| Step | Cash donation · sell first, then donate | Direct security donation Recommended |
|---|---|---|
| Capital gain inclusion | 50% (normal rule) | 0% (donation of qualifying listed securities) |
| Taxable portion of gain | Half of the gain is corporate taxable income | None of the gain is taxable |
| Amount credited to CDA | Only the untaxed 50% of the gain | The entire 100% of the gain |
| Donation deduction | Equal to cash proceeds donated | Equal to full FMV of securities donated |
| Charity receives | Same net proceeds (after any tax drag on the sale) | Full FMV of the securities |
| Item | Sell shares, donate cash | Donate shares directly Recommended |
|---|---|---|
| Fair market value donated | $1,000,000 | $1,000,000 |
| Accrued capital gain | $800,000 | $800,000 |
| Taxable capital gain | $400,000 (50% inclusion) | $0 (0% inclusion) |
| Amount credited to CDA | $400,000 | $800,000 |
| Donation deduction | $1,000,000 (from cash donated) | $1,000,000 (from FMV of shares) |
| Tax-free capital dividend available | $400,000 | $800,000 |
| Extra dividend from donating shares directly | — | +$400,000 |
| Outcome | Do nothing | Sell + donate cash | Donate securities + insurance Recommended |
|---|---|---|---|
| Tax on the $800,000 gain | None (until eventual disposition) | Tax on $400,000 taxable half | None: 0% inclusion |
| Donation deduction | None | Equal to cash donated | Equal to full FMV of securities |
| CDA credit generated | None | $400,000 | $800,000 |
| Estate value after the gift | Full $1,000,000 retained (no gift made) | Reduced by $1,000,000, partially offset by CDA | Reduced by $1,000,000, offset by CDA now and insurance death benefit later |
| Family’s after-tax result | No charitable impact | Partial tax-free recovery | Largest tax-free recovery, plus estate value replaced at death |