Q4 1 Forward-Looking Statements This presentation may include - PowerPoint PPT Presentation

2018 Investor Presentation Q4 1

Forward-Looking Statements This presentation may include forward-looking statements, both with respect 15) the effect on our investment portfolios of changing financial market to Argo Group and its industry, that reflect our current views with respect to conditions including inflation, interest rates, liquidity and other factors; future events and financial performance. These statements are made 16) acts of terrorism or outbreak of war; and 17) availability of reinsurance pursuant to the safe harbor provisions of the Private Securities Litigation and retrocessional coverage, as well as management’s response to any Reform act of 1995. Forward-looking statements include all statements that of the aforementioned factors. do not relate solely to historical or current facts, and can be identified by the use of words such as “expect,” “intend,” “plan,” “believe,” “do not believe,” In addition, any estimates relating to loss events involve the exercise of “aim,” “project,” “anticipate,” “seek,” “will,” “likely,” “assume,” “estimate,” “may,” considerable judgments and reflect a combination of ground-up evaluations, “continue,” “guidance,” “objective,” “outlook,” “trends,” “future,” “could,” information available to date from brokers and pedants, market intelligence, “would,” “should,” “target,” “on track,” and similar expressions of a future or initial tentative loss reports, and other sources. The actuarial range of forward-looking nature. All forward-looking statements address matters that reserves and management’s best estimate is based on our then-current state involve risks of knowledge including explicit and implicit assumptions relating to the pattern and uncertainties, many of which are beyond Argo Group’s control. of claim development, the expected ultimate settlement amount, inflation and Accordingly, there are or will be important factors that could cause actual dependencies between lines of business. Our internal capital model is used to results to differ materially from those indicated in such statements and, consider the distribution for reserving risk around this best estimate and therefore, you should not place undue reliance on any such statements. predict the potential range of outcomes. However, due to the complexity of We believe that these factors include, but are not limited to, the following: factors contributing to the losses and preliminary nature of the information 1) unpredictability and severity of catastrophic events; 2) rating agency used to prepare these estimates, there can be no assurance that Argo actions; 3) adequacy of our risk management and loss limitation methods; Group’s ultimate losses will remain within the stated amount. 4) cyclicality of demand and pricing in the insurance and reinsurance markets;5) statutory or regulatory developments including tax policy, The foregoing review of important factors should not be construed as reinsurance and other regulatory matters; 6) our ability to implement our exhaustive and should be read in conjunction with the other cautionary business strategy; statements that are included herein and elsewhere, including the risk factors 7) adequacy of our loss reserves; 8) continued availability of capital and included in our most recent reports on Form 10-K and Form 10-Q and other finance; 9) retention of key personnel; 10) competition; 11) potential loss documents of Argo Group on file with or furnished to the U.S. Securities and of business from one or more major insurance or reinsurance brokers; Exchange Commissions (“SEC”). Any forward-looking statements made in this 12) our ability to implement, successfully and on a timely basis, complex presentation are qualified by these cautionary statements, and there can be infrastructure, distribution capabilities, systems, procedures, and internal no assurance that the actual results or developments anticipated by Argo controls, and to develop accurate actuarial data to support the business Group will be realized, or even if substantially realized, that they will have the and regulatory and reporting requirements; 13) general economic and market expected consequences to. or effects on, Argo Group or its business or conditions (including inflation, volatility in the credit and capital markets, operations. Except as required by law, Argo Group undertakes no obligation to interest rates, and foreign currency exchange rates); 14) the integration update publicly or revise forward-looking statements, whether as a result of businesses we may acquire or new business ventures we may start; of new information, future developments or otherwise. 2

Leading Specialty Platform TTM * NWP ** by Business Mix Argo Franchise Overview • Global underwriter of specialty insurance and reinsurance Property • Strategically located in major insurance centers Specialty Liability • Across the U.S. Professional Lines • Bermuda • London • Zurich • Dubai TTM NWP by Business Type • Singapore • Established presence in desirable markets Primary Insurance • Consistent Leader in U.S. excess and surplus lines for more than two decades Reinsurance • Strong U.S. retail specialty franchise • Top Lloyd’s Syndicate in 2018 by stamp capacity • Leading Bermuda insurance and reinsurance platforms • Diversified by geography, product and strategy • Broad and strong producer relationships TTM NWP by Geography • Agents, brokers, wholesalers and coverholders • “A” (Excellent) A.M. Best rating, stable outlook United States London • “A-” (Strong) S&P rating, positive outlook Bermuda Brazil, Asia and Europe *TTM = trailing twelve months 3 **NWP = net written premiums

Strategy Aligned Toward Shareholder Value Capital Management * (Underwriting Margin + Return on Invested Assets)=Shareholder Value Sustainable competitive advantages • Successfully operating in niche markets and attractive • Continued product innovation geographies • Superior customer service across platform • Underwriting expertise with a focus on risk selection • Industry leader in developing and leveraging digital platform Profitable organic and strategic growth • Profitable through underwriting cycles • Talented underwriting teams with proven track record • Disciplined M&A strategy • 7.1 point improvement in loss ratio from 2012 to 2016 Capital management a key driver in value creation • Strong track record of returning capital to shareholders • Practice total return investment strategies Deep, tenured and experienced management team • Senior leadership team averages more than 10 years at Argo and over 26 years of industry experience • CEO is the largest individual shareholder, with 3.45% beneficial ownership • Compensation structure for underwriters aligned with loss ratio performance Maximize Shareholder Value Creation Through Growth in Book Value per Share 4

Maximizing Shareholder Value - BVPS Growth Reported Book Value 2 Total Shareholder Return 1 Cumulative Dividends Price/Book 3 1 Year 28% 3 Year 49% 5 Year 117% Total 447% 9% CAGR (Incl. Dividends) 1.7x 1.6x 1.3x 1.2x 1.2x 1.2x 1.1x 1.1x 1.1x 1.1x 0.9x 0.9x 0.8x 0.8x 0.7x 0.7x 0.6x (1) Total shareholder return metrics as of the end of the most recent quarter. (2) Book value per common share: - Adjusted for June 2013, March 2015, June 2016 and March 2018 stock dividends - 2008-2011 restated to reflect adoption of ASU 2010-26 (related to accounting for costs associated with acquiring or renewing insurance contracts); 2007 and prior not restated - 2006 and prior years adjusted for PXRE merger - 2003-2006 includes impact of Series A Mandatory Convertible Preferred on an as-if-converted basis. Preferred stock fully converted into common shares as of Dec. 31, 2007 5 (2) Price/book represents the high for the YTD period

Evolution of Growth and Diversification Risk Management (sold renewal rights in 2005) International Operations U.S Operations 2002 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 BVPS $15.28 $17.78 $19.83 $21.89 $25.53 $29.50 $28.47 $33.78 $37.77 $36.32 $39.69 $42.37 $46.03 $47.22 $51.94 $53.46 51.43 Total Capital $328 $567 $717 $860 $992 $1,754 $1,763 $1,975 $1,986 $1,840 $1,915 $1,966 $2,025 $2,040 $2,160 $2,400 $2,327 (Millions) 2001 2005 2007 2008 - 2010 2011 - 2014 2016 - 2018 • Acquired Colony • Sold Risk • Completed • Acquired Lloyd’s • Established local • Acquired Ariel Re / and Rockwood Management acquisition in Syndicate 1200 presence in Syndicate 1910 business Bermuda Brazil, Singapore • Founded Trident • Established local • Acquired Italian and Shanghai (Public Entity) • Rebranded Argo presence in insurer Ariscom Group Dubai • Formed Argo Re * Excludes GWP recorded in runoff and corporate and other. 6 Note: BVPS (book value per common share) adjusted for June 2013, March 2015, June 2016 and March 2018 stock dividends.