Exhibit 99.1
A Differentiated Model with
Sustainable Advantage
Investor Presentation
June 3, 2008
Nasdaq: GLRE
This presentation includes statements about future economic performance, finances, expectations, plans and prospects of Greenlight Capital Re, Ltd. (“the Company”) that constitute forward-looking statements for purposes of the safe harbor provisions of the Private Securities Litigation Reform Act of 1995. Such forward-looking statements are subject to certain risks and uncertainties that could cause actual results to differ materially from those suggested by such statements.
For further information regarding cautionary statements and factors affecting future results, please refer to the Company’s most recent Annual Report on Form 10-K, the Quarterly Report on Form 10-Q filed subsequent to the Annual Report and other documents filed by the Company with the SEC. The Company undertakes no obligation to update or revise publicly any forward-looking statement whether as a result of new information, future developments or otherwise. All information as of March 31, 2008 unless otherwise noted.
2
Short formal presentations, followed by Q&A and a reception
Today’s Agenda
John Andre, Group V.P. A.M. Best – Industry Overview and Rating Process
Len Goldberg, CEO – Background and Vision
Bart Hedges, President and CUO – Underwriting Philosophy and Examples
David Einhorn, Chairman – Investment Review/Preview
Tim Courtis, CFO – Capital and Risk Management
Q&A and Reception
Best’s Perspectives on Reinsurance and
Bermuda Segment
Capacity readily available in nearly all markets
High cedant retentions, capital market solutions and
government actions reduce demand
New entrants and incumbent diversification change
competitive landscape
Bermudan reinsurers expand scope through U.S. E&S
markets and Lloyd’s Syndicates
3
Review of Reinsurance and Bermuda
Segment - continued
Enterprise Risk Management fully embraced
Improved modeling tools enable reinsurers to garner
appropriate rates relative to exposures
Capital management-extensive share repurchase and
increased dividend pay-outs
Subprime impact modest with some exceptions
4
Review of Reinsurance and Bermuda
Segment - continued
Harder to generate adequate risk-adjusted returns
relative to capital at risk
Moderate M&A Activity-no blockbusters
Capital market solutions broadly accepted
5
Preview of Reinsurance and Bermuda
Segment - continued
Anticipating another profitable 2008
Pressure on margins intensifies
Wild-card is catastrophes
Double-digit rate decreases at Jan 1 renewals
Capital & risk management even more critical
Acquisitions likely as growth is hard to come by
6
Financial Trends-Bermuda Insurance
and Reinsurance
2005
(1)
2006
2007
2008P
Net Premiums Written Growth %
5.4
3.2
0.8
3.0
Loss & LAE Ratio
92.8
55.7
54.9
65.0
Underwriting Expense Ratio
26.5
28.3
28.0
28.0
Combined Ratio
119.3
84.1
82.9
93.0
Less: Loss Reserve Development
(1.0)
(2.2)
(5.2)
(2.5)
AY Combined Ratio (Normalized)
120.3
86.3
88.2
95.5
Change in Equity %
5.6
40.7
14.4
3.8
Return on Equity %
(7.0)
17.2
15.9
12.4
7
(1) Excludes Class of 2005 Source: A.M. Best
Best’s Rating Perspective – Bringing it
all Together
Capital strength is the foundation
Sustained, stable operating profitability ensures
future strength
Well-diversified, strong business profile ensures
stability
Depth, experience and stability of management
influences profile
8
9
Why Greenlight Re?
Differentiated, symmetric approach
Low leverage model with significant upside potential
A- rating from A.M. Best with ability to invest 100%
in equities
Proven underwriting and investment capabilities
Uniquely positioned for current market conditions
= Sustainable Advantage
Managing Our Business
10
11
We are a Cayman Islands specialty property and casualty reinsurer
with a differentiated reinsurance and investment strategy
Greenlight Re Vision
Capitalize on inefficiencies in the traditional approach to
reinsurance
Generate superior underwriting economics
Derive superior returns from both sides of the balance sheet
Maintain a highly skilled and focused team
Align long-term management and shareholder interests
Focus on long-term growth in book value per share
12
Greenlight Re Model
Focus on downside on a deal-
by-deal basis
Fewer, bigger deals that are
important to our clients and us
Focus on deal economics
Bottom-up approach to
underwriting portfolio
Portfolio is sum total of good
opportunities
Small team of highly skilled
generalists
Capital preservation on
investment-by-investment basis
Concentrate on best
investment ideas
Focus on business economics
Bottom-up approach to
investment selection
Portfolio is sum total of good
opportunities
Small team of highly skilled
generalists
Liability
Asset
DELIVER SUPERIOR LONG-TERM GROWTH IN BOOK VALUE
A fundamentally different, symmetric approach to the reinsurance business
13
Cyclical Opportunities
Source: National Association of Insurance Commissioners (NAIC) Annual Statement Database.
Casualty Excess Reinsurance
80.0%
100.0%
120.0%
Combined
Ratio
140.0%
160.0%
180.0%
200.0%
Current Estimate
Initial Estimate
14
Underwriting Philosophy
Lead underwriter for majority of transactions
Generalists with flexibility to look at a wide range of
opportunities
Rigorous modeling combined with practical underwriting
experience
Each contract stands on its own
Incorporate risk-aversion into pricing
Focus on transaction economics rather than on earnings or
premium growth
Cradle-to-grave underwriting and administration process
15
Select contracts which offer superior economic returns
Concentrate on underserved/dislocated markets with unique
needs
Focus on strategic relationships rather than price driven or
commodity buyers
Frequency business orientation; severity business more
opportunistic
Generalist team approach with client access to decision
makers
Service both global and Cayman markets
Underwriting Opportunities
Our Underwriters
16
17
Specialist underwriter requires rated reinsurer for program
$20 million in annual premium, maximum loss of $1 million on any
one event (frequency business)
Client wants to share risk with us
Client values underwriting results and is willing to give up float
Solution:
We reinsure 100% of the business and then share underwriting
results with a Cayman captive owned by the specialist
underwriter
We keep the float (we share economic risk, not cash flows)
which also acts as collateral
Underwriting Strategy: An Attractive Deal
18
Company requires $100 million protection against severity losses
The level of protection required has never been breached, and
models show it is a 1-in-100 year event
Client shares little/no risk once our cover is breached
Company offers $5 million of premium
Result:
The market accepts this deal and 10 different reinsurers
participate, but not Greenlight Re
Significant model uncertainty, enormous downside risk, non-
lead position, commoditized
Underwriting Strategy: Taking a Pass
19
Investment Approach
Portfolio managed exclusively by DME Advisors, an affiliate of
Greenlight Capital
Value-oriented strategy
Primarily long/short publicly-traded equity and corporate debt
securities
Lower volatility than equity indices
Limited leverage
Investment program matched to Greenlight Re’s goals
Maximize total risk-adjusted return with focus on capital
preservation
Direct claim on assets
14.6% annualized return (net of fees) from August 2004 through
May 2008
20
Investment Portfolio Summary
Data since IPO (13 months May 2007 - May 2008):
Performance
Average
GLRE
S&P 500
(gross)
Exposure
Annualized Return
12.9%
-3.4%
Long
-0.9%
90%
Annualized Std. Dev
8.5%
11.5%
Short
18.0%
-53%
Current Top 5 Long Positions
Current Position Concentration
Ameriprise Financial, Inc
Long
Short
Arkema
Top 5
36%
22%
Criteria Caixa Corp
Top 10
55%
31%
Microsoft Corporation
Target Corp
Exposure
97%
-52%
Current Investment Environment
21
22
Current Investment Environment
Credit crisis still playing out
Defensively positioned
Long unlevered companies at low absolute valuations
with strong market positions and/or internal restructuring
opportunities
Short credit sensitive financials and companies at high
multiples of earnings estimates that assume a second-
half recovery
Don’t be a hero
23
Compensation Framework
Align management and shareholders
Compensate for true increase in economic value, not for
premium growth, GAAP accounting, irrational
exuberance or “fully deploying capital”
Cash Bonus Program:
Track economics of every contract individually
No bonus when underwriting ROE less than Risk Free return
Target Bonus when ROE = target ROE
Uncapped upside when ROE in excess of target
First bonus payment after three years with continuous roll-forward
So far, so good
24
Risk and Capital Management
2007 premium to capital ratio of 0.2, anticipated to
increase as portfolio develops
Low leverage play:
No corporate debt
Low premium-to-capital and reserve-to-capital ratios
Frequency business orientation
CEO and CFO review reserves by account every quarter
Proposal to amend Company’s Articles of Association to
allow flexibility for share repurchases
($10)
$15
$40
Millions
$65
$90
$115
$140
Quarter ended
Cumulative net UW profit
Cumulative net UW profit plus risk free inv. income
Cumulative Actual net income
25
Contributions to Retained Earnings
26
NA
NA
221.0
99.0%
Book Value Growth
$ in millions
Notes:
1. The Composite Ratio is the ratio of underwriting losses incurred and acquisition costs, excluding internal expenses, to premiums earned.
2. The Combined Ratio is the sum of the loss ratio, acquisition cost ratio and the internal expense ratio.
3. 2004 and 2005 have been adjusted for principal outstanding on a promissory note which was fully repaid in 2006.
$ per share
NA
NA
248.0
98.6%
75.5
109.6
312.2
105.9%
Composite Ratio1
Combined Ratio2
Capital and Surplus3
Invested Assets/Capital
80.0
92.2
605.6
110.0%
14.6% CAGR in fully diluted book value per share since inception
80.2
96.4
600.1
111.7%
$(4.8)
$35.3
$57.0
$26.3
$6.8
$10.40
$11.63
$14.27
$16.57
$16.40
(20.0)
0.0
20.0
Net Income
40.0
60.0
80.0
100.0
2004
2005
2006
2007
1Q 2008
$0.00
$4.00
$8.00
BVPS
$12.00
$16.00
$20.00
Net Income
Basic Adjusted Book Value per Share
Net Invested Assets
$0
$50
$100
$150
$200
$250
$300
$350
$400
$450
$500
$550
$600
$650
$700
Millions
Quarter ended
Capital
Capital + Retained Earnings
Capital + Retained Earnings + Float
27
Current ROE Sensitivity
Assumptions:
Earned Premium = 20% of capital
Invested Assets = 120% of capital
Combined Ratio (%)
80.0
90.0
100.0
110.0
120.0
5.0
10
8
6
4
2
10.0
16
14
12
10
8
15.0
22
20
18
16
14
20.0
28
26
24
22
20
Investment
Return
(%)
25.0
34
32
30
28
26
28
Combined Ratio (%)
80.0
90.0
100.0
110.0
120.0
5.0
24
16
9
1
(6)
10.0
33
25
18
10
3
15.0
41
34
26
19
11
20.0
50
43
35
28
20
Investment
Return
(%)
25.0
59
51
44
36
29
29
Hypothetical ROE Sensitivity
Assumptions:
Earned Premium = 75% of capital
Invested Assets = 175% of capital
30
Why Greenlight Re?
Differentiated, symmetric approach
Low leverage model with significant upside potential
A- rating from A.M. Best with ability to invest 100% in
equities
Proven underwriting and investment capabilities
Uniquely positioned for current market conditions
= Sustainable Advantage
31
Q&A
###
Forward-Looking Statements
This news release contains forward-looking statements within the meaning of the U.S. federal securities laws. We intend these forward-looking statements to be covered by the safe harbor provisions for forward-looking statements in the U.S. Federal securities laws. These statements involve risks and uncertainties that could cause actual results to differ materially from those contained in forward-looking statements made on behalf of the Company. These risks and uncertainties include the impact of general economic conditions and conditions affecting the insurance and reinsurance industry, the adequacy of our reserves, our ability to assess underwriting risk, trends in rates for property and casualty insurance and reinsurance, competition, investment market fluctuations, trends in insured and paid losses, catastrophes, regulatory and legal uncertainties and other factors described in our annual report on Form 10-K filed with the Securities Exchange Commission. The Company undertakes no obligation to publicly update or revise any forward-looking statements, whether as a result of new information, future events or otherwise.
About Greenlight Capital Re, Ltd.
Greenlight Re (www.greenlightre.ky) is a specialty property and casualty reinsurance company based in the Cayman Islands. The Company provides a variety of custom-tailored reinsurance solutions to the insurance, risk retention group, captive and financial marketplaces. Established in 2004, Greenlight Re selectively offers customized reinsurance solutions in markets where capacity and alternatives are limited. With a focus on deriving superior returns from both sides of the balance sheet, Greenlight Re’s assets are managed according to a value-oriented equity-focused strategy that complements the Company’s business goal of long-term growth in book value per share.
Contact:
Alex Stanton
Stanton Crenshaw Communications
(212) 780-1900
alex@stantoncrenshaw.com