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Capital gains taxation sits at the heart of tax planning strategy, and you'll be tested on your ability to distinguish between rate structures, holding period requirements, and special asset categories. The exam expects you to understand not just what the rates are, but why Congress created preferential rates for certain types of gains—encouraging long-term investment, supporting small businesses, and recapturing prior tax benefits like depreciation deductions.
The key concepts here include holding period distinctions, preferential rate structures, recapture provisions, and income-based phase-ins. Don't just memorize that long-term gains get better rates—know which assets qualify, what thresholds trigger higher rates, and how special provisions like QSBS exclusions and Section 1250 recapture interact with the basic framework. When you see a fact pattern on the exam, you're being asked to apply the right rate to the right gain.
The fundamental distinction in capital gains taxation is the holding period. Congress intentionally rewards patient investors with lower rates, creating a two-tier system that drives most tax planning decisions around the timing of asset sales.
Compare: Short-term vs. long-term gains—both are capital gains, but the rate difference can exceed 17 percentage points (37% vs. 20%). If an FRQ presents a taxpayer considering selling an appreciated asset, always check whether waiting a few more days crosses the one-year threshold.
Beyond the basic rate structure, high-income taxpayers face an additional layer of taxation designed to fund healthcare programs. Understanding when NIIT applies is essential for calculating total tax liability on investment income.
Compare: A taxpayer in the 20% long-term capital gains bracket with MAGI above the NIIT threshold pays an effective 23.8% rate, while a taxpayer just below the threshold pays only 20%. This cliff effect makes income management around these thresholds a key planning consideration.
Not all long-term capital gains receive the standard preferential rates. Certain asset categories carry higher maximum rates, either because of recapture provisions or the nature of the asset itself.
Compare: Collectibles (28% max) vs. Section 1250 recapture (25% max)—both exceed standard long-term rates, but for different policy reasons. Collectibles don't generate depreciation deductions, so the higher rate reflects a policy choice to limit tax benefits on "non-productive" assets. Section 1250 recapture exists because the taxpayer already received a tax benefit from depreciation.
Congress has created several provisions that go beyond reduced rates to offer partial or complete exclusion of capital gains, typically to encourage specific economic behaviors like small business investment or real estate reinvestment.
Compare: QSBS exclusion vs. Section 1031 exchange—QSBS can permanently exclude gain, while 1031 only defers it (basis carries over to replacement property). However, 1031 has no dollar cap and can be used repeatedly, making it powerful for real estate investors building wealth over time.
Qualified dividends receive the same preferential rates as long-term capital gains, blurring the line between these two income categories for tax purposes.
Compare: Qualified dividends vs. long-term capital gains—same rates, but different holding period tests. Capital gains require holding the asset more than one year; qualified dividends require only 61 days around the ex-dividend date. Non-qualified dividends lose preferential treatment entirely and are taxed as ordinary income.
Federal rates tell only part of the story. State taxation can significantly impact total tax liability on capital gains, and the treatment varies widely across jurisdictions.
| Concept | Key Rates/Rules |
|---|---|
| Short-term gains | Ordinary income rates (10%–37%), assets held ≤1 year |
| Long-term gains | 0%, 15%, or 20% based on income; held >1 year |
| Net Investment Income Tax | Additional 3.8% above MAGI thresholds |
| Collectibles | 28% maximum rate |
| Section 1250 recapture | 25% maximum rate on depreciation recapture |
| QSBS exclusion | Up to 100% exclusion if held >5 years |
| Qualified dividends | Same rates as long-term gains (0%, 15%, 20%) |
| Section 1031 exchanges | Complete deferral on like-kind real property |
A taxpayer sells stock held for exactly 365 days at a gain. Is this gain taxed at short-term or long-term rates, and why does the specific day count matter?
Compare the tax treatment of a gain on collectible coins versus a gain on publicly traded stock, assuming both were held for three years by a high-income taxpayer subject to NIIT.
A real estate investor sells a rental property for that had an original cost of and accumulated depreciation of . Which portions of the gain are taxed at which rates?
What three requirements must dividends meet to qualify for preferential tax rates, and how does the holding period test differ from the long-term capital gains holding period?
If an FRQ asks you to calculate the maximum federal tax rate on a high-income taxpayer's long-term capital gain from selling corporate stock, what rate should you use and why might it differ from the statutory 20% rate?