HTH Hilltop Holdings Inc.

Did the company actually spend money buying back stock in 3+ of the last 4 quarters?

Bought back stock in 3/4 quarters. Q1 2026: $33M, Q3 2025: $0M, Q2 2025: $10M, Q1 2025: $10M

Is the most recent quarter's buyback spend more than 15% above the trailing average?

Latest quarter $33M vs trailing avg $7M (+403%)

What percentage of free cash flow is going to buybacks? Bull: 30%+. Bear: negative FCF or no buybacks.

Negative FCF ($-482M), buybacks not supported by cash flow

How fast are they shrinking the float? Bull: 2%+ annually. Bear: under 0.5%.

Repurchased 1,744,529 shares = 2.9% of 59,540,484 outstanding (annualized)

Are officers and directors buying stock with their own money on the open market?

10 open-market purchases by 1 insiders

• SOBEL JONATHAN S (Hilltop Securities Chairman) bought 10,000 shares at $35.36 on 2025-08-27
• SOBEL JONATHAN S (Hilltop Securities Chairman) bought 10,000 shares at $35.21 on 2025-08-26
• SOBEL JONATHAN S (Hilltop Securities Chairman) bought 10,000 shares at $34.75 on 2025-08-25
• SOBEL JONATHAN S (Hilltop Securities Chairman) bought 10,000 shares at $34.57 on 2025-08-22
• SOBEL JONATHAN S (Hilltop Securities Chairman) bought 10,000 shares at $33.19 on 2025-08-21
• SOBEL JONATHAN S (Hilltop Securities Chairman) bought 10,000 shares at $32.93 on 2025-08-20
• SOBEL JONATHAN S (Hilltop Securities Chairman) bought 10,000 shares at $32.92 on 2025-08-19
• SOBEL JONATHAN S (Hilltop Securities Chairman) bought 10,000 shares at $31.97 on 2025-08-18
• SOBEL JONATHAN S (Hilltop Securities Chairman) bought 10,000 shares at $32.37 on 2025-08-15
• SOBEL JONATHAN S (Hilltop Securities Chairman) bought 10,000 shares at $32.70 on 2025-08-14

Are both company buybacks and insider buying independently active? Bull when the company is buying back stock in 2+ quarters and insiders have made 2+ open-market purchases.

Company buybacks in 3 quarters and 10 insider purchases by 1 insiders (no calendar overlap, but both independently active)

Over the last 90 days, are insiders net buyers or net sellers on the open market?

Insiders bought $0M, sold $10M in the last 90 days (net selling)

Active buyback + insiders net selling 3x+ more than buying. Company cash may be supporting price while insiders exit.

Company buying back stock while insiders sold 3.6x more than bought. 3 C-suite officers among sellers

• Bornemann Keith E. (Chief Accounting Officer) sold 2,000 shares on 2026-05-05
• Thompson Steve B (PrimeLending President and CEO) sold 9,025 shares on 2026-02-06
• Winges Martin Bradley (Hilltop Securities CEO) sold 10 shares on 2026-02-03
• Winges Martin Bradley (Hilltop Securities CEO) sold 2,408 shares on 2026-02-03
• Winges Martin Bradley (Hilltop Securities CEO) sold 23,582 shares on 2026-02-03
• Bornemann Keith E. (Chief Accounting Officer) sold 2,200 shares on 2025-11-25
• Thompson Steve B (PrimeLending President and CEO) sold 11,687 shares on 2025-08-13
• Thompson Steve B (PrimeLending President and CEO) sold 6,640 shares on 2025-08-15
• Thompson Steve B (PrimeLending President and CEO) sold 5,332 shares on 2024-08-29