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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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Senate Republicans release revised tax cuts and debt limit bill

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Senate Republicans propose to cut trillions of dollars in taxes for households and businesses in their version of President Donald Trump’s signature economic package, a plan that comes at the expense of curbing health coverage for some low-income Americans and adding to US deficits.

The bill would preserve Trump’s first-term tax cuts and create several new breaks that he championed on the campaign trail — including eliminating taxes on tips. To offset the cost, senators are proposing to repeal some clean energy tax credits and scale back Medicaid benefits spending more deeply than in the House-passed bill.

Within hours of the bill’s release, cracks were forming among Republicans about the scope of the Medicaid cuts. 

“This bill needs a lot of work,” Senator Josh Hawley, a Missouri Republican, told reporters Monday. “This will close hospitals in rural America.”

Republicans can only afford to lose three votes in the Senate, putting pressure on GOP leaders to broker compromises to push Trump’s agenda through the chamber.

The bill expands some tax breaks while raising the debt ceiling by $5 trillion, instead of $4 trillion in the House-passed measure. It largely hews to the House bill as Senate GOP leaders aim to avoid a protracted negotiation on the substance of the legislation that could risk the U.S. defaulting on a payment obligation when the Treasury Department can no longer employ extraordinary debt limit measures, as soon as mid-August. 

Notably absent from the bill is a deal on the state and local tax deduction, one of the most contentious issues facing lawmakers in the negotiations. The draft includes the current $10,000 SALT cap as a placeholder while lawmakers continue to debate the politically important writeoff.

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H.R.1, Senate Finance Committee

“We understand that it’s a negotiation,” Senate Majority Leader John Thune told reporters on Monday. “Obviously, there had to be some marker. We are prepared to have discussions with our colleagues here in the Senate and figure out a landing spot.”

Thune added that his chamber plans to vote on the bill next week in order to meet a July 4 deadline to send the legislation to Trump.

Finance Committee Chairman Mike Crapo and other Senate Republicans have pushed to reduce the $40,000 cap included in the House version. House lawmakers representing high-tax states have threatened to block the measure if the cap is lowered. Current law allows only a $10,000 cap for individuals and couples, though the limit is set to expire at the end of the year. 

The committee draft’s biggest change is making permanent three business tax breaks that in the House version expire after 2029. That includes the research and development deduction, a provision expanding debt interest writeoffs and expensing for new equipment, including most machinery and factories. The interest expensing changes benefit banks, while research-heavy sectors like pharmaceuticals and information technology should benefit from the longer research and development break.

However, the bill pared back a House proposal to increase a business deduction for closely held businesses to 23% from 20%. The Senate plan makes permanent the current 20% write-off that is set to expire at the end of the year.

Democrats were quick to criticize the legislation, saying that it skews benefits to wealthy individuals and business owners.

“This is textbook class warfare,” Senator Ron Wyden of Oregon, the top Democrat on the Senate Finance Committee, said. “It is caviar over kids.”

The bill also scales back a proposed tax on university endowments. The House bill called for a top rate of 21% on the wealthiest universities, but the Senate’s draft tops out at 8%. The legislation also omits a House proposal that would impose taxes on large private foundations, such as the Gates Foundation.

Trump’s plan

The legislation largely renews Trump’s 2017 tax cuts for households and small businesses, which are set to expire at the end of 2025. The bill also includes a new slate of levy reductions, including some of the president’s campaign trail promises to eliminate taxes on tips and overtime pay.

The plan proposes cuts to the Medicaid program for low-income and disabled people that are more aggressive than policies the House passed. The Senate went further than the House’s proposal to limit the options states have to fund their share of Medicaid. The House bill would set a moratorium on new or increased taxes on medical providers, while the draft Senate bill would cut the amount that states that have not expanded Medicaid under the Affordable Care Act can tax health care providers to help fund their Medicaid programs.

The Medicaid reductions have been politically divisive even within the Republican Party, with some senators warning that the cuts could harm their constituents. 

The legislation augments the House version of the child tax credit, making permanent a $2,200 per-child credit. The House bill called for a $2,500 tax break, but the measure was only temporary. The bill would create a new $6,000 deduction for older people and establishes a new deduction for charitable donations for people who don’t itemize their tax returns.

Energy credits

The bill would also end the $7,500 tax credit for electric vehicles within 180 days of the legislation being enacted. The draft also calls for an end for subsidies to wind and solar.

The draft ends a credit for companies, including Sunrun Inc., that lease rooftop solar systems as well as homeowners who buy them outright. The elimination of the credits would decimate the already reeling solar industry, with the uncertainty of the fate of the clean energy incentives already causing disruption in the market.

Despite a lack of agreement on several key policy issues, the Senate intends to pass the legislation on an ambitious timeline. Republicans are aiming to pass the bill out of the Senate and send it back to the House for final approval by July 4. Trump has put pressure on lawmakers to coalesce around the legislation, which we has dubbed the “One Big, Beautiful Bill” and will serve as the centerpiece of his legislative agenda.

The release of the Senate bill comes as Trump’s allies have started a messaging campaign to defend his first-term tax cuts. Changes to the corporate tax code that Trump pushed through in 2017 spurred companies to invest for years, according to a new academic study from Kevin Hassett, head of the White House’s National Economic Council.

The analysis found that a one percentage point decrease in the user cost of capital drove between a 1.68 and 3.05 percentage point increase in the rate of investment.

Other economists caution that Trump’s planned tax cuts will add pressure to the government’s already surging deficit and keep borrowing costs elevated, for both business and households.

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Tax savings for business owners hiring kids

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Business owners who employ their children in a reasonable but limited capacity at their firms can rake in tax savings and start their kids’ first retirement accounts in the process.

But the entrepreneurs and their financial advisors or tax professionals must ensure they’re diligently keeping the kids’ employment records, complying with some variation in state-level rules for business entities and addressing any other potential ramifications, according to Miklos Ringbauer, of Los Angeles-based MiklosCPA, and Kevin Thompson, CEO of Fort Worth, Texas-based RIA firm 9i Capital Group.

READ MORE: 24 tax tips for self-employed clients

Key benefits of hiring your child

For instance, Ringbauer usually advises clients to restrict their compensation for any summer jobs or other employment for their children to less than $15,000. That’s the standard deduction for 2025, the highest amount of income that, in most cases, doesn’t carry the requirement to file a return. 

In turn, the business may deduct the wages as an expense and often avoid Social Security, Medicare, Federal Insurance Contributions Act (FICA) and Federal Unemployment Tax Act (FUTA) taxes, as well as estate and gift duties. 

And the child acquires some invaluable lessons about a day’s work, alongside potential investments such as a Uniform Transfers to Minors Act (UTMA) portfolio with a parent as the custodian or a Roth or traditional individual retirement account. But the benefits won’t accrue from brazen attempts by parents to give their kids money.

“There’s an incredible wealth of information out there and options a business owner and their children can take advantage of legally to help reduce taxes on the parents’ side,” Ringbauer said. “This could be an incredible wealth transfer, if it is done right and done appropriately.”

For advisors and their clients, that entails using the same payroll records as they do for any other employees and assigning the kids to perform actual work aligning with their hours and skills. And, of course, they need to “be careful” that they’re not running afoul of guidelines for child labor or the so-called kiddie tax on unearned income or investments, Thompson noted.

“You can’t pay your kid $15,000 over the summer for raking leaves. It has to be reasonable compensation, and you have to have them in your system,” he said. “Having the IRS come into your place just because you paid your kid some money over the summer is not a good look.”

READ MORE: The basics of S corporations — and the pitfalls for small businesses

Helpful lessons

Whether they’re working for their parents or another employer, a summer job can introduce young people to concepts such as the difference between an independent contractor and a W-2 employee and any wittholdings from their paycheck, according a recent guide to IRS rules for teens by Jill Kenady, a tax materials specialist with the University of Illinois Tax School. Documents like a tax checklist compiled by the school, and IRS releases for students and summer employees could aid parents and youngsters navigating the rules, Kenady wrote.

“Summertime is near, which means teens will start jobs, which is the initiation into adulthood,” she wrote. “These jobs offer a sense of independence along with a wonderful way to earn their own money. However, with great earnings come significant responsibilities, specifically tax responsibilities. It is your job as a tax practitioner to help teens and their parents navigate the tax laws and the impact of summer employment.”

The advantages to parents who employ their kids can pile up so high that Ringbauer said he begins speaking with business owners about the possibilities shortly after the child is born. As long as they comply with the rules, a pediatrician or a child dentist could consider hiring their kid to act as a model for advertisements or pictures on the website for the small business, he noted.

On the other hand, Ringbauer stressed that it’s important for the parents to talk through their ideas with an advisor or tax pro before putting anything in motion. The entity classifications of a business and independent contractor or W-2 employee status for the child could bring more complexity to their decisions. Then there are the more basic concerns about any potential for accidents on the job or the challenges of a parent working in the same office as their child.

READ MORE: 3 tax strategies for summer daycare, jobs and vacation rentals

Keep implications in mind

Among prospective clients, the most common problem is that it can look like a business owner is trying to simply transfer money to their child “without actual work or suitable work,” Ringbauer said.

“Eventually, they didn’t turn into my client, because they didn’t like the answers I gave them,” he said, recalling one business owner who was trying to skirt the rules. “After-the-fact errors are the biggest pitfalls, and it’s across the board.”

However, the array of potential strategies for small business owners provide “limitless reasons and opportunities to do it right, and the benefits significantly outweigh the immediate gratification of savings in dollars,” Ringbauer added.

The incentives explain why the method “makes a lot of sense” for many business owners and kids who could open their own retirement accounts, Thompson said. But there are some caveats. For example, those assets could affect possible financial aid for college or other benefit programs that take net worth into account.

“We have to look at the implications on them saving dollars under their own names,” Thompson said. “I have to be careful, because if they have too much money under their name it could ruin their benefits.”

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One Big Beautiful Tax Bill full of impactful provisions

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The One Big Beautiful Tax Bill Act, as passed by the House and revised text was released Monday by the Senate, includes a number of significant tax provisions for both corporate taxpayers and nonprofits.

“Even before we saw the legislative text of the One Big, Beautiful Bill, we knew these would be the big provisions for most of our clients that they were interested to see what was going to happen,” said Jess LeDonne, director of tax technical at the Bonadio Group. “The big one that I get the most questions about right now would be the expensing of research and development costs, Section 174. That provision, specifically, allows for the temporary suspension of the amortization, so you would be able to immediately expense those costs. They also expanded that provision to include software development expenditures as well. Some of the provisions are kind of a permanent extension of some of the Tax Cuts and Jobs Act. This one specifically is a temporary suspension of the amortization requirement. Essentially it will allow for immediate expensing of R&D costs only for tax years 2025 through 2029. This isn’t permanent, but it still is for a lot of clients a welcome potential change.”

Another significant provision involves bonus depreciation, Section 168(k). “The bill, as written as it currently sits in the Senate, would allow for 100% bonus depreciation to be reinstated,” said LeDonne. “This would again be temporary, based on the placement service date of the equipment, and it would be for a property placed in service from essentially Inauguration Day. They picked Jan. 19 of this year, and before Jan. 1, 2030.”

She sees that as a welcome extension. “That was the one we have been watching phase down already, and was set to phase out completely by 2027,” said LeDonne. 

Another provision involves the qualified business interest deduction provision. “There’s an increase there from 20% to 23% and that one does not have a sunset date, so that would be more of a permanent potential increase to that QBI deduction,” said LeDonne. 

Business interest deductions would also be extended “The last one that I’m always being asked about would be the change in the calculation for the limitation on business interest expense deductions in 163(j),” said LeDonne. “There’s a temporary reinstatement in the bill to go back to the EBITDA-based calculation. And that would be for tax years 2025 through 2029. That was the other one that we’ve been watching those specific provisions to see what’s going to happen based on the Tax Cuts and Jobs Act expirations and phasedowns. Those were some of the biggest business-side provisions that we’ve been asked about.”

Nonprofit tax changes

Nonprofits such as foundations, colleges and universities would also see wide-ranging impacts from the bill that was passed by the House and whose amended text was released Monday from Senate Republicans.

“The tax bill, as it’s written right now out of the House, has a number of provisions that impact the nonprofit sector,” said Aaron Fox, a managing director at CBIZ. “We will see how many of them stay in effect after the Senate is done marking up the bill. Some of the more notable provisions in the bill, to my mind, are the private foundation increase in tax rates depending on the size of their asset base. That would mark a significant departure from historic norms, where previously the tax rate was only 1.39%, and the rationale was that it was there to pay for the cost of administering foundations. But the increased rates up to 10% for the very large foundations with $5 billion or more in assets really represents a change in approach and would pay for other parts of the bill.”

The increase in tax on investment income for colleges and universities could also have a major effect on larger educational institutions. “Right now, the current rate is 1.4%, but in certain instances where the student-adjusted endowment amount goes up to $2 million or more, then colleges could be looking at significant increases in that excise tax rate,” said Fox. “That’s a pretty significant one that would not impact all of higher education, but have a pretty broad impact on the bigger colleges that have very strong balance sheets.”

Other provisions involve royalty income and transportation tax fringe benefits. 

“Royalty income change is going to be pretty broad in application, because many nonprofits, especially in the social welfare space, have royalty contract arrangements, and some of those royalties relate to name and logo licensing or sales,” said Fox. “I think that has an opportunity to have a really broad impact as well. Finally, my fourth one would be what they’re thinking about doing with transportation tax benefits and bringing back the rule that created unrelated business income tax on the provision of those benefits, which is sort of a tricky area in the tax law. It created a lot of uncertainty and difficult filings for nonprofits back in 2017 and 2018 when this idea was first put into law and then later repealed.”

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