charlotin lists 120 cases where courts caught lawyers using fake or hallucinated citations. Most of the cases were in the US in the past 18 months. Still, the idea of using AI stuck with McMullen. 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The Guardian asked Ice, TransCor and CoreCivic about the incident – including whether vans and buses transporting immigration detainees are equipped with cameras. Ice and TransCor did not respond. Ryan Gustin, senior director of public affairs for CoreCivic, said: 'At TransCor, the safety and security of the public, our staff, and those entrusted to our care are our highest priorities. To that end, we do not publicly disclose how the TransCor fleet is equipped, related to safety and security equipment.' Transportation of detainees is more under the control of private companies than in the past, said Katherine Culliton-González, chief policy counsel at Citizens for Responsibility and Ethics in Washington. TransCor president Curtiss D Sullivan titled the company's 2025 first quarter outlook 'The Time for Growth is Now'. CoreCivic's TransCor is not the only company growing its transport business under Trump; the Geo Group, which runs 16 immigration detention centers across the country, also has a transportation subsidiary. Added to the privatization of services needed for Trump's mass immigration push is the decimation of agencies performing federal oversight of Ice – including the Office for Civil Rights and Civil Ciberties (CRCL) and the Office of the Immigration Detention Ombudsman (Oido), said Culliton-González. In this setting, 'how can we hold private companies accountable?' she said. The issue of oversight will be increasingly important as more health issues and deaths follow the increasing number of detainees being transported around the country. 'Ice right now is all about more people coming in, and pushing them through [to deportation],' said Dora Schriro, a consultant on immigration and former Ice official. 'As input/output grows – not just in size, but in speed – the likelihood of making mistakes is going to increase,' Schriro said. 'Ice should make sure every person they take from law enforcement is fit for travel – for the length and conditions of being transported.' Avellaneda Delgado was the first Ice detainee in at least a decade to die while being transported from a local jail to a federal detention center, said Free, who also wrote about the case for ACPC, an Atlanta-based digital outlet. Meanwhile, Avellaneda Delgado's children just spent their first Father's Day without him. The day was doubly difficult for the youngest because it was also his birthday. Heavy rains kept the family from visiting Avellaneda Delgado's grave. 'It bothers me,' Junior said. Then he added: 'He was a great grandfather.'
