The US Treasury Department has expressed concern over a number of high-profile tax strategies touted by Wall Street that it says may be “too good to be true.”
Officials told an industry gathering on Tuesday morning in New York the department considers that some of these products may be abusive, and said it is actively evaluating the tools available to address them.
However, they stopped short of announcing new guidelines, saying instead they “expect a serious dialogue with the market before positions harden” and investors are placed at more risk.
The strategies under scrutiny include so-called 351 conversions, box-spread exchange-traded funds, products that offset ordinary income, and funds that avoid dividend income by flipping between other ETFs. Speaking at a Wall Street Tax Association seminar, Kevin Salinger, deputy assistant secretary for tax policy at the Treasury, and Erika Nijenhuis, senior counsel, said the department has no wish to over-engineer rules, but it cannot ignore a market developing around transactions with results Congress did not appear to intend.
“We’re not here to be over-broad or disruptive, but we are also not prepared to turn the blind eye to aggressive planning,” Salinger said. “We do not want to act in a way that rewards taxpayers or promoters who have crossed lines that should not be crossed and disadvantages taxpayers who have stayed within the lines.”
The comments come amid a boom in transactions and products that help wealthy American investors reduce or delay the taxes they owe. Known as tax alpha strategies, they largely deploy financial engineering to take advantage of various rules in the US tax code. They are chiefly focused on capital gains, though a few specialized products have even managed to offset regular income.
The Treasury has previously voiced concern over the growing use of 351s, which involve converting a portfolio of assets into an ETF to rebalance without realizing a capital gain. But Salinger and Nijenhuis made it clear that officials have a much broader focus.
Funds that generate ordinary losses are among the more controversial in the tax-aware industry, since they aim at wiping out income subject to the highest tax rates, including wages. They’re epitomized by the AQR TA Delphi Plus Fund, which had $6.6 billion as of June 30 and last year recorded ordinary losses equal to 28% of capital invested, according to documents seen by Bloomberg News.
“We have seen pitch decks where they advertise that if you invest a million dollars, you may get a $300,000 ordinary loss,” Salinger said, without naming any products or money managers. “I would advise investors to be cautious when something looks too good to be true because it probably is.”
Delphi Plus generates losses by taking advantage of the tax rules for notional principal contracts, the legal term for swaps. In a swap, the payments are ordinary in nature, which means ordinary losses arise whenever an investor has to pay their counterparty for a losing bet. But when a position is terminated early, it can be booked as either a capital gain or loss.
At the seminar, the two Treasury officials raised concerns over the way NPCs can be used to selectively create ordinary losses and capital gains for similar economic transactions. They also discussed other methods that give rise to ordinary deductions, including so-called identified straddles and a rule that lets a trader elect whether a foreign-currency derivative position should receive ordinary or capital treatment.
Salinger and Nijenhuis also covered various ways the rebalancing mechanism of ETFs — which enables them to offload appreciated assets without incurring capital gains — can be used to avoid taxes. While such in-kind transactions alone are not a problem, they can be combined with other steps to produce a result that appears “inconsistent with what Congress intended,” Salinger said.
He specifically mentioned 351 conversions where the redemption mechanism is used to dispose of appreciated securities which are then replaced with positions that fit in the product’s intended strategy. He also homed in on deals where stocks are first contributed to an exchange fund, which then conducts the ETF conversion.
When asked about possibly labeling 351 exchanges as “transactions of interest” — a designation for deals with tax-avoidance potential that would require additional disclosure — Salinger said “all the tools are under consideration for all of the transactions that we’re going to talk about today.”
The two officials also discussed ETFs that trade in and out of other ETFs in order to avoid dividend distributions, as well as box-spread ETFs.
The largest of the latter is the $13 billion Alpha Architect 1-3 Month Box ETF, which uses option trades to generate returns similar to Treasury bills that are taxed as capital gains on the ETF, rather than interest income.
Isn’t that rich? This cortupt admin and the other 535 politicians inside trade everyday and thumb their nose at us, but the FED IS concerned that us everyday Americans are overreaching current legal tax break strategies.
100% correct. Maybe the Treasury should be asking how Trump was able to make $1.4 billion on his meme coin while investors in that coin lost $3 billion+.
They should get rid of real estate 1031, bonus depreciation and REPS. Millions of Americans, including many high income W2 earners married to those who file as REPS to avoid taxes the rest of us have to pay.
Facts Only
* The US Treasury Department expressed concern over high-profile tax strategies touted by Wall Street, suggesting they may be "too good to be true."
* Officials stated the department considers some products potentially abusive and is evaluating tools to address them.
* Strategies under scrutiny include 351 conversions, box-spread exchange-traded funds, products offsetting ordinary income, and funds avoiding dividend income by flipping between ETFs.
* Kevin Salinger and Erika Nijenhuis indicated a desire to avoid over-engineering rules but cannot ignore market development around transactions with unintended legislative outcomes.
* The Treasury has previously voiced concern over the growing use of 351s involving portfolio conversions without realizing capital gains.
* Funds generating ordinary losses are controversial because they aim to wipe out income subject to high tax rates, including wages.
* One specific product example noted is the AQR TA Delphi Plus Fund, which reportedly recorded ordinary losses equal to 28% of capital invested in one year.
* Losses can arise from notional principal contracts (swaps) where early termination results in capital gains or losses.
* The rebalancing mechanism of ETFs was discussed as a method that can be used to avoid taxes when combined with other steps.
Executive Summary
The US Treasury Department has expressed concern regarding certain high-profile tax strategies promoted by Wall Street, suggesting they may be overly aggressive. Officials indicated that some of these products might be abusive and are actively evaluating tools to address them. The department stated it does not intend to create overly broad rules but is also unwilling to ignore market developments concerning transactions Congress did not explicitly intend. Specific strategies under review include 351 conversions, box-spread ETFs, products designed to offset ordinary income, and funds avoiding dividend income through ETF flipping.
Treasury officials emphasized a need for dialogue with the market before finalizing guidelines, noting that current positions place investors at greater risk. Concerns were raised regarding investment vehicles that generate ordinary losses, such as certain fund structures, where investors claim potential ordinary losses based on swap rules and early termination of contracts. The department also reviewed mechanisms like the rebalancing features within ETFs and methods involving 351 conversions to determine if they align with legislative intent.
Full Take
The narrative frames the tension between aggressive financial engineering strategies and the intent of the legislative process, positioning regulatory intervention against self-serving market activity. The central conflict is not simply about legality but about the alignment of complex transactions—like 351s or ETF rebalancing—with intended tax policy. The framing leverages an appeal to fairness: that entities benefiting from these structures are operating outside the intended boundaries set by Congress, suggesting a systemic mismatch between economic reality and regulatory structure.
A key pattern is the use of specific, high-leverage financial terms (like "tax alpha strategies," "351 conversions," and "ordinary losses") to create an impression of specialized knowledge that the regulator must catch up to, which simultaneously creates a sense of urgency for disclosure while diffusing clear action. The juxtaposition of official, cautious regulatory dialogue with the highly charged, accusatory commentary regarding wealth concentration highlights a gap between governmental oversight and the perceived scope of private financial maneuvering.
The implication is that true cognitive sovereignty requires understanding not just the technical mechanics of tax code evasion, but also the systemic reasons—the historical or political context—behind legislative structures. The narrative invites an inquiry into who defines "reasonable" tax planning and whether regulatory efforts adequately capture these evolving, complex strategies, particularly when addressing wealth accumulation versus broad public tax obligations.
Bridge Questions: What frameworks exist to assess whether financial engineering aligns with congressional intent, even in the absence of explicit rules? How can regulatory bodies effectively monitor and address novel transactions that evolve rapidly outside established legal definitions? What are the long-term societal implications when market incentives drive outcomes that diverge significantly from stated political goals?
Sentinel — Human
The article presents factual elements regarding Treasury concerns about tax strategies but concludes with highly biased and unsubstantiated political commentary, suggesting a composite or heavily edited piece.
