Jay Sugarman
About Jay Sugarman
Jay Sugarman, age 62, is Chairman and Chief Executive Officer of Safehold Inc. He has served on the board since 1996 and as CEO since 1997; he was Chairman and CEO of Old SAFE from 2017 until the March 31, 2023 merger of Old SAFE into iStar, which was then renamed Safehold Inc. . He graduated summa cum laude from Princeton (Paul Volcker Award in Economics) and earned an MBA with high distinction from Harvard Business School as a Baker Scholar, receiving the Loeb Award in Finance and the Copeland Award and Gillette Prize in Marketing . Company pay-versus-performance disclosure shows cumulative shareholder return values for an initial $100 investment of $182.42 (2020), $202.71 (2021), $74.15 (2022), $62.44 (2023), and $50.68 (2024), with net income of $59.2m (2020), $73.1m (2021), $135.4m (2022), $(55.0)m (2023), and $105.8m (2024) . In 2024, Safehold achieved an S&P initial rating of BBB+ and a Fitch upgrade to A- under the AIP framework; Core G&A hit the “high” target, although originations were below target given market conditions .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Safehold Inc. (f/k/a iStar) | Director | Since 1996 | Governance continuity; long-term strategic oversight |
| Safehold Inc. (f/k/a iStar) | Chief Executive Officer | Since 1997 | Built public company platform; real estate finance leadership |
| Old SAFE (Safety, Income and Growth, Inc.) | Chairman & Chief Executive Officer | 2017–Mar 31, 2023 | Founded/grew ground lease platform; merged into Safehold |
| Private investment funds | Manager (Burden family, Ziff family) | Not disclosed | Early investment management experience for prominent families |
External Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Not disclosed in 2025 proxy biography for Mr. Sugarman | — | — | — |
Fixed Compensation
Multi-year compensation summary (as reported):
| Metric | 2022 | 2023 | 2024 |
|---|---|---|---|
| Base Salary ($) | $600,000 | $600,000 | $600,000 |
| Bonus ($) | — | — | — |
| Stock Awards ($) | $80,000 | $7,791,612 | — |
| All Other Compensation ($) | $13,050 | $13,812 | $44,601 |
| Total ($) | $693,050 | $8,405,424 | $644,601 |
Perquisites and other: 401(k) match $11,500; life/disability insurance $2,469; dividends on vested units $30,632 (2024 detail) .
Performance Compensation
Annual Incentive Plan (AIP) Framework and Outcomes (2024)
| Metric | Weighting | Threshold | Target | High | Actual Result | Outcome Score |
|---|---|---|---|---|---|---|
| Ground Lease Gross Originations | 30% | $200m | $500m | $650m | $225m | 0.2 |
| Credit Rating | 25% | Downgrade | S&P BBB+ or Fitch A- | S&P BBB+ and Fitch A- | S&P BBB+ and Fitch A- | 3.0 |
| CARET Valuation (min $15m sale) | 20% | No Sale | $2.0B | $2.25B | No Sale | 0.0 |
| Core G&A (excl bonus/SBC/Star fee) | 15% | $39.1m | $36.1m | $34.6m | $34.6m | 3.0 |
| Employee Engagement Score | 10% | 70% | 77% | 80% | 76.5% | 1.9 |
| AIP Pool Funding (adjusted July 2024) | — | $10.2m | $13.2m | $16.2m | $11.5m | Approved at $13.2m |
AIP awards for 2024 (approved/paid Feb 2025): Sugarman received $1,950,000 entirely in equity (fully vested upon grant) . He took no cash AIP for 2024, and voluntarily forewent AIP for 2022–2023 .
| Executive | 2024 AIP Cash ($) | 2024 AIP Equity ($) | Total ($) |
|---|---|---|---|
| Jay Sugarman | — | $1,950,000 | $1,950,000 |
Long-Term Incentive and Vesting
- RSUs: Mr. Sugarman holds time-vesting RSUs granted March 2023 that vest over the first four anniversaries of the merger; 129,798 unvested units at 12/31/2024 valued at $2,398,667 (at $18.48/share) . He acquired 43,266 shares upon vesting in 2024, value realized $921,912 .
- Caret units: 183,750 time-vesting units subject to re-vesting conditions satisfied on March 31, 2025; 12/31/2024 value $35,673,225 based on $194.14 per unit (recent independent transactions) . Company disclosure also notes 735,000 Caret units held directly/indirectly by Mr. Sugarman across plans as of April 1, 2025 .
| Outstanding Equity (12/31/2024) | Quantity | Market/Valuation | Notes |
|---|---|---|---|
| RSUs (time-vesting) | 129,798 | $2,398,667 | Vests over 4 anniversaries from Mar 2023 |
| Caret units (time-vesting) | 183,750 | $35,673,225 | Re-vesting condition satisfied Mar 31, 2025 |
| Stock vested in 2024 | 43,266 shares | $921,912 | Value on vest date |
No stock options or option-like instruments were granted to NEOs in 2024; equity grants were RSUs and Caret units .
Equity Ownership & Alignment
| Ownership Category | Shares/Units | % of Common Outstanding | Notes |
|---|---|---|---|
| Total beneficial ownership (Common) | 2,105,909 shares | 2.9% (71,785,934 shares outstanding) | Includes direct, indirect, RSUs within 60 days |
| Direct Common shares | 1,698,750 shares | — | Within total above |
| RSUs vesting within 60 days | 43,266 shares | — | Settlement net of taxes |
| Indirect (spouse/family trusts/foundation) | 9,590 + 184,360 + 169,943 shares | — | Disclaims beneficial ownership except pecuniary interest |
| Caret units (aggregate holdings reference) | 735,000 units (direct/indirect) | — | Class of membership profit interests in Portfolio Holdings |
Alignment features:
- Ownership guidelines: CEO required to hold equity equal to 10x base salary; all NEOs and directors are currently in compliance .
- Hedging/pledging: Executives and directors are prohibited from hedging; pledging is prohibited except with prior approval per board guidelines .
- Stock ownership equivalents for directors are separate; Mr. Sugarman does not receive director compensation .
Employment Terms
| Term | Provision | Specifics |
|---|---|---|
| Employment agreement | None | Executives are at-will; no guaranteed employment |
| Severance (termination without cause) | Company Severance Plan | Lump sum equal to 6 months’ salary; AIP payment equal to 100% of 2023 AIP; 6 months COBRA employer portion reimbursement; For Mr. Sugarman: cash $300,000; benefits $25,197; equity vesting valued $38,071,892 (as of 12/31/2024) |
| Death/Disability | Equity acceleration | Caret units acceleration valued $35,673,225 (as of 12/31/2024); no cash payment |
| Change-in-control | Single-trigger RSU acceleration | RSUs fully accelerate upon change-in-control even without termination; for Mr. Sugarman RSU value $2,398,667 (as of 12/31/2024) |
| Clawback | Two clawback regimes | Company-specific clawback for fraud/misconduct causing restatement or negative revision within 2 years; NYSE-compliant executive officer clawback for erroneously awarded incentive comp on restatement, recovered reasonably promptly |
| Insider trading | Policy and blackouts | Quarterly blackouts; pre-clearance required; policy attached as Exhibit 19.1 to 2024 10-K |
Board Governance
- Board leadership: Combined Chairman/CEO; lead independent director (Stefan Selig) oversees agendas, executive sessions, CEO review/succession planning, and investor engagement; committees chaired by independent directors .
- Independence: All nominees other than Mr. Sugarman are NYSE-independent (Josephs, Nydick, Ridings, Selig; Hom prior to resignation) .
- Committees (all independent): Audit (Josephs Chair; Ridings; Selig); Compensation (Ridings Chair; Nydick; Selig); Nominating & Corporate Governance (Hom Chair → Nydick to replace; Josephs; Ridings); Investment (Nydick Chair; Hom → Selig; Josephs) .
- Board activity: 8 meetings in 2024; all directors attended ≥75% of board and committee meetings; executive sessions held at least quarterly without management .
- Dual-role implications: The board cites unified leadership benefits with independent oversight via lead director and independent committees; independent directors oversee CEO compensation, finance integrity, succession, governance and risk .
Director Compensation
- Program: Non-employee directors receive $100,000 cash retainer and $135,000 annual RSU grant; lead director additional $75,000; committee chairs: Audit $40,000; Compensation $40,000; Nominating $16,000; Investment $16,000; committee members receive smaller retainers; no meeting fees .
- Mr. Sugarman receives no director compensation as an employee .
Compensation Structure Analysis
- Mix and trends: Mr. Sugarman’s 2024 total was largely fixed cash ($600k salary) plus equity AIP awarded in 2025 and reported in 2025 tables; 2023 included significant stock awards tied to merger-related items and Caret awards (one-time, non-recurring), a factor noted in lower say-on-pay support .
- Shift to RSUs/Caret vs options: Company states no stock options were granted to NEOs in 2024, using RSUs and Caret units subject to multi-year vesting, reducing risk of option repricing .
- Governance safeguards: Ownership guidelines, clawback policies, and prohibition on hedging/pledging strengthen alignment .
Related-Party Transactions
- Policy: All related-party transactions require approval/ratification by disinterested directors; ongoing relationships may be reviewed by Audit Committee; disclosure per SEC rules .
- Specific transactions disclosed involve SpinCo (Star Holdings) management and financing agreements and MSD/GIC shareholder agreements; no transaction identified as involving Mr. Sugarman personally .
Say-on-Pay & Shareholder Feedback
- 2024 say-on-pay support: Approximately 71% of votes cast supported the 2023 compensation, with lower support attributed to one-time merger-related awards, RSU acceleration, and iPIP termination/distributions, which are not part of 2024/go-forward plan .
Equity Ownership & Vesting Schedules (Key Dates)
- RSUs: March 2023 grants vest over four anniversaries from merger date; next vesting dates annually through March 2027 .
- Caret re-vesting: 25% of previously vested Caret units subject to additional vesting conditions satisfied on March 31, 2025 for Mr. Sugarman (continued employment) .
- Change-in-control: RSUs accelerate fully upon change-in-control (single trigger) .
Employment & Contracts Summary
| Item | Status |
|---|---|
| Employment contract | None (at-will) |
| Severance multiple | 6 months base salary; 100% of prior-year AIP; 6 months COBRA employer portion; equity acceleration as specified |
| Non-compete/non-solicit/garden leave | Not disclosed in proxy |
| Post-termination consulting | Not disclosed in proxy |
Investment Implications
- Alignment: Significant personal ownership (2.9% of common) and large unvested RSUs/Caret units, combined with strict ownership guidelines and anti-hedging/pledging, reinforce alignment with long-term TSR and ground lease value creation .
- Retention risk and vesting overhang: Material vesting events (Caret re-vesting on Mar 31, 2025 and continuing RSU schedules) reduce near-term departure risk but can create supply if monetized; RSUs are single-trigger accelerated on change-in-control, aligning incentives in strategic transactions .
- Pay-for-performance: 2024 AIP awards were entirely equity for the CEO and tied to a scorecard weighting credit quality, efficiency, and engagement amid weak originations; the committee funded at target to retain talent in a challenging market, which may temper near-term margin of safety but supports execution continuity .
- Governance: Combined Chair/CEO structure is mitigated by a strong lead independent director and fully independent committees; attendance and executive sessions are robust, limiting independence concerns for most investors .
- Shareholder sentiment: 71% say-on-pay indicates residual concerns from one-time merger-related equity actions; absent repeat of such items, support could normalize, but monitoring future equity grant design and CARET distributions remains prudent .