Business
Lawyers to the wealthy warn that AI legal advice comes with serious risks
Displeased couple having problems during a meeting with their agent in the office.
Skynesher | E+ | Getty Images
A version of this article first appeared in CNBC’s Inside Wealth newsletter with Robert Frank, a weekly guide to the high-net-worth investor and consumer. Sign up to receive future editions, straight to your inbox.
Lawyer Tasha Dickinson said she gets calls every week from clients asking about legal advice they got from ChatGPT, Claude or another artificial intelligence chatbot. Some don’t admit it, but she can tell from their line of questioning, she said.
One client, a high-net-worth Florida resident, asked Dickinson about creating a community property trust — an attractive option for married couples — saying he got the suggestion from AI to save on taxes for his heirs, she said. Dickinson quickly pointed out a problem: The client’s wife had recently died.
“I said, ‘Well, you do understand that a community property trust is between husband and wife, right?’ And there was silence on the phone,” said Dickinson, a partner at Day Pitney. “‘They’re like, ‘Oh, well, AI thought it was a good strategy.’ Well, like, in the universe, maybe it’s a good strategy, but it’s not a good strategy for you.”
Lawyers to the wealthy told Inside Wealth that their clients are increasingly using AI not only to research tax topics but to second guess their lawyers’ advice. While some lawyers said AI helps clients come up with informed questions and learn basic concepts, they also say it poses a headache and legal risks.
Robert Strauss, partner at Weinstock Manion, said several clients have uploaded trust documents to AI systems and come back with a list of questions and suggested edits, forcing Strauss to defend his work and explain why the AI recommendations aren’t appropriate for the client’s situation.
“The questions are fine, but it results in spending more time on the matter than we would ordinarily spend,” he said. “We end up spending two, three, four hours of time dealing with stuff that so far has amounted to nothing. I have not actually received a single workable suggestion from that process.”
The result, he said, is a lack of trust on the part of the client in their lawyer.
What’s more troubling, Strauss said, is that clients are sharing sensitive information with large-language models, raising data privacy concerns and legal pitfalls. Strauss said his firm is currently revising their client contract to warn clients that using AI chatbots like this can void attorney-client privilege.
In February, a federal judge ruled that a criminal defendant’s conversation with Claude about his legal defense strategy were not protected by attorney-client privilege.
“What’s keeping me awake at night as it relates to AI? It’s not that AI is sometimes wrong, because I can correct those mistakes. And it’s not that people are double-checking my work on AI, because I have a lot of confidence in my work,” Dickinson said. “What I am concerned about is that when people put documents and do these searches into AI, they’re waiving the attorney-client privilege, and that is a huge issue.”
Dan Griffith, director of wealth strategy at Huntington Bank, warned that asking a chatbot how to protect your assets with a prenuptial agreement or how to sell your business while paying less in taxes, for example, could be used against you in court.
While high-net-worth clients can generally access — and afford — the best legal advice, they, like the rest of us, enjoy the convenience of AI, according to Griffith.
Dickinson added that the cost savings are still a draw. (“It’s not fun to pay for professional services,” she said.) She added that many of her clients are confident entrepreneurs.
“A lot of our clients have been so successful. I mean, they’re smart, right? And they have a drive for knowledge,” she said. “I think some err on the side of assuming that they understand more about this than they actually do.”
Using these AI tools, she said, “gives a false sense of knowledge.”
In some ways, this isn’t a new problem. Clients often bring suggestions to their lawyer that they got from a country club friend or an article. Dickinson described it as “a more evolved form of cocktail party talk.”
And the trend isn’t one-sided. Many lawyers use AI in their professional and personal lives. This has led to headline-making blunders like briefs with fake citations.
But few clients are familiar enough with AI and the law to write an effective prompt, lawyers said.
Ed Renn of Withers gave the example of a client who wanted to transfer unlimited assets to his spouse upon ChatGPT’s advice. The client, however, didn’t mention his wife was foreign-born, which means he couldn’t take advantage of the unlimited marital deduction without a special type of trust, according to Renn.
“If you don’t know quite what you’re doing, it’s garbage in, garbage out,” he said.
Renn added that AI tools appear to make more mistakes with more complex topics like international taxes and aren’t up to date with new legislation or guidance from the Internal Revenue Service.
Griffith said that deciding how to transfer your wealth to your loved ones requires a more complicated discussion than ChatGPT is prepared for. There are rarely easy answers when deciding, for instance, how to divide assets between children from a first marriage and a second spouse, he said.
“If your client asks, ‘Hey, if I do this trust, will my son have access to the funds that I give him at some point in time?’ The answer shouldn’t be ‘yes’ or ‘no.’ The answer should be, ‘Tell me more about your relationship with your son, or what’s the situation like?'” he said. “AI tends to be very solution-oriented and tries to find some way to get to yes. It doesn’t do a good enough job of saying, ‘You know what? Let’s get to the core of what your question is.'”
Business
Spirit Airlines shutting down after rescue talks collapse
The earlier plan, which would have seen the US government take effective ownership of as much as 90% of the airline, faced stiff opposition from Wall Street, Capitol Hill and even a member of Trump’s own cabinet. Transportation Secretary Sean Duffy told Reuters a rescue would amount to tossing “good money after bad”.
Business
Spirit Airlines could shut down overnight. Here’s what travelers need to know
Spirit Airlines check-in Kiosks sit idle at Oakland International Airport on August 13, 2025 in Oakland, California.
Justin Sullivan | Getty Images
Spirit Airlines could shut down as early as 3 a.m. ET Saturday, according to people familiar with the matter. The carrier has failed to secure a financial lifeline to continue operating, though it hasn’t commented on the potential shutdown or its plans.
About 290 Spirit flights are scheduled for Saturday, according to aviation site Flightradar24. Another 381 are scheduled for Sunday.
Travelers with Spirit tickets could be understandably rattled. While there have been some U.S. airlines to shut down in recent years, the budget carrier is larger than most recent airline failures and links major cities like New York, Miami, Detroit and Los Angles — and many others in between — with its Airbus jets.
Here’s what travelers need to know:
You have a Spirit ticket. What should you do?
Immediately? Nothing.
Travelers who are booked on a Spirit flight, like this CNBC reporter is for later this month, are likely to receive a refund if they purchased tickets with a credit card.
If the ticket was bought with a debit card or with loyalty points, however, the chances of recovering funds are slim to none, said Henry Harteveldt, founder of Atmosphere Research Group, a travel consulting firm.
“If you’re holding a reservation for a flight on Spirit don’t proactively cancel it. Wait for the airline to announce it is shutting down,” he said.
Would Spirit be able to help you at the airport?
Don’t count on it.
Spirit has declined to comment on a potential shutdown. If it confirms an end to operations, the carrier will most likely have information on its website about travelers’ next steps.
Harteveldt said travelers shouldn’t go to the airport expecting to find Spirit staff in the event the airline ceases operations. Call centers are likely to be overwhelmed if they are still staffed.
That could leave passengers with fewer answers than they’d like, but other airlines are likely to help assist affected customers.
Airlines that offer last-minute fares, likely with some discounts, will be available to travelers at airport ticket counters.
How can another airline help?
United Airlines, JetBlue Airways, Frontier Airlines and American Airlines are among the carriers that have said they are ready to assist Spirit customers and crews if the carrier shuts down.
That could mean scheduling additional flights to carry the stranded passengers, similar to what they do during a hurricane or other natural disaster.
Why could Spirit shut down?
Spirit, known for bright yellow planes, low fares and fees for everything else, had been successful for years, but this week it’s been on the brink of liquidation after failing to reach a deal with bondholders for a $500 million government bailout from the Trump administration.
Last year Spirit filed for its second bankruptcy in less than a year, though it’s had a host of problems even before then.
A plan to be acquired by JetBlue was blocked. Rising costs upended its business model. An engine defect grounded dozens of its planes. And, more broadly, upscale travel became more popular with consumers, driving airline profits.
At the same time, big, legacy airlines were selling their own basic economy fares that were similar to what Spirit was offering, but with bigger networks.
What does this mean for travel going forward?
Airlines have been adding flights since Spirit’s bankruptcy filing last year on some of its routes and at major airports. They’re likely to keep doing so.
Experts have said they expect fares to rise, at least in some markets, if the discounter goes away, even though the carrier has shrunk substantially.
Business
Middle East crisis: Air India to make food optional, help cut price of tickets – The Times of India
NEW DELHI: Desperate times call for desperate measures. Full service Air India is planning to make meals optional on its domestic and short international (under two hour) flights. Once this “unbundling” rolls out in the next month or two, passengers opting out of meals could have upwards of Rs 250 shaved off their ticket price. While this move, say people in the know, is “on the anvil,” the airline is looking at several other unprecedented measures to fly through the severe cost-revenue turbulence caused by the unending West Asia war.While not opting for meals could lead to slightly cheaper economy tickets, AI is looking at unbundling lounge access for business class passengers because those opting out of this, could get their tickets cheaper. On an average, lounge operators charge Rs 1,100-1,400 per user at metro airports and Rs 600-700 at non metros.The average spend is about Rs 1,000 per lounge. Many business class flyers are frequent travellers who just make it to airports in time for their flight and do not head to the lounge. If unbundled, this could be a saving in their ticket cost. Banks have been reducing lounge access for credit card users for the same reason to cut their costs.“From Day One, Air India has had meals bundled in its ticket price. Now the way aviation turbine fuel (ATF) price is rising and the rupee crashing since Feb 28, ticket prices are going up. India is a price-sensitive market and raising fares beyond a point leads to a fall in traffic with many opting to travel by train or road. This has led to the rethinking to unbundle meals on some flights. Other steps are also being considered,” said people in the know.Several airlines globally have over the past few years unbundled their onboard offerings. Many international full service airlines offer a basic meal in economy while giving the option of buying gourmet meals at an additional cost. Ditto for alcoholic beverages, with cheaper beer and wines being given at no extra cost while the others being charged for. “For passengers, the distinction between full service and low cost airlines is blurring very fast,” said an industry old-timer.
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