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Ex-Trump CFO Allen Weisselberg sentenced to five months in jail

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Allen Weisselberg, the longtime chief financial officer of Donald Trump’s real estate company, was sentenced to five months in jail for lying under oath in New York’s civil fraud case against the former president — Weisselberg’s second time behind bars.

The 76-year-old ex-CFO was sentenced Wednesday in New York state court under an agreement he reached with prosecutors when he pleaded guilty in March. His plea deal doesn’t require him to cooperate or to testify at Trump’s unrelated criminal trial over alleged falsification of financial records linked to hush money payments, which begins April 15. 

Weisselberg was taken into the state’s custody immediately after Judge Laurie Peterson imposed the sentence and is likely to serve his time at the Rikers Island jail complex, where he spent his last term on separate, tax-related charges. 

Allen Weisselberg, former CFO of Trump Organization, during sentencing in criminal court in New York
Allen Weisselberg, former chief financial officer of Trump Organization Inc., third right, at criminal court in New York

Curtis Means/Bloomberg

“Allen Weisselberg accepted responsibility for his conduct and now looks forward to the end of this life-altering experience and to returning to his family and his retirement,” his lawyer Seth Rosenberg said in a statement.

Weisselberg, who worked at the Trump Organization for decades before retiring in 2022, admitted falsely testifying about his role in the valuation of assets the state proved at trial had been inflated for years to get favorable terms on loans. He admitted to several incidents of perjury, both in depositions and in his testimony at trial. 

Trump’s triplex

He acknowledged lying in one deposition by denying his involvement in determining what numbers were used for valuing properties in Trump’s annual statement of financial condition. He also admitted lying under oath by claiming specifically that he had no role in determining the value of Trump’s three-story penthouse apartment, which was overvalued by about $200 million for several years.

“I never focused on the triplex, to be honest with you,” he said in his testimony when asked about his role.

Emails between Weisselberg and Forbes reporters who uncovered the overvaluation of the penthouse between 2012 and 2017 show the former executive “in fact paid close attention to the triplex,” Manhattan District Attorney Alvin Bragg’s office said in the plea agreement.

Before he struck his plea deal with Bragg’s office, Weisselberg was facing five counts of first-degree perjury, a felony punishable by as many as seven years in prison. In agreeing to the much shorter sentence, prosecutors said they took into account his age and willingness to admit wrongdoing. 

Tax case

Last year Weisselberg served 100 days of a five-month sentence after pleading guilty to tax fraud and other charges for accepting unreported perks like luxury housing and cars as salary. Under his first plea deal, he testified truthfully against Trump’s companies, which were convicted in 2022 of criminal tax fraud charges.

Wednesday’s sentence stems from a lawsuit filed by New York Attorney General Letitia James against Trump, his two oldest sons and Weisselberg. A judge found them all liable for fraud and issued a $454 million judgment against Trump, who is appealing. Weisselberg was hit with a $1 million penalty and barred from serving in a financial control function for any New York company.

Evidence at that trial showed that after Weisselberg retired, Trump paid him a $2 million severance package and continued to pay his legal bills.

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IRS Direct File reportedly ending next year

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The Trump administration is reportedly making plans to shut down the Internal Revenue Service’s Direct File free tax prep system next year.

The Associated Press reported Wednesday about the plans, which come amid widespread layoffs at the IRS. Elon Musk had posted on X in February that he had “deleted” 18F, a digital services team that helped build the Direct File system ahead of its initial pilot test last year. The IRS staff who had taken over development of the program were reportedly told last month to end their work on developing the system for next tax season. The U.S. Digital Service that also worked on developing Direct File has been renamed the U.S. DOGE Service after a takeover by Musk’s Department of Government Efficiency. 

Senate Finance Committee ranking member Ron Wyden, D-Oregon, blamed the move on lobbying by the tax prep software industry, as well as Treasury Secretary Scott Bessent.

“No one should have to pay huge fees just to file their taxes,” Wyden said in a statement Wednesday. “Direct File was a massive success, saving taxpayers millions in fees, saving them time and cutting out an unnecessary middleman that took money out of Americans’ pockets for no good reason,” Wyden said. “Trump and Secretary Bessent are robbing regular American families to pay back lobbyists that spend millions to make tax filing more expensive and more difficult.”

The Direct File system expanded from pilot tests in 12 states last year to 25 states this year, aided by the nonprofit group Code for America and its FileYourStateTaxes project.  A survey of over 1,000 Direct File and FileYourStateTaxes users reportedly found that 98% of respondents said they were either satisfied or very satisfied with the programs, according to the Federal News Network. Last year, former IRS commissioner Danny Werfel announced plans to make the Direct File program permanent, but the program has been repeatedly attacked by Republican lawmakers in Congress and the tax prep industry.

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S corporations bring tax advantages with caveats

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Electing to establish an S corporation could unlock the tax benefits enjoyed by millions of small business owners — as long as financial advisors and clients avoid some pitfalls.

Those include the ramifications of filing for deductions on the pass-through entity’s so-called qualified business income, the requirement of one single class of stock for the company’s equity and the implications of the S corp holding real estate, according to Tal Binder, CEO of Gelt. Binder’s firm works with high net worth clients and business owners through certified public accountants and artificial intelligence-powered tax services.

The caveats of S corp classification

For advisors and their clients, the S corp entity classification — named after Subchapter S of the Internal Revenue Code as a “Subchapter S corporation” or a “Small Business Corporation” — represents an opportunity with some tradeoffs. 

“Instead of thinking about it as just a tax structure, think about it as a tool — it’s a tool in the toolbox when you’re doing tax planning or tax strategy,” Binder said in an interview. “The S corp has a lot of tax benefits. It just becomes more complicated as you dig into the specifics and the numbers.”

Business owners and their advisors have likely run into those challenges in any number of situations — Binder noted that professional services firms such as a small wealth management company usually make the best candidates to be S corporations. The entity classifications of registered investment advisory firms affect industry M&A deals, and S corporations come in handy for clients who, for example, may be elite college athletes seeking tax savings on their “name, image and likeness” payments.

Most service-based businesses do elect to be S corporations, according to Miklos Ringbauer, the founder of Los Angeles-based tax firm MiklosCPA. However, state tax rules can alter the equation significantly, he noted, citing how California charges a flat annual duty of $800 per year for limited liability partnerships regardless of their profit, compared with a 1.5% rate on the net income generated by S corporations.

“You have to understand the state rules first — before you look at tax structure,” Ringbauer said in an interview. “Where we shine as tax professionals is providing that value, that guidance to the taxpayers, the investors to make the right choices, to help them to decide what is the best, optimized tax structure for their operation.”

READ MORE: 24 tax tips for self-employed clients

History to of S corporations

And tax pros have been doing so for decades.

Almost 70 years ago, small business owners gained the exemption from double taxation on corporate income flowing to their personal returns to the IRS, so long as they are domestic corporations, maintain a limited number and type of shareholders and have one class of stock. Today, there are about 5 million S corporations, according to the S Corporation Association, a business association and advocacy group. Before a recommendation by President Dwight Eisenhower’s Republican administration passed through Congress with the support of Harry Byrd, a Democrat from Virginia who was chairman of the Senate Finance Committee, small business owners faced “an oppressive level of tax,” a history on the group’s website stated.

“How significant was the creation of subchapter S?” it asked. “Consider that in 1958, the top income tax rate was 52% for corporations and 91% for individuals. That means dividends paid by a C-corporation to a high-income shareholder faced an effective tax rate of 96% Even a shareholder with median family income faced an effective federal tax of more than 60%.”

READ MORE: Business entities affect taxes and M&A — how RIAs weigh the choice

Potential downsides to S corp entities

The savings to the owners of S corporations add up in the right circumstances, but laws and individual tax implications could call for a sole proprietorship, partnership, limited liability company or a C corporation as a better fit.

In the case of a pass-through business tapping into the deduction for qualified business income that started with the Tax Cuts and Jobs Act in 2017, the S corporation could be a limiting factor based on the fact that the owner’s direct W-2 salary is likely to be lower in that situation, Binder noted. For some businesses that have a 401(k) or profit-sharing plan, the S corporation owners’ maximum tax-advantaged contribution can only rise to the level of their personal salary.

As another caveat to the S corporation, certain RIAs launch when advisors team up, but one of the advisors may bring a much more substantial base of clients to the business. That would suggest that one of the owners should have more control of the firm than the other, even if they each own half of the RIA, Binder said. They couldn’t set up the business that way as an S corporation that can only have one class of stock, though.  

“It doesn’t make sense, because you started it and built it for many, many years,” he said. “That might disqualify the S corp, so it’s not best in those cases.”

He brought up the additional problematic use of the structure with the idea of an S corporation RIA holding the building housing the business in the same entity, which is “the right approach” from the perspective of the general tax savings for real estate assets but “in the vast majority of cases not beneficial to you,” Binder said. The real estate could bring higher payments to Uncle Sam for an S corporation, based on the rules for tax basis and mortgage financing.

An LLC or LLP structure also provides more flexibility than an S corporation for transferring the real estate asset out of the business and into the client’s personal holdings without generating a taxable event, Ringbauer noted. From the perspective of a startup company that must take out heavy loans for capital expenses while incurring business losses in the first few years after launch, the S corporation could further cap the level of deductions — far below the amount available to an LLC or LLP, he said.

READ MORE: 25 tax tips for RIA M&A deals and other small business sales

Don’t go it alone on business-entity decisions

Unfortunately, many business owners attempt to choose their entity based on a simple online search or even a question to a public chatbot, according to Ringbauer.

“There’s a lot of incorrect information out there, which would result in incorrect guidance on how to treat stuff,” he said. “It’s a personal preference, but if it is properly guided, then the individuals who are starting the business will be able to make the right choice.”

In that vein, advisors who might otherwise avoid any mention of tax-related topics that fall outside their expertise should engage a local certified public accountant or enrolled agent “just to make sure that everything is correct” before the client fills out IRS Form 2553 electing to be treated as an S corporation, Binder said.

“I’d highly recommend the wealth manager to partner with a competent tax professional or CPA firm,” he said.

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FAF reports on standard-setting activity at FASB and GASB

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The Financial Accounting Foundation released its annual report Wednesday, offering an overview of its activities in 2024, especially at the two standard-setters it oversees, the Financial Accounting Standards Board and the Governmental Accounting Standards Board.

The report is available as both a downloadable PDF file and a digital, mobile-friendly version on the FAF website.

The report includes perspectives from leaders of the FAF, FASB and GASB, along with snapshots of how the teams keep stakeholders engaged. It also lists some of the highlights of 2024 FASB and GASB standards and exposure drafts on FASB projects such as recognition of intangibles and financial key performance indicators for business entities, as well as GASB exposure drafts on subsequent events and infrastructure assets. There’s also an update on the FAF’s strategic plan, plus a complete 2024 management’s discussion and analysis along with audited financial statements.

FAF executive director John Auchincloss and FAF chair Edward Bernard noted this will be their final annual report as Auchincloss will retire as FAF’s executive director in September, and  Bernard’s’s term as chair of the FAF board of trustees concludes in December. 

“When we assumed these roles, we inherited an organization that had a well-deserved reputation for excellence due to the experience, intelligence, and commitment of every single employee to our standard-setting mission,” they wrote. “We have been honored to serve in our roles and firmly believe in the organization’s bright future under new leadership.”

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