Day: August 30, 2025

• Legendary singer Tony Bennett died in 2023 at age 96, after a long, lucrative career.
• The final version of a family trust he signed in 2016 excluded his daughters from estate decisions.
• They are suing their brothers after discovering Bennett’s estate has a gross value of only $7M.

He left his heart in San Francisco.

Less famously, and in the final years of his life, he left his daughters with no say over his fortune — fueling an estate battle that spans two Manhattan courthouses and is still raging two years after his 2023 death.

Legendary singer Tony Bennett was 90 years old and performing with his friend Lady Gaga at packed concert halls in late 2016, when he signed the final versions of his will and family trust. His widow and third wife, Susan Crow Bennett, would inherit $5 million, with the remainder of his multimillion-dollar estate to be split evenly among his four children.

There was no even split, though, when it came to running the estate.

Documents made public in the siblings’ ongoing war over his assets show that Tony Bennett favored his two sons (from his first marriage) over his two daughters (from his second marriage) when it came to managing the concert earnings and royalty revenue streams of his seven-decade career of recording and performing.

Under the 2016 trust agreement — signed by Tony Bennett in the same year he was diagnosed with Alzheimer’s, and with his attorney of three decades present as a witness — sons Danny and Daegal Bennett could manage his money as estate trustees in the years before and after his death, but daughters Johanna and Antonia could not.

Nor were the daughters entitled to any say over how the estate was run.

Johanna, 55, of New York City, and Antonia, 51, of Los Angeles, declined through a spokesman to comment on the ongoing estate battle.

But they argue in court papers that only after their father’s death did they learn there is just $12 million in the estate.

Where did all his money go, they are now asking in Manhattan’s Surrogates’ Court and New York Supreme Court.

Tony Bennett was getting at least $100,000 for each appearance in the 15 years before his last concert in 2022, lawyers for the sisters allege. His fee was far higher, they argue, for blockbuster shows like his two concerts with Lady Gaga at Radio City Music Hall in September 2016, a month before he signed the final family trust agreement.

The sisters’ lawyers estimate the singer earned at least $100 million in appearance fees from these performances. Yet the estate left to the four siblings is valued at under $7 million, the lawyers said last year. (That’s what remains of the $12 million after a $5 million widow’s inheritance mandated in the couple’s prenup.)

The Surrogate’s Court case demands a full accounting from the singer’s longtime business and personal manager, Danny Bennett, 71. The singer’s eldest child, Danny Bennett had sole power of attorney and was the family trust’s only trustee upon the singer’s death, in 2023, at age 96.

As part of that case, the sisters are also demanding all financial records for Danny Bennett’s 2022 sale of their father’s paintings, royalty streams, name-and-likeness rights, and memorabilia ranging from his Army dog tags to a signed Frank Sinatra photograph — “The Best g.d. pop singer I’ve ever heard!” Sinatra inscribed.

The sisters alleged last year that Danny Bennett paid himself more than $2 million in commission on the bulk sale, while giving them “a single modest distribution” of $245,000 each. The sisters “still do not have complete information about the transaction,” their lawyers alleged last year.

The sisters’ related March 2025 lawsuit in New York Supreme Court seeks a similar full accounting, plus an unspecified cash award and to have Danny Bennett removed as trustee due to his alleged “unlawful conduct.” The lawsuit also names younger brother Daegal and Susan Crow Bennett as defendants without alleging wrongdoing on their parts.

Danny Bennett has countered in court papers that his decisions were for the benefit of the family trust, that the sisters’ estimates of their father’s income and financial worth are grossly exaggerated, and that he has provided far more accounting than he was obligated to.

“He trusted me not to steal from him. And I did not,” Danny Bennett wrote in a February court filing. He declined to comment for this story, except through his attorney.

“This litigation only serves to distract from Tony Bennett’s illustrious and unprecedented success and legacy,” the attorney, Eve Rachel Markewich, told Business Insider.

“We have answered and addressed the specious allegations in court papers,” she said. “But rather than lending credence to them by commenting outside of the litigation context, our client prefers to concentrate on celebrations of Tony’s upcoming centennial in 2026.”

The beloved performer was born in 1926 in Queens, New York; he earned 20 Grammys and recorded 50 albums in the years since his first hit, “Because of You,” in 1951.

For “good and sufficient reasons”

The 2016 Bennett Family Trust Agreement specifically barred Johanna Bennett and Antonia Bennett from ever serving as trustees for the estate.

“Neither a daughter of the Grantor nor a descendant of a daughter of the Grantor may be appointed as a Trustee,” the trust agreement reads, with “grantor” referring to Tony Bennett. This was done “for good and sufficient reasons best known to the Grantor,” the trust agreement also reads, without elaborating.

Neither son was barred from being a trustee.

“Clearly,” Danny Bennett wrote in a February court filing, “Tony did not want his daughters to have any involvement, whatsoever, in his affairs or his business, during his life or after his death.”

Legal experts say such setups are not unusual. High-wealth, multi-heir families often create trusts that divide assets equally but limit decision-making, putting just one sibling in charge to avoid squabbling, said Mordy Mandel, a trust and estates attorney in New York City for 30 years.

Otherwise, “you have the other siblings always arguing, ‘How dare you sell that!'” said Mandel.

Parents commonly see different strengths in their children, assigning one child control over financial decisions, for example, and another over healthcare decisions, said Alan E. Sash, who handles trusts and estates at Bushell, Sovak, Kane & Sash in Manhattan.

Both attorneys have long experience with New York estate and trust law, and reviewed Tony Bennett’s final will and trust for this story. They confirmed that the documents limited Johanna and Antonia’s financial role to collecting their 25% bequests. They also said the sisters have every right to demand an accounting now.

“Danny had no legal obligation to tell his siblings how the trust was being managed,” Sash said. “But it may have been wise to do so along the way, so that there’s no surprises later on,” as is alleged to have happened here, he added.

Nothing but praise

Tony Bennett’s lawyer, Philip J. Michaels, who witnessed the singer’s 2016 signing of the final will and trust agreement, declined to comment on the estate battle or this story.

But the performer himself expressed nothing but confidence and gratitude toward his eldest son in the decades before Alzheimer’s took its toll.

“I love being managed by my son,” Tony Bennett told Billboard Magazine a quarter-century into their client-manager partnership, and at a time when he was selling out 100 dates a year.

“We get along great. Danny had me so set up, I could have retired five years ago,” the singer added in that 2006 interview. “But I’m still not finished with what I have to do.”

At awards ceremonies throughout the years, the singer called his son and manager to the stage to share credit, including for his comeback Grammy Award in 1995.

“Tony was unrelenting in his praise of Danny during his lifetime, and credited Danny with turning around his career after he hit bottom in the late 70s, including a near-fatal cocaine overdose and financial disaster that caused the IRS to try to seize his home in Los Angeles,” the son’s lawyers wrote in a court filing from November.

Both cases appear to be in their early days.

The Surrogate’s Court case, seeking only a thorough financial accounting, includes hundreds of pages of documents from the sisters’ original 2024 lawsuit against Danny Bennett. The paperwork from that lawsuit was transferred to the Surrogate’s Court in late July.

The 2025 lawsuit, meanwhile, may remain on ice until December 15, the deadline for Danny Bennett to file a response or an application to transfer that case, too, to Surrogate’s Court.

• Sam Dogen said the purchase of his current home brought him out of early retirement.
• Dogen suggests working longer during bull markets could have increased financial security.
• He advises testing living on a reduced income before retiring to plan for a smooth transition.

This as-told-to essay is based on a conversation with Sam Dogen, a 48-year-old early retiree, author, and stay-at-home dad based in San Francisco. It’s been edited for length and clarity.

I retired at 34 in 2012, and my wife retired a few years later at 35 in 2015. We’ve been mainly living off our passive income and investments since.

In 2023, I bought an expensive home I didn’t need, becoming house-rich and cash-poor. Buying this house affected our desired lifestyle in San Francisco. As a family of four with two children, we had less liquid or passive income, which made me feel quite uneasy.

In retrospect, retiring early was not the optimal career path. I’m 48 now, and if I were to talk to my 34-year-old self, I’d say stick it out for another five years and try to find a different work environment. Before anyone considers retiring early, I would suggest they speak to someone who has already done it and ask them what they would’ve done differently.

Working for 3 to 5 more years would have made more financial sense for me

Real estate and stocks were in a total bull market from 2012 to 2017. If I had worked longer, I probably would’ve been able to save and invest an extra $1 million. That decision could’ve generated $40,000 more in passive income at a 4% return rate, and I would maybe be more financially secure now.

Instead of retiring early, maybe I could’ve gone to a different office within the firm, like London or Hong Kong. Changing offices could’ve reset my experience, colleagues, restaurants, clients, and travel.

That would’ve probably enabled me to enjoy work more, and I would never have to wonder what it would’ve been like to work in Asia or Europe during my finance career.

The fear of not being able to properly care for my family in early retirement was pretty intense

I sold stock and treasury bonds to buy my new house. My passive income went from about $380,000 to $230,000, and I kept thinking about how I could regain that liquidity and passive income to feel more secure.

The fear was intense. It’s psychological, like a loss of identity or purpose. One of the biggest risks as an early retiree is that you can never get a job again. I kept that fear in check when I found a FinTech startup to join part-time at the end of 2023.

It felt great that after almost 12 years out of the workforce, I was able to jump back in, make money, and experience being in a community again. But after four months, I decided to quit and not look for another job.

I didn’t miss the unnecessary meetings, micromanagement, and office politics, and I was able to save around $10,000 a month from that to help replenish my lost income.

Having kids later in life, after retiring early, changed things

Maybe I’m technically poorer than before because I retired early, but soul-wise, I’m richer. The biggest benefit was being able to have children, because when I worked 60 hours a week and was so stressed, it was hard to even think about being able to afford or have children.

I really wanted to dedicate myself to being a full-time father for both my children during the first five years of their lives, and I was able to, but I realized that since I decided to have children afterward, the desire for money, status, and power for my children became huge.

People should be very calculated and aware if they decide to have children, and if they want to achieve Financial Independence Retire Early, also known as FIRE. It’s a really tough combination.

If you can’t live off of 50% of your paycheck for a year, you should keep working and saving

When I retired early, I tried to rely on investments and passive income to sustain my lifestyle. I always tell people who are considering early retirement to see how they could live on 50% or even 80% of their income for six months to a year.

The security of active income, retirement benefits, and health benefits will still remain, but this will show whether retirement is possible. If the desired lifestyle can’t be sustained, it’s probably necessary to save, invest, and work more.

There are so many resources, such as early retirement sites, podcasts, and books, that can help guide people who want to do this.

Set yourself up for success because it’s going to feel like a big transition

Instead of just giving two weeks’ notice and quitting, save right and get a good severance package. If you can do these two things, you will have a financial cushion to help you during your transition into early retirement, and you won’t rush back into the job market.

I’ve talked to people who retired early, and then three months later, they panicked and got a new job. After early retirement, people can experience a transition where they’re full of uncertainty and doubt about what they did. The life they knew for so long is no longer.

I tell my story on my blog, “Financial Samurai,” and in books I’ve written because it shows an example of taking that leap and things kind of working out.

Do you have a retirement story to share? Contact this reporter, Agnes Applegate, at aapplegate@businessinsider.com.

• MrBeast’s new CEO is reworking the YouTube star’s famous car giveaways.
• Beast Industries is entering a new phase of financial discipline.
• The company is renegotiating deals and looking to AI to reduce expenses.

MrBeast is known for extravagant giveaways, spending jaw-dropping figures to give away Teslas and even a Lamborghini in his YouTube videos. But the new CEO of his company, Beast Industries, is giving the practice a fresh look.

MrBeast previously paid retail prices for many products, including beverages, gym equipment, and dozens of Teslas. Under its new CEO, Jeffrey Housenbold, Beast Industries is seeking to get the products featured in videos for free or better, figuring lots of brands will gladly do so to appear alongside the world’s most famous YouTuber. The effort is being aided by an eight-person brand partnership team.

“My goal is to make everything we do profitable,” Housenbold told Business Insider in an interview.

Housenbold, who joined Beast Industries in May 2024 and became CEO in September, has been taking a broad look at Beast Industries’ finances. The company has also renegotiated ad contracts, increased ad rates, and sought to use AI to reduce costs where it can, a person familiar with the business said.

MrBeast built his online fame around his lavish videos that often blend spectacle and philanthropy. And he’s known to drop big chunks of cash to realize his creative vision.

“I lost tens of millions of dollars on that show,” he said on a podcast this year of his Amazon competition show, “Beast Games.”

The approach has helped make him the No. 1 star on YouTube, but it’s come at a high cost. Beast Industries lost money last year in large part due to massive spending on media, according to a leaked fundraising deck from early 2025 viewed by Business Insider.

Now that MrBeast has raised money from investors and has grown the company considerably, he’s adopting some more traditional business practices. The deck projected that these changes and other factors would make Beast Industries profitable this year. It’s unclear whether those estimates have changed since the deck’s creation.

The challenge for Housenbold and Team Beast is getting to profitability without killing the magic of MrBeast’s videos.

Read more about MrBeast’s overhaul of Beast Industries in our full deep dive