Pma Capital 8K Oppenheimer 4th Annual Mid and Small Cap Conference | PMACA 14 Nov 08

Exhibit 99.1

Oppenheimer 4th Annual Mid and Small Cap
Conference

November 18, 2008

Forward-looking
statements

q This presentation and our discussion contain forward-
looking information and statements including, but not
limited to, such matters as business strategies, market
trends, future financial performance, and other matters
which inherently involve risks and uncertainties which could
cause actual results to differ from those projected or
implied in the forward-looking statements. Please refer to
the Company’s SEC filings including its most recent Annual
Report on Form 10-K for risk factors which could cause
actual performance to differ from these forward-looking
statements.

Who We Are

Two Ongoing Operating Segments

The PMA Insurance Group

q Solid presence in workers’ compensation market

q Disciplined underwriting standards

q Superior long-term client relationships

q Statutory capital of $336 million

Fee-based Business

q Includes combined operating results of PMA Management Corp., PMA
Management Corp. of New England and Midlands Management
Corporation

q Acquisition of Midlands in October 2007 provides expanded fee-
based services and customer base

q In June 2008, acquired a workers’ compensation TPA in Connecticut,
a market we previously had little penetration

Run-off Operations- Sale agreement executed in 2008, pending state
approval

____________________

* Based on direct premiums written, excludes fronting premiums.

36%

10%

12%

PMA has 50 state writing and servicing capabilities

Highlights

q 2008 Focus:

§ Profitable, measured growth at Primary
Insurance Operations

§ High client retention and expansion of Fee-
based Business opportunities, as demonstrated
by high rate of organic growth and June 2008
acquisition

§ Assist with regulatory review process in order
to obtain approval to close on sale of Run-off
Operations

($ millions, except per share)	2008	2007
Direct premiums written	$387.7	$418.3
Net premiums earned	286.5	284.6
Fee-based revenues	50.1	22.8
Operating income from continuing operations	18.0	11.6
Loss from discontinued operations	(4.9)	(16.5)
After Tax Capital Gains (Losses)	(3.2)	-
Net Income (Loss)	$9.8	$(5.0)
Earnings per share from continuing operations	$.46	$.35
Loss per share from discontinued operations	(.15)	(.50)
Earnings (Loss) per share	$.31	$(.15)

Consolidated
Year to Date 9/30 Results

Consolidated
Nine Month Results

q Improved underwriting results at The PMA
Insurance Group (combined ratio 96.5% vs.
99.0% in 2007)

q Pre-tax operating income increased by 26% at
The PMA Insurance Group, compared to first nine
months of 2007

q Fee-based revenues increased $27.3 million to
$50.1 million due to acquisition of Midlands and
organic growth at PMA Management Corp.

The PMA Insurance Group

Business Overview

q Specializes in workers’ compensation and other
commercial lines

q Focus on mid-size to large accounts

§ Commercial Markets

§ Risk Management Services

§ Specialty Markets

q Reputation for excellent customer service and
execution

Premium Distribution by Class

All Lines Combined*

* Excluding Fronting Premiums

Diversified Distribution Channels

Premium Profile by Source*

FY 2007

Q3 2008

* Excluding Fronting Premiums

Source: AM Best

Proven Platform

q Disciplined underwriting -> Consistent operating returns

q The PMA Insurance Group - Workers’ Compensation
Estimated Undiscounted Accident Year Net Loss and LAE
Ratio (2003 adjusted for retro premium)

Maintain Competitive Advantage
in Workers’ Compensation Line

q Long-term strategy of Insurance Group is to write workers
compensation business at a combined ratio of 100% through
underwriting cycle

q September year to date 2008 combined ratio of 96.5%, 2007
full year combined ratio was 99.7%

q Measured steps to improve expense ratio, while maintaining
service levels to customers

q Expense target is currently to maintain controllable expense
growth less than half the rate of direct premium growth

q Claims Strategic Alliances assist in managing loss costs

§ Medical networks

§ Bill review

§ Catastrophic claims

Managing the Loss and
LAE Ratio

q Pricing changes, coupled with payroll inflation for rate sensitive
workers’ compensation business were below overall estimated loss
trends

q Diversification among classes of business insured

q Loss containment protection in loss sensitive business (about 40-
45% of our business) reduce risk to Company

q Outcome focused claims philosophy

§ Full integration of nurse professionals in claims process

§ In-house counsel in select jurisdictions

Managing the Loss and
LAE Ratio (cont.)

q Strategic alliances:

§ Coventry: preferred provider network; out of network
bill review

§ QualCare: preferred provider network in NJ

§ MedRisk: physical therapy provider

§ Corporate Systems: detailed medical bill review

§ TMESYS: retail pharmacy program

§ Paradigm: catastrophic claim management

§ Computer Sciences Corporation: legal bill review

Fee-based Business

q In fourth quarter of 2007, began reporting Fee-based Business
results as a separate operating segment

q PMA Management Corp.

§ Third-Party Administrator (TPA) producing fee-based revenues

§ Focus on workers’ compensation & risk management services

§ Business shares IT infrastructure with PMA Insurance Group

q Midlands Management Corporation

§ Acquired October 1, 2007

§ Oklahoma City-based managing general agent (MGA), program
administrator and provider of TPA services

§ Little overlap with PMA Management Corp.

q In June 2008, acquired PMA Management Corp. of New England
(formerly Webster Risk Services)

q Revenues and margins from our fee-based businesses are less
volatile than insurance underwriting

PMA Management Corp.

q Broad service capabilities:

§ Claims administration/TPA

§ Managed care

§ Disability management

§ Risk control

q Solid portfolio of managed care strategic alliances
that leverage combined purchasing power with
insurance operations

q Three-year business retention of over 90%

q Revenue CAGR of over 16% since 2001 - continue
to see organic growth opportunities

Midlands Management
Corporation

q Acquired October 1, 2007- Initial cash paid of $19.8 million

§ Ultimate price, which is based on EBITDA growth levels
over next four years, could range from $22.8 million
(6.9x EBITDA) to $44.5 million (4.8x EBITDA)

q Overview of Midlands

§ Very strong name recognition and brand equity

§ TPA specializes in casualty claims adjusting

§ Managing general agency places excess workers’
compensation

§ Revenues in 2007 of $28 million

§ Will continue to operate in current markets with existing
management and will maintain its brand identity and
strong service culture

PMA Management Corp.
of New England

q Connecticut-based TPA, formerly Webster Risk
Services

q Purchase price of $7.3 million, closing adjustments
reduced cash transferred to $5.9 million

q Specializes in providing workers’ compensation
and risk management services to health care
systems and public entities

q Very little geographical overlap - expect to grow
New England annual revenue base of $6 million

q On an annual basis, expect to add 2 cents to
earnings- excludes any potential cross-selling

Holding Company Review

$ millions	9/30/08	12/31/07

Shareholders' Equity (Including SFAS #115)	$358.0	$378.6

Shareholders' Equity (Excluding SFAS #115)	$380.1	$374.6

Debt	$129.4	$131.3

Debt to Capital (Including SFAS #115)	27%	26%

Capitalization

$ millions		9/30/08

Trust Preferred and Surplus Notes, Mature 2033-37		$ 74.4
Monthly Senior Notes, Matures 2018		54.9
Other		.1
Total		$ 129.4

Debt Structure

Invested Assets

Total = $823 million

(excludes cash)

September 30, 2008

Asset Type

n Conservative investment
posture

n No wrapped ABS CDO
exposures

n No derivatives

n No equity exposure

n Pre-tax net unrealized loss
of $33 million at
September 30, 2008

n Outside professional
manager

Total = $735 million

(excludes short-term investments and cash)

September 30, 2008

Asset Quality

n AA+ average credit quality

n 68% AAA Rated or
Government bonds

n 2% held in Alternative A/
Subprime loans - average
credit quality of AAA with no
OTTI

n 4% held in credit-enhanced
securities with average credit
quality of AA- and imputed
credit quality of A

n Portfolio duration - 3.6 years

n Current portfolio book yield -
5.3%

pPre-tax other than temporary impairment (OTTI) charges of $8.2 million
and $913,000 taken through realized losses on holdings in Lehman senior
debt and Fannie Mae preferred stock, respectively; collectively approx 1% of
the investment portfolio. There were no other OTTI losses during the nine
month period ending September 30, 2008

pNo holdings in AIG or WaMu

pAlt A and Subprime portfolio, with a $17.9 million amortized book value,
continues to pay down; collected $10.7 million in principal paydowns since
March 2007

pNo delinquencies or OTTI losses in the Alt A and Subprime portfolio

pHeld CMO’s with an amortized book value of $181.8 million issued by
entities other than Government Sponsored Enterprises. These securities had
a weighted average life of 5.2 years, an average credit quality of AAA and
were paying down as expected; delinquencies were well below their credit
support structure and no defaults.

pDetailed portfolio holdings at September 30, 2008 and December 31, 2007
posted on our website (www.pmacapital.com)

Investment Portfolio
Comments- 9/30/08

1 Fee-based Business book value increased $0.23 as a result of the acquisition of
PMA Management Corp. of New England. The purchase price was funded by the
Holding Company.

PMA Capital
Book Value

q 2008 results through September detail execution of our
business plan:

§ Measured revenue growth at The PMA Insurance Group

§ Diligent expense management

§ Continued expansion of fee-based service platform

q Expecting profitable growth in workers’ compensation in
2008

q Execution of 2008 plan should result in continued
improvement in profitability of operations

q Expect a return on equity of between 5.5% and 6.5% on
our ongoing businesses in 2008

q September 30, 2008 book value of $11.20 per share,
compared to a current stock price (November 12) of $5.02

Pma Capital (PMACA) Inactive 8-KOppenheimer 4th Annual Mid and Small Cap Conference