Orange County Bancorp, Inc. · NASDAQ:OBT

Orange County Bancorp — Debt Investor Presentation (September 2025)

40 slides from Orange County Bancorp's debt investor presentation, Sep 25, 2025

  1. Slide 1: Subordinated Notes Offering

    INVESTOR Presentation September 2025 Subordinated Notes Offering

  2. Slide 2: Disclaimer - Forward-Looking Statements

    Disclaimer Forward - Looking Statements This presentation and any other written or oral statements made by us from time to time may contain forward - looking statements w ithin the meaning of the Private Securities Litigation Reform Act of 1995, which may be identified by the use of such words as “m

  3. Slide 3: Safe Harbor Statement

    Safe Harbor Statement Safe Harbor Statement The information contained in this presentation is a summary and it is not complete. It has been prepared for use only in conn ect ion with the private placement (the “Placement”) of securities (the “Securities”) of Orange County Bancorp, Inc. (the “Company

  4. Slide 4: Preliminary Term Sheet

    Preliminary Term Sheet 4 Issuer Orange County Bancorp, Inc. Security Fixed - to - Floating Rate Subordinated Notes due 2035 Use of Proceeds Refinance outstanding subordinated debt and for general corporate purposes Term 10 Years Principal Amount $25.0 million Call 5 Years @ Par Placement Agent Offer

  5. Slide 5: Today's Presenters / Management Team

    • Mr. Sousa became Chief Lending Officer of the Bank in July 2024 after serving as Executive Vice President and Chief Commercial Banking Officer since 2020. • Prior to joining the Bank, Mr. Sousa served as SVP and Branch Administrator at Hudson Valley Bank. Greg Sousa EVP and Chief Lending Officer M

  6. Slide 6: Investment Highlights

    Investment Highlights 6 1) For the quarter ended June 30, 2025. Source: S&P Capital IQ Pro. Strong and Experienced Management Team Successful and Ongoing Expansion of Market Footprint Highly Attractive Market Geography and Scarcity Value of Franchise Ability to Take Advantage of M&A Driven Market Di

  7. Slide 7: Franchise Overview

    Franchise Overview 7 1) There are 2 branches located in Middletown and 2 branches located in the Bronx. Source: S&P Capital IQ Pro. Background ▪ Successfully completed IPO and NASDAQ listing in August 2021 ▪ Bank was established in 1892 and has operated successfully for over 133 years ▪ Headquartere

  8. Slide 8: Franchise Located in Highly Attractive Markets

    1HZ<RUN3ULYDWH% 7& 2UDQJH&RXQW\%DQFRUS 1RUWKHDVW&RPPXQLW\ :DOGHQ6% &RQQHFW2QH 7RPSNLQV)LQDQFLDO 7UXVW&R%DQN&RUS :DOONLOO9DOOH\0+& 5LGJHZRRG6% 7%%,QYHVWPHQWV//& 5KLQHEHFN0+& )LUVW*UHHQZLFK)LQDQFLDO )LUVW)HGHUDO6DYLQJV 9HFWD,QF ,%&%DQFRUS,QF Franchise Located in Highly Attractive Markets 8 Attractive

  9. Slide 9: Structure & Scope

    Structure & Scope Balanced, Client - Driven Business Model 9 Business Banking Private Banking Orange Wealth Management • 17 branches and LPOs • Focus on small to medium size businesses, professionals, and non - profit entities in the communities served • Seasoned lenders with significant regional an

  10. Slide 10: Competitive Strengths

    Competitive Strengths 10 1) Local peers include NASDAQ, NYSE and NYSEAM traded U.S. banks and thrifts in the NYC MSA with total assets less than $50 bill ion as of 2Q 2025. Excludes merger targets and mutuals. Values reflect median of peer data for respective metrics. Note: Financial data as of June

  11. Slide 11: Business Strategy

    Business Strategy 11 Note: Financial data as of June 30, 2025 unless otherwise noted. Course: Company filings, S&P Capital IQ Pro. Leverage Relationships to Drive Organic Growth Derive Loan Growth Through Relationship - Based Model Continue to Grow Core Deposit Franchise Continue to Build Fee - Base

  12. Slide 12: Transformation, Significant Growth and Expansion

    <7' <7' Transformation, Significant Growth and Expansion 12 Significant Investments in People, Systems and Footprint Expansion… … Has Led to Enhanced Profitability and Peer Outperformance FTE Count Best in Class Profitability Return on Average Assets (%) Noninterest Expense ($M) 1) Non - GAAP financ

  13. Slide 13: Consistent History of Growth

    <7' <7' <7' <7' Consistent History of Growth 13 Note: Financial data as of the six months ended June 30, 2025 unless otherwise noted. Data as of December 31 for respective y ear s. Source: Company filings, S&P Capital IQ Pro. Current Success is Attributed to Disciplined Organic Growth Gross Loans ($

  14. Slide 14: Strong and Consistent Historical Profitability

    <7' <7' 2%7 /RFDO3HHUV ñ Strong and Consistent Historical Profitability 14 Net Interest Margin (%) Net Income ($M) Pre - Provision Net Revenue ($M) ROAA and ROAE (%) Success Maintaining Strong Profitabilit y Metrics 1) Local peers include NASDAQ, NYSE and NYSEAM traded U.S. banks and thrifts in the

  15. Slide 15: Stable Regulatory Capital Position

    <7' <7' <7' <7' Stable Regulatory Capital Position 15 1) Non - GAAP financial metric. See slides 39 and 40 for applicable reconciliation 2) Bank level Call Report data. Note: Financial data for the six months ended June 30, 2025 unless otherwise noted. Data as of December 31 for respective yea rs. S

  16. Slide 16: Diversified Revenue Sources

    <7' <7' 6HUYLFH&KDUJHV RQ'HSRVLWV 7UXVW,QFRPH ,QYHVWPHQW$GYLVRU\ +9,$ (DUQLQJV RQ%2/, 3URFHHGV IURP%2/, *DLQRQ6DOH RI$VVHWV ò 2WKHU ,QYHVWPHQW &RPSDQ\ ,QGLYLGXDOV 3URILWVKDULQJ &RUSRUDWLRQV +LJK1HW:RUWK &KDULW\ 2WKHU ó Diversified Revenue Sources 1) Based on annualized 2Q 2025 trust and investment a

  17. Slide 17: Loan Composition

    :HVWFKHVWHU 2UDQJH %URQ[ 2WKHU1< &RXQWLHV 2WKHU 5RFNODQG 1HZ-HUVH\ 0DQKDWWDQ &5( & , &5( &RQVWUXFWLRQ 5HVLGHQWLDO5( +RPH(TXLW\ &RQVXPHU Loan Composition 17 1) CRE and CRE Construction loans as a % of Total Risk - Based Capital. Reflects bank level Call Report data. 2) Reflects weighted average yield

  18. Slide 18: Overview of Commercial Real Estate Portfolio

    0XOWLIDPLO\ 2WKHU 122 5HWDLO 2IILFH 0L[HG8VH ,QGXVWULDO :DUHKRXVH &RQVWUXFWLRQ /DQG'HYHORS 2WKHU 22 Overview of Commercial Real Estate Portfolio 18 Note: Financial data as of June 30, 2025. Source: Company documents. CRE Portfolio Geographic Composition CRE Portfolio by Property Type :HVWFKHVWHU 2UD

  19. Slide 19: Overview of Multifamily Portfolio

    Overview of Multifamily Portfolio 19 Note: Financial data as of June 30, 2025. Source: Company documents. Multifamily Portfolio Detail Multifamily Portfolio Geographic Composition Weighted Average LTV 53.9% Average Loan Size $2.45 Million % of Total Multifamily Portfolio Portfolio Characteristic 23.

  20. Slide 20: Overview of CRE Office Portfolio

    Overview of CRE Office Portfolio 20 Note: Financial data as of June 30, 2025. Source: Company documents. Office Portfolio Overview % of Total Office Portfolio Portfolio Characteristic 1.7% % of Portfolio in the Bronx and Queens None % of Portfolio in Manhattan 8.6% % Maturing in 2025 7.4% % Maturing

  21. Slide 21: Overview of C&I Portfolio

    Orange 18% Westchester 22% Other 26% Bergen 1% Rockland 5% Nassau 3% Other NY Counties 25% Other NJ Counties 1% Overview of C&I Portfolio 21 Note: Financial data as of June 30, 2025. Source: Company documents. C&I Portfolio Geographic Composition C&I Portfolio by Industry Total C&I: $247 Million Tot

  22. Slide 22: Top Largest Recourse Borrower Relationships

    Top 20 Largest Recourse Borrower Relationships 22 Note: Financial data as of June 30, 2025. Source: Company documents. ($000s) Loan Type(s) Number of Total Loans Tenure of Relationship Total Exposure Total Balance As a (%) of Total Loans Customer 1 CRE Non-OO 16 6 Years $43,545 $43,545 2.27% Custome

  23. Slide 23: Credit Quality

    Credit Quality 23 1) Local peers include NASDAQ, NYSE and NYSEAM traded U.S. banks and thrifts in the NYC MSA with total assets less than $50 bill ion as of 2Q 2025. Excludes merger targets and mutuals. Values reflect median of peer data for respective metrics. Note: Financial data as of or for the

  24. Slide 24: Leading Core Deposit Franchise

    $YJ )HG)XQGV5DWH 2%7 /RFDO3HHUV ó Orange 38% Westchester 39% Rockland 9% Bronx 5% Other 9% Leading Core Deposit Franchise Areas of Focus Keys to Success x Dedicated deposit relationship managers x Investment into customer experience/cash management product suite x Obtain deposit relationships at loa

  25. Slide 25: Top Largest Depositor Relationships

    Top 20 Largest Depositor Relationships 25 Note: Financial data as of June 30, 2025. Source: Company documents. ($000s) Depositor Type Tenure of Relationship Total Deposit Balance As a (%) of Total Deposits Customer 1 Municipality 52 Years $63,027,075 2.77% Customer 2 Medical 6 Years $52,481,738 2.31

  26. Slide 26: Liquidity Overview

    Liquidity Overview 26 Note: Financial data as of June 30, 2025 unless otherwise noted. Source: Company filings. Strong Recent Deposit Growth and Significant Borrowing Capacity • Borrowings consist of both short - term and long - term borrowings and provide the Company with one of its sources of fund

  27. Slide 27: Conservatively Managed Securities Portfolio

    8 6 *RYHUQPHQW $JHQFLHV 0RUWJDJH EDFNHG 6HFXULWLHV &RUSRUDWH 6HFXULWLHV 0XQLFLSDO 6HFXULWLHV Conservatively Managed Securities Portfolio 27 Note: Financial data as of June 30, 2025. Source: Company documents, Company filings. ▪ $ 410.8 million in securities, primarily concentrated in mortgage - back

  28. Slide 28: Interest Rate Sensitivity

    At June 30, 2025 Change in Interest Rates Net Interest Income Year 1 Change (basis points)² Year 1 Forecast Base Case (Dollars in thousands) Shock Up 200 bps 111,172 3,682 Shock Up 100 bps 109,526 2,036 Base 107,490 - Shock Down 100 bps 105,264 (2,226) Shock Down 200 bps 102,985 (4,505) Interest Rat

  29. Slide 29: Tangible Common Equity & Capital Management

    4 4 4 4 Tangible Common Equity & Capital Management 29 Tangible Common Equity Ratio¹ Capital Overview 1) Non - GAAP financial metric, see slides 39 and 40 for applicable reconciliation. 2) Local peers include NASDAQ, NYSE and NYSEAM traded U.S. banks and thrifts in the NYC MSA with total assets less

  30. Slide 30: Pro Forma Capital Position & Loan Concentration

    OBT Pro Forma 3 OBT As Reported Pro Forma Capital Position & Loan Concentration 30 Capital Ratios 9.46% 9.48% TCE / TA 1 11.82% 11.84% TCE / TA (Ex. AOCI) 1 12.43% 12.40% Tier 1 Leverage Ratio 2 16.39% 16.36% Tier 1 Capital Ratio 2 17.65% 17.61% Total Capital Ratio 2 377% 377% CRE Concentration 2 (%

  31. Slide 31: Pro Forma Interest Coverage and Double Leverage

    Pro Forma Interest Coverage and Double Leverage 31 1) Assumes all net proceeds after repayment of existing subordinated debt, except for two years of interest coverage, are downst rea med to the Bank as equity. 2) Includes amortization of $250,000 of one - time offering expenses, amortized over five

  32. Slide 32: 2025 Trends and Company Highlights

    2025 Trends and Company Highlights 32 Continued High Performance During Turbulent Industry Period x Consistent growth and compelling financial performance, maintaining a net interest margin above peers and outperforming on ROAA and ROAE 1 x Highly successful deposit gathering strategy maintains a lo

  33. Slide 33: 33

    33

  34. Slide 34: Business Evolution and Milestones

    Business Evolution and Milestones 34 1905: Bank abbreviated name to Orange County Trust Company 2007: Orange County Bancorp organized to serve as the bank holding company for the Bank 2018: Raised $16M in private placement of common stock 2014: Mike Gilfeather hired as President & CEO; Board sets ne

  35. Slide 35: Selected Comparable Group

    Selected Comparable Group Note: Peers include NASDAQ, NYSE and NYSEAM traded U.S. banks and thrifts in the NYC MSA with total assets under $50 billion as of 2Q 2025, excluding merger targets and mutuals. Institutions not shown pro forma for pending or recently completed acquisitions. Source: S&P Cap

  36. Slide 36: Consolidated Historical Balance Sheet

    Consolidated Historical Balance Sheet 36 As of the Year Ended December 31, As of the 6-Months 2021 2022 2023 2024 Ended June 30, 2025 Assets Cash and due from banks $306,179 $86,081 $147,383 $150,334 $175,606 Investment securities — available-for-sale 464,797 533,461 489,948 443,775 410,814 Restrict

  37. Slide 37: Consolidated Historical Income Statement

    Consolidated Historical Income Statement 37 1) Non - GAAP financial metric. See slide 39 and 40 for applicable reconciliation. Note: Dollars in thousands, except per share amounts. Source: Company filings. For the Year Ended December 31, For the 6-Months 2021 2022 2023 2024 Ended June 30, 2025 Inter

  38. Slide 38: Board of Directors

    1) Director ages per Company Proxy Statement filed April 11, 2025. 2) To the Company’s knowledge, there is no written agreement amongst members of the Morrison family to act in concert. As of Jun e 3 0, 2025, William D. Morrison and his relatives collectively beneficially owned approximately 20.74%

  39. Slide 39: Tangible Common Equity Ratios

    Tangible Common Equity Ratios As of the Year Ended December 31, As of the 6-Months 2021 2022 2023 2024 Ended June 30, 2025 Total Common Equity $182,836 $138,138 $165,376 $185,531 $252,589 Goodwill 5,359 5,359 5,359 5,359 5,359 Other Intangibles 1,678 1,392 1,107 821 678 Less: Total Intangible Assets

  40. Slide 40: Tangible Common Equity Ratios (Quarterly)

    Tangible Common Equity Ratios (Quarterly) As of the Quarter Ended June 30, 2024 September 30, 2024 December 31, 2024 March 31, 2025 June 30, 2025 Total Common Equity $177,544 $193,094 $185,531 $201,324 $252,589 Goodwill 5,359 5,359 5,359 5,359 5,359 Other Intangibles 964 892 821 750 678 Less: Total

Orange County Bancorp — Debt Investor Presentation (September 2025) on 6ix