Reducing Capital Gains on a Highly Appreciated Portfolio

A planning framework for clients sitting on large embedded gains who would rather not write a 23.8 percent federal check

May 15, 2026

One of the most common conversations I have with clients in their fifties and sixties is some version of the same question. They have a position --- sometimes a single stock from a long-ago job, sometimes a fund they've owned for thirty years, sometimes the whole portfolio at once --- that has tripled or quintupled or more. They want to use the money, simplify the holdings, retire, fund a gift, buy a property. They also do not want to look at a tax bill that hands the federal government, the state, and the Medicare program a quarter or more of every appreciated dollar on the way out.

This is the right instinct. A highly appreciated portfolio is a good problem to have --- and it is also a problem that punishes naive selling. The dollar of gain that crosses the 20 percent long-term-capital-gains threshold, draws the 3.8 percent Net Investment Income Tax, and then gets stacked under a state long-term-capital-gain rate is a dollar that surrenders meaningful purchasing power for no portfolio benefit. The good news is that the planning side of the tax code gives an appreciated investor a surprising number of levers. They do not eliminate tax. They reshape it --- in timing, in rate, in vehicle, and sometimes in who pays it.

This piece walks through the levers I think about most often when a client comes in with a concentrated or broadly appreciated taxable portfolio. The tools are not exotic. They are tools the code has had on the books for years, and in some cases for decades. They just have to be coordinated, sized to the household's actual situation, and sequenced in the right order. As with every planning topic, the specifics belong in a conversation with your CPA, your estate attorney, and Perissos --- this memo is the framework, not the prescription.

Before talking about strategies to reduce capital-gains tax, it helps to know exactly what the tax actually is. For a married couple filing jointly in 2026, the federal long-term-capital-gains rate is zero on taxable income up to $98,900, fifteen percent from there to $613,700, and twenty percent on the portion above $613,700¹. For a single filer the corresponding breakpoints are $49,450 and $545,500¹. On top of that, the Net Investment Income Tax adds another 3.8 percent on the lesser of net investment income or modified adjusted gross income over $200,000 single / $250,000 joint². Those NIIT thresholds have been fixed since the tax took effect in 2013 and have never been indexed for inflation, which means more households drift into them each year purely from bracket creep².

At the top, that produces a 23.8 percent federal rate on every dollar of long-term capital gain a high-income couple recognizes. Add state tax. In a no-income-tax state the marginal rate stops there. In a high-tax state, the combined federal-plus-state long-term rate on a large realized gain can run from the high twenties into the mid-thirties. Figure 1 shows the federal rate ladder for a joint filer in 2026 and the points at which each transition happens.

Short-term gain --- a position held one year or less --- is even worse: it is taxed as ordinary income, which for a high-income household sits at 37 percent federal on top of the 3.8 percent NIIT and on top of any state. The single most reliable form of capital-gains reduction available to anyone is the one almost nobody thinks of as a strategy: hold the position past the one-year mark before recognizing. That single decision can move the rate on a $500,000 gain by twenty percentage points or more.

Once a position is long-term, the planning question splits along four different directions. You can avoid recognition entirely. You can recognize at a lower rate. You can convert the gain into a charitable deduction. Or you can defer recognition into a different year, vehicle, or owner. Most large appreciated portfolios use some combination of all four.

Figure 1: 2026 federal long-term-capital-gains marginal-rate ladder for married-filing-jointly couples. Rates step from 0% to 15% at $98,900 of taxable income, the 3.8% Net Investment Income Tax overlays beginning at $250,000 of MAGI, and the 20% federal rate applies above $613,700 of taxable income. Source: Rev. Proc. 2025-32; IRC Sec. 1411.

The simplest tool in the kit is also the most under-used. Under §1014 of the Internal Revenue Code, when an asset passes to an heir at the original owner's death, the heir's basis is reset to the asset's fair-market value at the date of death (or the alternate valuation date six months later, if the executor elects it)³. The unrealized gain that built up during the owner's lifetime is erased. The heir can sell the next morning and owe zero capital-gains tax on the entire pre-death appreciation³.

Step-up at death is the closest thing the tax code has to an eraser. For a household whose appreciated position is genuinely a "lifetime holding" --- meaning it is part of a position the family does not need to sell for cash-flow reasons --- the right tax strategy may simply be to not sell. Live off other resources (cash flow from other accounts, a securities-based line against the position itself, taxable-account basis recovery, Roth distributions, Social Security) and let the gain pass through the estate. The 2026 federal estate-tax basic exclusion is $15 million per individual after the One Big Beautiful Bill Act's permanent restructuring of §2010(c)(3)⁴, which means for most households below the federal exemption threshold, the only tax owed on the embedded gain is the income tax that would have been triggered by selling --- and that income tax is eliminated by §1014.

A few cautions are worth naming. State estate-tax thresholds in some states sit well below the federal exclusion, so residency matters. Inherited retirement accounts do not get a step-up under §1014 because they are treated as Income in Respect of a Decedent under §691 --- the eraser applies to the taxable account, not the IRA. And step-up is a strategy that works only if the position is not concentrated to the point of being a real risk to the household's standard of living during life --- holding a single stock to your eighties for tax reasons can produce a worse outcome than paying the tax. As a frame: step-up is a tool for the portion of an appreciated portfolio that the household genuinely does not need to liquidate. It is the wrong tool for the portion that funds retirement spending.

For positions the household is going to sell, the second lever is to make sure those gains are offset by realized losses to the maximum extent possible. Section 1211 lets a taxpayer use capital losses to offset capital gains without limit; once gains are fully absorbed, an additional $3,000 of loss can offset ordinary income each year, with the remainder carrying forward indefinitely. The wash-sale rule in §1091 limits the strategy --- if a "substantially identical" security is purchased within 30 days before or 30 days after the sale, the loss is disallowed⁵. The window is 61 days long in total (30 before, sale date, 30 after), and the disallowed loss is added to the basis of the replacement security rather than lost outright⁵.

Tax-loss harvesting matters more for highly appreciated portfolios than people realize. A diversified equity portfolio that is up materially in aggregate still contains individual positions, sectors, or factor exposures that are down. Those losses can be harvested without disturbing the overall market exposure of the portfolio by selling the down position and immediately buying a non-substantially-identical replacement --- a similar but not identical exposure --- to keep the desired market posture. Done year after year over a long market cycle, the harvested losses accumulate into a "loss bank" that can be deployed when a large gain needs to be realized.

This is the conceptual basis of what the industry has come to call direct indexing or tax-managed indexing. Rather than owning a broad index through a single fund, the portfolio holds the underlying constituents directly so individual lots can be harvested for losses while the overall portfolio tracks the index. The point of the structure is not the index exposure --- you could get that from any number of pooled vehicles. The point is that holding the constituents at the individual-lot level gives the household a steady stream of realized losses each year, which become carry-forwards available to offset gains in any future year. For a household that knows it is going to sell a large appreciated position three or five or ten years from now, building a loss bank in the years leading up to that sale can meaningfully cut the eventual tax bill. Figure 2 shows the arithmetic.

Two cautions. First, the wash-sale rule applies across all of a taxpayer's accounts, including a spouse's account and an IRA --- buying the substantially identical replacement inside a Roth or a 401(k) does not save the loss⁵. Second, harvesting losses inside a direct-indexed account permanently reduces the basis of the replacement position, which means the strategy doesn't make the gain go away --- it shifts the gain to a later year. The economic value comes from the time value of money and from the possibility that the later year will be a year you can absorb the gain at a lower rate or, ideally, at the §1014 step-up.

Figure 2: Illustrative cumulative loss bank generated by year-by-year tax-loss harvesting in a $2 million direct-indexed equity portfolio. Annual harvest yield varies with market volatility. These numbers are illustrative outputs of a simplified model --- not historical and not a forecast of any specific portfolio.

If a position has to be sold, the second-best outcome after not recognizing is to recognize at a low rate. The 2026 bracket structure described in the first section gives a couple two real planning bands. The 0 percent long-term-capital-gains bracket runs to $98,900 of taxable income joint¹. The 15 percent bracket runs from $98,900 to $613,700 joint, after which both the 20 percent federal rate and the 3.8 percent NIIT kick in^1,2. For a couple whose only income is the gain itself, the first $98,900 plus the standard deduction can come out essentially tax-free at the federal level, and the next half-million-plus is taxed at 15 percent before the 20 percent / NIIT threshold is hit.

That structure rewards multi-year sales. A retiree liquidating a $2 million embedded-gain position in one calendar year stacks the entire gain on top of any other income they happen to have that year and pays the top combined federal rate of 23.8 percent on most of it. The same retiree liquidating the same position over five years --- $400,000 of gain per year against a clean baseline of other income --- may keep the entire sale in the 15 percent bracket and avoid NIIT entirely. The math depends on the household's other income, the state, and the volatility of the underlying position, but the gap between "sell it all this year" and "sell it across five years" can run six or seven figures of total tax on a large concentrated position. Figure 3 illustrates the comparison.

There is also a useful window most households underuse: the years between retirement and the start of Social Security (or the start of RMDs at 73 or 75). In that gap, a couple often has very low ordinary income --- they are no longer working, but they have not yet turned on Social Security or required distributions. Those years are some of the cheapest in a lifetime to harvest long-term gains. The first roughly $130,000 of capital gains (the 0 percent bracket plus the standard deduction) can come out at zero federal rate. Coordinating partial Roth conversions and gain harvesting in those gap years is one of the highest-value planning windows in a working career, and it closes quietly once Social Security and RMDs begin.

A separate version of this strategy operates on the gift side rather than the sale side. The 2026 annual gift exclusion is $19,000 per donor per recipient⁴. A parent or grandparent who gives appreciated shares to an adult child in a lower bracket transfers the embedded gain along with the shares; when the recipient later sells, the gain is taxed at their rate, which for many adult children in the 0 percent or 15 percent long-term-capital-gain bracket is materially below the parent's rate. Gifts of appreciated shares to children under age 18 (or full-time students under age 24) run into the kiddie-tax rules of §1(g), which tax unearned income above a modest inflation-adjusted threshold (roughly the first few thousand dollars per year) at the parent's rate⁶, but for adult children the strategy can work cleanly. It transfers gain through the family at the recipient's bracket without any of the gift being taxable to the donor as long as it stays within the annual exclusion (or comes out of the donor's $15 million lifetime gift / estate exemption)⁴.

Figure 3: Federal tax on a $2 million long-term capital gain recognized in a single tax year vs. spread across five years at $400,000 of gain per year. Assumes joint filers, 2026 brackets, $20,000 of qualified dividends per year, the standard deduction, and no other ordinary income. Federal only --- state tax not modeled.

For households with a charitable intent, the most powerful capital-gains-reduction tool available is to give appreciated stock rather than cash. Under §170, a donor who contributes long-term-appreciated property to a qualified public charity may deduct the full fair-market value of the property on the donation date, subject to a 30 percent of adjusted-gross-income limit, with a five-year carryforward for any deduction not used in the first year⁷. Crucially, the donor recognizes zero capital gain on the transfer. The full appreciation passes to the charity untaxed, and the donor receives a deduction equal to fair-market value rather than basis⁷.

Compare two ways of giving $100,000 to a public charity. Path A: sell $100,000 of appreciated stock with a $20,000 basis, pay 23.8 percent federal on the $80,000 gain ($19,040), and send the after-tax proceeds to the charity. Path B: transfer the stock directly to the charity. The charity receives $100,000 in both cases (subject to size and liquidity). The donor in Path B keeps the $19,040 they would have paid in tax and takes a fair-market-value deduction of $100,000 against AGI rather than the $80,940 net of tax that Path A produced. The difference compounds across years for a household making annual charitable gifts. Figure 4 shows the arithmetic for a representative $250,000 annual gift.

For households whose charitable plans run multi-year, a donor-advised fund (DAF) extends the same logic. The donor transfers appreciated shares into the DAF in a single tax year, takes the fair-market-value deduction in that year (subject to the 30 percent of AGI limit for appreciated property), and then grants out to operating charities over time⁷. The deduction lands when the household needs it --- often in a high-income year (a business sale, a Roth conversion, a year of unusually large RMDs) --- while the grant-making happens at the household's preferred pace. The same five-year carryforward applies to any deduction beyond the AGI limit in the contribution year⁷.

For households with very large embedded gains and a meaningful charitable intent, a charitable remainder trust (CRT) is worth examining. A CRT is an irrevocable split-interest trust under §664 that pays the donor (or another non-charitable beneficiary) a stream of income for a term of years (up to 20) or for life, with the remainder passing to charity at the end of the term⁸. The annual payout must be at least five percent and no more than fifty percent of either the initial trust value (CRAT) or the annual trust value (CRUT), and the present value of the remainder interest going to charity must be at least 10 percent of the initial trust value⁸. The donor contributes appreciated stock, the trust sells it tax-free as a charitable entity, the trust then reinvests the proceeds in a diversified portfolio, and the donor receives both an upfront partial-FMV charitable deduction and an income stream over the term. For a household that wants to diversify a concentrated position, spread the recognition across decades rather than years, and ultimately benefit a charitable cause, the CRT is structurally elegant. It is also irrevocable, complex, and expensive to maintain --- it is not a small-portfolio tool.

Figure 4: Distribution of value when a $100,000 appreciated stock position ($20,000 basis, $80,000 long-term gain) is given to a public charity. Path A: sell stock, pay federal LTCG + NIIT at 23.8%, donate the after-tax proceeds. Path B: donate the stock directly. Charitable deduction available to the donor under Path B is $100,000 (FMV) vs. $80,960 (cash) under Path A.

Some appreciated portfolios are diversified to start with. Others are not. A position that began as a single-employer stock grant, an inherited holding, or a founder's stake can grow into half or more of a household's net worth before anyone really notices. Once concentration crosses that threshold, the planning conversation is no longer purely about taxes --- it is about risk. The reason the position is highly appreciated is also a hint that a meaningful share of the household's future is tied to a single ticker. A 50-percent drawdown in that name does not just hurt; it can change retirement.

The blunt solution is to sell, pay the tax, diversify, and move on. For a moderate concentration the math often supports that --- the tax is unpleasant but the risk reduction is worth it. For larger concentrations (or for households where the tax bill on a wholesale sale would itself be a planning event) several structures exist that reduce concentration without immediate recognition. Each comes with trade-offs and each has been used and abused in the marketplace, so they are not for every client.

Exchange funds --- specialized investment partnerships that pool together contributed concentrated stock from many investors and exchange the contributors into diversified partnership interests --- allow a holder of a single appreciated stock to gain diversified market exposure without recognizing the embedded gain at contribution⁹. The trade-off is illiquidity: the partnerships typically require a multi-year hold (commonly seven years) before tax-favorable redemption, and the eventual basis of the diversified portfolio inherits the contributor's original low basis. Exchange funds are not magic --- they defer recognition and reshape it, they do not eliminate it.

The Qualified Opportunity Zone (QOZ) program is a separate deferral mechanism. Under §1400Z-2, a taxpayer who recognizes a capital gain (from any source --- a sale of stock, a sale of a business, the gain leg of a divorce property division) can roll that gain into a Qualified Opportunity Fund (QOF) within 180 days of recognition and defer recognition while the investment is held¹⁰. The QOZ program was made permanent by the One Big Beautiful Bill Act in 2025, with the new decennial round of designations taking effect January 1, 2027¹⁰. For long-term holds, the program also offers favorable treatment on the appreciation that accrues inside the QOF itself, subject to the holding-period rules of §1400Z-2 as amended¹⁰. The QOZ structure was designed to channel patient capital into specific census tracts, so the underlying investments are typically real estate or operating businesses in designated communities --- it is a planning tool for households whose existing investment policy can accommodate that kind of exposure and whose horizon comfortably exceeds a decade.

For households with concentrated positions in publicly traded names who want immediate downside protection without selling, structured hedging strategies --- protective puts, costless collars, or longer-dated zero-premium structures --- can buy a floor of protection on the position without triggering recognition. These structures interact with the constructive-sale rules of §1259 and the straddle rules of §1092, both of which can disallow the deferral if the position is hedged too closely. They are useful, but they are an attorney-and-CPA conversation, not a do-it-yourself trade. The right time to evaluate them is well before a forced-liquidity event, not after.

Picture a couple, both 63, retiring at the end of 2026. They have an embedded long-term capital gain of $2 million inside a taxable account they want to draw down over their retirement. They live in a no-state-income-tax state, they have $20,000 a year in qualified dividends, and they have not yet started Social Security. They write annual charitable checks of roughly $40,000 to their church and a local nonprofit. They have two adult children, both in the 12 percent ordinary-income bracket.

The "naive" version of this plan sells the entire $2 million position next January to "get it over with." The gain stacks on top of $20,000 of qualified dividends. The 0 percent bracket up to $98,900 covers a sliver. The 15 percent bracket from $98,900 to $613,700 covers the middle. The portion above $613,700 is taxed at 20 percent and exposed to the 3.8 percent NIIT. The total federal tax on the $2 million gain runs into the low-to-mid $300,000s on a single-year sale.

A coordinated version of the same plan stretches the recognition across the gap years before Social Security and RMDs begin. The couple sells roughly $400,000 of gain per year for five years, keeping each year's gain almost entirely inside the 15 percent bracket and below the NIIT threshold. They use a donor-advised fund to contribute $100,000 of the most-appreciated lot in year one, taking the full $100,000 fair-market-value deduction against AGI in that year and pre-funding several years of $40,000 charitable grants out of the DAF in subsequent years⁷. They gift $19,000 of appreciated stock per child each December, transferring a slice of the gain to the children's 0 percent long-term-capital-gain bracket^1,4. Whatever remains in the taxable account when the surviving spouse eventually passes gets a step-up under §1014 and exits the family's tax balance sheet at zero embedded gain³.

The federal tax bill on the coordinated path can run thirty to fifty percent below the bill on the naive path, before the charitable deduction is even applied. None of the individual moves is exotic. They are the same tools that have been in the code for decades --- multi-year recognition under the rate structure, charitable deduction at fair-market value, gifting at the annual exclusion, step-up at death. The leverage comes from running them together rather than one at a time.

Planning around capital gains is the same way we approach every planning decision: long horizon, multi-year view, plan first and product second, tax-aware not tax-driven. We do not lead with a vehicle or a structure. We start with a picture of the household's bracket trajectory over the next five, ten, and twenty years, and we work backwards from where the family wants the portfolio to end up.

For most highly appreciated households we look at the question in roughly this order. First, what portion of the appreciated portfolio does the household genuinely need to liquidate during life, and what portion can simply pass through the estate under §1014? That answer alone resolves a meaningful share of the supposed "tax problem." Second, of the portion that must be sold, can the recognition be sequenced across the right years --- low-bracket gap years before Social Security and RMDs, years of unusually high deductions, years where a business sale or a charitable lump-sum opens a planning window? Third, is the household charitable enough that some portion of the gain is more efficiently routed through a donor-advised fund or, for a large enough situation, a charitable remainder trust? Fourth, does concentration risk require a structural solution --- an exchange fund, a QOZ rollover, a hedged structure --- to manage the position itself rather than just the tax on the position?

We do not run every household through every step. Most of the time, two or three of these levers carry almost all of the value, and the rest are either irrelevant to the family or net negative once complexity, cost, and irrevocability are weighed in. The point of having all four levers in mind is to know which two or three apply to this household, in this year, given this projected bracket path. The cost of getting that judgment wrong --- selling everything in one year, donating cash when you could have donated stock, harvesting losses in a year you don't need them, locking into an irrevocable structure for the wrong reasons --- is paid in tax dollars that don't come back. The cost of getting it right compounds quietly for decades.

As with every planning topic, the specifics belong in a conversation with your CPA, your estate attorney, and Perissos. The tax code has more flexibility on capital-gains recognition than most clients realize, and very little of that flexibility is captured in the default brokerage-statement model of "sell the lot, pay the bill, move on." A thirty-minute conversation about which lots, in which years, through which wrapper, can change the outcome materially.

A highly appreciated portfolio is a planning opportunity disguised as a tax problem. The dollar of gain that gets recognized at 23.8 percent federal in a high-income year is the same dollar of gain that, with planning, can be recognized at 0 percent in a low-bracket gap year, donated at fair-market value through a DAF, gifted to a lower-bracket child, deferred through an exchange fund, or erased entirely at step-up. The tools are not exotic. They have been in the code for decades. They simply require a household to think in years rather than days, and to coordinate the sale calendar, the charitable calendar, the gifting calendar, and the estate plan as one document rather than four.

The instinct to "just pay it and move on" is understandable. For modest gains and households with strong other income, it is sometimes the right answer. For households with seven-figure embedded gains, concentrated positions, or charitable intent, it is almost always leaving meaningful money on the table. The right framework starts from what the household actually wants to do with the money --- spend it, gift it, give it, leave it --- and works backward through the rate structure, the deduction structure, the estate structure, and the gap years before forced-income events begin.

I am happy to sit down with any household that wants to map this picture out. The first conversation is usually not about products or structures. It is about the family's actual five-year plan, written down in one place. From there, the right tax levers tend to choose themselves.

All my best,

Brandon VanLandingham, CFA, CMT, CFP

Founder / CIO

¹ Rev. Proc. 2025-32, 2026 inflation-adjusted long-term capital-gains rate breakpoints (0%, 15%, 20% thresholds for joint, single, head of household, MFS, and trusts). IRS, https://www.irs.gov/pub/irs-drop/rp-25-32.pdf.

² IRC §1411 (Net Investment Income Tax); IRS Topic No. 559, Net Investment Income Tax, https://www.irs.gov/taxtopics/tc559; IRS, Questions and Answers on the Net Investment Income Tax, https://www.irs.gov/newsroom/questions-and-answers-on-the-net-investment-income-tax.

³ IRC §1014 (basis of property acquired from a decedent); IRS Publication 551, Basis of Assets, https://www.irs.gov/publications/p551.

⁴ IRC §2010(c)(3) as amended by the One Big Beautiful Bill Act of 2025, Pub. L. 119-21 (basic exclusion amount of $15 million per individual for 2026); IRS Newsroom, IRS releases tax inflation adjustments for tax year 2026, including amendments from the One, Big, Beautiful Bill, https://www.irs.gov/newsroom/irs-releases-tax-inflation-adjustments-for-tax-year-2026-including-amendments-from-the-one-big-beautiful-bill (annual gift exclusion $19,000 for 2026).

⁵ IRC §1091 (loss from wash sales); IRS Publication 550 (2025), Investment Income and Expenses, https://www.irs.gov/publications/p550.

⁶ IRC §1(g) (tax on unearned income of certain children); IRS Topic No. 553, Tax on a child's investment and other unearned income (kiddie tax), https://www.irs.gov/taxtopics/tc553; IRS Instructions for Form 8615.

⁷ IRC §170 (charitable, etc., contributions and gifts); IRS Publication 526, Charitable Contributions, https://www.irs.gov/publications/p526 (30% of AGI limit for long-term capital-gain property contributed to public charities; five-year carryforward).

⁸ IRC §664 (charitable remainder trusts); Rev. Rul. 2008-41 and related guidance, https://www.irs.gov/pub/irs-drop/rr-08-41.pdf; IRS, Charitable remainder trusts, https://www.irs.gov/charities-non-profits/charitable-remainder-trusts (5% minimum / 50% maximum payout; 10% minimum remainder).

⁹ IRC §721(b) and §351(e) (transfer-to-investment-company rules, including their application to partnership-form "exchange funds"); Rev. Rul. 2003-51, https://www.irs.gov/pub/irs-drop/rr-03-51.pdf.

¹⁰ IRC §1400Z-2 (Opportunity Zone deferral and exclusion provisions), as amended by the One Big Beautiful Bill Act of 2025; IRS Newsroom, Treasury, IRS provide guidance to States for nominating census tracts as qualified opportunity zones under the One, Big, Beautiful Bill, https://www.irs.gov/newsroom/treasury-irs-provide-guidance-to-states-for-nominating-census-tracts-as-qualified-opportunity-zones-under-the-one-big-beautiful-bill.

This piece is educational. It is not legal, tax, or accounting advice and is not a recommendation to take or refrain from any specific action. Tax law is fact-specific and changes regularly. Please coordinate any decisions discussed here with your attorney, your CPA, and Perissos before acting.

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