[sheet: Cover & Taxpayer Info]

[sheet: Cover & Taxpayer Info]
Field | Value
Tax Year | 2023
Taxpayer Name | Jonathan Robert Caldwell
SSN (last four) | XXX-XX-4781
Date of Birth | March 14, 1956
Taxpayer Address | 418 East 72nd Street, Apt. 14A, New York, NY 10021
Domicile (State) | New York
Citizenship | United States
Spouse Name | Eleanor Victoria Caldwell
Spouse SSN (last four) | XXX-XX-6203
Filing Status | Married — gift splitting elected for foundation contribution only
Consent to Gift Splitting (Spouse) | Yes — Eleanor V. Caldwell consents to split $10,000,000 foundation gift ($5,000,000 attributable to each spouse)
Has donor previously filed Form 709? | Yes
Prior Taxable Gifts (cumulative) | $6,750,000
2023 Lifetime Gift Tax Exemption | $12,920,000
Remaining Exemption Before This Return | $6,170,000 ($12,920,000 – $6,750,000)
Preparer — Law Firm | Calderwood & Harkness LLP
Preparer — Tax Specialist | Sylvia Hartwell, Specialist Partner (Tax)
Preparer Address | 375 Park Avenue, 42nd Floor, New York, NY 10152
Coordinating Accountant | Strathmore Corporation & Greaves LLP — Martin J. Prescott, CPA
Accountant Address | 600 Third Avenue, 28th Floor, New York, NY 10016
C&H Matter No. | 1034-00004
C&H Billing Code | 78412-JRC
Draft Date | August 1, 2023
Status | DRAFT — For review by Strathmore Corporation & Greaves LLP prior to filing
[sheet: Schedule A — Taxable Gifts]
Item No. | Date of Gift | Description of Gift | Donee / Trust Name | Donee EIN or Relationship | FMV at Date of Gift | Valuation discounts Applied | Gift Value After discounts | Retained Interest / Annuity Value | Taxable Gift Value | Annual Exclusion Applied | Net Taxable Gift | Gift Splitting — Donor's Share | Gift Splitting — Spouse's Share | Notes / IRC Section
1 | 2023-04-15 | Caldwell 2023 Securities GRAT (GRAT A) — Transfer of $60,000,000 in publicly traded securities to zeroed-out GRAT; 2-year term; annuity of $32,195,122/yr | Caldwell 2023 Securities GRAT | Irrevocable Trust — Grantor: J.R. Caldwell | $60,000,000 | None (publicly traded securities — no discount) | $60,000,000 | $60,000,000 | $0 | $0 | $0 | $0 | $0 | IRC § 2702 zeroed-out GRAT; § 7520 rate 5.0% (March 2023); remainder to Caldwell Family Dynasty Trust; taxable gift = $0
2 | 2023-05-01 | Caldwell 2023 Realty GRAT (GRAT B) — Transfer of 59.7% membership interest in Stonecrest Realty Holdings LLC (NY LLC) to zeroed-out GRAT; 3-year term; annuity of $29,375,859/yr | Caldwell 2023 Realty GRAT | Irrevocable Trust — Grantor: J.R. Caldwell | $80,000,000 | 25% combined lack-of-marketability and lack-of-control discount; post-discount FMV = $60,000,000 | $60,000,000 | $60,000,000 | $0 | $0 | $0 | $0 | $0 | IRC § 2702 zeroed-out GRAT; § 7520 rate 5.0% (April 2023); pre-discount FMV $80,000,000; post-discount FMV $60,000,000; remainder to Caldwell Family Dynasty Trust; taxable gift = $0. Appraisal by Ashford Valuation Group LLC (Dr. Leonard K. Whitfield, ASA)
3 | 2023-06-01 | Caldwell 2023 Carried Interest GRAT (GRAT C) — Transfer of LP interests in Caldwell Ridgeline Fund IV LP ($12M), Fund V LP ($14M), and carried interest in Fund VI LP ($12M) to zeroed-out GRAT; 3-year term; annuity of $13,953,759/yr | Caldwell 2023 Carried Interest GRAT | Irrevocable Trust — Grantor: J.R. Caldwell | $38,000,000 | 35% discount on Fund IV & V LP interests ($26M × 0.65 = $16,900,000); 30% discount on Fund VI carried interest ($12M × 0.70 = $8,400,000); blended post-discount FMV = $25,300,000 | $25,300,000 | $25,300,000 | $0 | $0 | $0 | $0 | $0 | IRC § 2702 zeroed-out GRAT; § 7520 rate 5.0% (May 2023); pre-discount FMV $38,000,000; post-discount FMV $25,300,000; remainder to Caldwell Family Dynasty Trust; taxable gift = $0. Appraisal by Ashford Valuation Group LLC
4 | 2023-04-01 | Cash gift to Caldwell Family Dynasty Trust (Delaware irrevocable trust; co-trustees: Thomas R. Caldwell and Northgate Trust Company of Delaware) | Caldwell Family Dynasty Trust | Irrevocable Trust — Delaware situs | $5,000,000 | None (cash) | $5,000,000 | $0 | $5,000,000 | $0 | $5,000,000 | $5,000,000 | $0 | Completed gift of cash; uses $5,000,000 of remaining lifetime gift tax exemption ($6,170,000 available); no gift tax due; GST exemption of $5,000,000 allocated (see Schedule C)
5 | 2023-04-01 | Cash contribution to The Caldwell Family Foundation (NY not-for-profit corporation, EIN 88-3021547) — Joint gift with Eleanor V. Caldwell; total $10,000,000; gift-split 50/50 | The Caldwell Family Foundation | EIN: 88-3021547 — IRC § 501(c)(3) private foundation | $10,000,000 | None (cash) | $10,000,000 | $0 | $10,000,000 | $0 | $5,000,000 | $5,000,000 | $5,000,000 | Gift splitting elected; $5,000,000 attributable to each spouse. Charitable deduction offsets taxable gift. Charitable deduction limited to 30% of AGI for private foundation cash contributions (2022 AGI $22,500,000 × 30% = $6,750,000 Yr 1 deduction; $3,250,000 carried forward up to 5 years). Taxable gift = $0 after charitable deduction.
6 | 2023-03-15 | ILIT annual premium contribution — Cash to Caldwell Family Insurance Trust for Beacon Life Assurance Company second-to-die universal life policy (Policy No. BLA-2023-77419; $15,000,000 death benefit); Crummey withdrawal rights for 3 beneficiaries | Caldwell Family Insurance Trust (ILIT) | Irrevocable Trust — Trustee: Northgate Trust Company of Delaware | $187,500 | None (cash) | $187,500 | $0 | $187,500 | $51,000 | $136,500 | $136,500 | $0 | Annual exclusion: 3 Crummey beneficiaries × $17,000 = $51,000. Remaining $136,500 uses lifetime exemption. Crummey beneficiaries: Thomas R. Caldwell, Katherine C. Hartfield, Olivia G. Caldwell ($5,000 withdrawal right each, annual exclusion of $17,000 each).
[sheet: Schedule A Summary]
Line Item | Amount | Notes
Total FMV of All Gifts (pre-discount) | $178,187,500 | Sum of all transfers at pre-discount FMV: $60M + $80M + $38M + $5M + $10M + $187,500
Total Valuation discounts Applied | $32,700,000 | GRAT B: $20,000,000 discount; GRAT C: $12,700,000 discount; total $32,700,000
Total Gifts After discounts | $145,487,500 | $178,187,500 – $32,700,000
Total Retained Interests (GRAT Annuities) | $145,300,000 | GRAT A: $60,000,000 + GRAT B: $60,000,000 + GRAT C: $25,300,000 = $145,300,000
Total Taxable Gift Value (before exclusions/deductions) | $10,187,500 | $5,000,000 (Dynasty Trust) + $5,000,000 (Foundation — donor's share) + $187,500 (ILIT)
Less: Annual Exclusions | $51,000 | ILIT Crummey: 3 × $17,000 = $51,000
Less: Charitable Deduction (Foundation — donor's share) | $5,000,000 | $5,000,000 attributable to Jonathan R. Caldwell; charitable deduction offsets gift
Total Taxable Gifts — Current Year | $5,136,500 | $5,000,000 (Dynasty Trust) + $136,500 (ILIT premium net of exclusion)
Prior Taxable Gifts (cumulative, all prior years) | $6,750,000 | Per Caldwell's records
Total Cumulative Taxable Gifts | $11,886,500 | $6,750,000 + $5,136,500
2023 Applicable Exclusion Amount (Unified Credit) | $12,920,000 | Per IRS — 2023 lifetime gift/estate tax exemption
Tentative Tax on Cumulative Gifts | $0 | Cumulative gifts ($11,886,500) do not exceed exemption ($12,920,000)
Less: Unified Credit | $0 | Credit equals tentative tax — no tax due
Gift Tax Due | $0 | No gift tax owed for 2023
Remaining Lifetime Exemption After This Return | $1,033,500 | $12,920,000 – $11,886,500 = $1,033,500. Note: $1,170,000 – $136,500 (ILIT) = $1,033,500
[sheet: Schedule B — Prior Gifts]
Year | Description of Prior Gifts | Taxable Amount | Cumulative Total
Prior years (aggregate) | Taxable gifts reported on prior Forms 709 — details per Strathmore Corporation & Greaves LLP records | $6,750,000 | $6,750,000
2023 (current year) | Dynasty Trust ($5,000,000) + ILIT premium net ($136,500) | $5,136,500 | $11,886,500
[sheet: Schedule C — GST Exemption]
Item No. | Trust / Transfer | Date of Transfer | FMV of Transfer | GST Exemption Allocated | Inclusion Ratio | ETIP Applicable? | Notes
1 | Caldwell Family Dynasty Trust — Initial cash funding | 2023-04-01 | $5,000,000 | $5,000,000 | 0.00 | No | Outright gift of cash to dynasty trust; GST exemption allocated to achieve 0.00 inclusion ratio; trust beneficiaries include skip persons (grandchildren and future issue per stirpes)
2 | Caldwell 2023 Securities GRAT (GRAT A) — Remainder interest | 2023-04-15 | $0 | $0 | N/A — ETIP | Yes — ETIP applies during GRAT term | GRAT remainder interest not eligible for GST exemption allocation during the estate tax inclusion period (ETIP) under IRC § 2642(f). GST exemption will be allocated upon termination of GRAT A (April 15, 2025). Zeroed-out gift value = $0.
3 | Caldwell 2023 Realty GRAT (GRAT B) — Remainder interest | 2023-05-01 | $0 | $0 | N/A — ETIP | Yes — ETIP applies during GRAT term | GRAT remainder interest not eligible for GST exemption allocation during ETIP. GST exemption will be allocated upon termination of GRAT B (May 1, 2026). Zeroed-out gift value = $0.
4 | Caldwell 2023 Carried Interest GRAT (GRAT C) — Remainder interest | 2023-06-01 | $0 | $0 | N/A — ETIP | Yes — ETIP applies during GRAT term | GRAT remainder interest not eligible for GST exemption allocation during ETIP. GST exemption will be allocated upon termination of GRAT C (June 1, 2026). Zeroed-out gift value = $0.
5 | Caldwell Family Insurance Trust (ILIT) — Annual premium contribution | 2023-03-15 | $187,500 | $0 | N/A | No | ILIT beneficiaries are children (non-skip persons for GST purposes). No GST exemption allocated to ILIT premium gifts.
[sheet: GRAT Annuity Computations]
GRAT | Funding Date | Corpus — Pre-discount FMV | Valuation discount | Corpus — Post-discount FMV | § 7520 Rate | § 7520 Rate Month | GRAT Term (years) | Annuity Payment | Present Value of Annuity Stream | Taxable Gift (Remainder Interest) | Grantor Age at Funding | Mortality Factor Applied | Trustee During Term | Remainder Beneficiary
GRAT A — Caldwell 2023 Securities GRAT | 2023-04-15 | $60,000,000 | 0% | $60,000,000 | 5.0% | March 2023 | 2 | $32,195,122 | $60,000,000 | $0 | 67 | Per IRS Table B / Table S (age 67) | Jonathan R. Caldwell | Caldwell Family Dynasty Trust
GRAT B — Caldwell 2023 Realty GRAT | 2023-05-01 | $80,000,000 | 25% | $60,000,000 | 5.0% | April 2023 | 3 | $29,375,859 | $80,000,000 | $0 | 67 | Per IRS Table B / Table S (age 67) | Jonathan R. Caldwell | Caldwell Family Dynasty Trust
GRAT C — Caldwell 2023 Carried Interest GRAT | 2023-06-01 | $38,000,000 | Blended: 35% LP / 30% carried | $25,300,000 | 5.0% | May 2023 | 3 | $13,953,759 | $38,000,000 | $0 | 67 | Per IRS Table B / Table S (age 67) | Jonathan R. Caldwell | Caldwell Family Dynasty Trust