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UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
FORM 10-Q
QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934
For the quarterly period ended June 30, 2022
Commission File Number 001-33289
https://cdn.kscope.io/445635761414a66fdc86c42f353ffe52-esgr-20220630_g1.jpg
ENSTAR GROUP LIMITED
(Exact name of Registrant as specified in its charter)
BERMUDAN/A
(State or other jurisdiction of incorporation or organization)(I.R.S. Employer Identification No.)
Windsor Place, 3rd Floor, 22 Queen Street, Hamilton HM JX, Bermuda
(Address of principal executive offices, including zip code)
Registrant’s telephone number, including area code: (441292-3645
Securities registered pursuant to Section 12(b) of the Act:
Title of Each ClassTrading Symbol(s)Name of Each Exchange on Which Registered
Ordinary shares, par value $1.00 per shareESGRThe NASDAQ Stock MarketLLC
Depositary Shares, Each Representing a 1/1,000th Interest in a 7.00% ESGRPThe NASDAQ Stock MarketLLC
Fixed-to-Floating Rate Perpetual Non-Cumulative Preferred Share, Series D, Par Value $1.00 Per Share
Depositary Shares, Each Representing a 1/1,000th Interest in a 7.00%ESGROThe NASDAQ Stock MarketLLC
Perpetual Non-Cumulative Preferred Share, Series E, Par Value $1.00 Per Share
Indicate by check mark whether the registrant (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days.    Yes     No 
Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T during the preceding 12 months (or for such shorter period that the registrant was required to submit such files).    Yes No 
Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company” and "emerging growth company" in Rule 12b-2 of the Exchange Act.
Large accelerated filer
Accelerated filer¨Non-accelerated filer¨Smaller reporting companyEmerging growth company
If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act.
Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act).    Yes      No  
As at August 8, 2022, the registrant had outstanding 15,980,019 voting ordinary shares and 1,597,712 non-voting convertible ordinary shares, each par value $1.00 per share.
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Enstar Group Limited
Quarterly Report on Form 10-Q
For the Period Ended June 30, 2022
Table of Contents
 
  Page
PART I
Item 2.
Item 3.
Item 1.
Item 4.
PART II
Item 1.
Item 1A.
Item 2.
Item 3.
Item 4.
Item 5.
Item 6.
2

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GLOSSARY OF KEY TERMS
A&EAsbestos and environmental
Acquisition costsCosts that are directly related to the successful efforts of acquiring new insurance contracts or renewing existing insurance contracts, and which principally consist of incremental costs such as: commissions, brokerage expenses, premium taxes and other fees incurred at the time that a contract or policy is issued.
ADCAdverse development cover – A retrospective reinsurance arrangement that will insure losses in excess of an established reserve and provide protection up to a contractually agreed amount.
Adjusted BVPS
Adjusted book value per ordinary share - Non-GAAP financial measure calculated by dividing Enstar ordinary shareholders’ equity, adjusted to add the proceeds from assumed exercise of warrants, by the number of ordinary shares outstanding, adjusted for the exercise of warrants and equity awards granted and not yet vested. See “Non-GAAP Financial Measures” in Part I, Item 2 for reconciliation.
Adjusted RLE
Adjusted run-off liability earnings - Non-GAAP financial measure calculated by dividing adjusted prior period development by average adjusted net loss reserves. See “Non-GAAP Financial Measures” in Part I, Item 2 for reconciliation.
Adjusted ROE
Adjusted return on equity - Non-GAAP financial measure calculated by dividing adjusted operating income (loss) attributable to Enstar ordinary shareholders by adjusted opening Enstar ordinary shareholders’ equity. See “Non-GAAP Financial Measures” in Part I, Item 2 for reconciliation.
Adjusted TIR
Adjusted total investment return - Non-GAAP financial measure calculated by dividing adjusted total investment return by average adjusted total investable assets. See “Non-GAAP Financial Measures” in Part I, Item 2 for reconciliation.
AFSAvailable-for-sale
AmTrustAmTrust Financial Services, Inc.
Annualized
Calculation of the quarterly result or year-to-date result multiplied by four and then divided by the number of quarters elapsed within the applicable year-to-date period.
AOCI
Accumulated other comprehensive income
ArdenArden Reinsurance Company Ltd.
Atrium
Atrium Underwriting Group Limited
BMABermuda Monetary Authority
BSCRBermuda Solvency Capital Requirement
BVPSBook value per ordinary share - GAAP financial measure calculated by dividing Enstar ordinary shareholders’ equity by the number of ordinary shares outstanding.
CitcoCitco III Limited
CLOCollateralized loan obligation
Core SpecialtyCore Specialty Insurance Holdings, Inc.
DCoDCo LLC
Defendant A&E liabilities
Defendant asbestos and environmental liabilities - Non-insurance liabilities relating to amounts for indemnity and defense costs for pending and future claims, as well as amounts for environmental liabilities associated with properties.
DCA
Deferred charge asset - The amount by which estimated ultimate losses payable exceed the premium consideration received at the inception of a retroactive reinsurance agreement and that are subsequently amortized over the estimated loss settlement period.
Dowling FundsDowling Capital Partners I, L.P. and Capital City Partners LLC
EB Trust
Enstar Group Limited Employee Benefit Trust
Enhanzed ReEnhanzed Reinsurance Ltd.
EnstarEnstar Group Limited and its consolidated subsidiaries
Enstar FinanceEnstar Finance LLC
Exchange TransactionThe exchange of a portion of our indirect interest in Northshore for all of the Trident V Funds’ indirect interest in StarStone U.S.
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GLOSSARY OF KEY TERMS
FALFunds at Lloyd's - A deposit in the form of cash, securities, letters of credit or other approved capital instrument that satisfies the capital requirement to support the Lloyd's syndicate underwriting capacity.
Funds heldThe account created with premium due to the reinsurer pursuant to the reinsurance agreement, the balance of which is credited with investment income and losses paid are deducted.
Funds held by reinsured companies
Funds held, as described above, where we receive a fixed crediting rate of return or other contractually agreed return on the assets held.
Funds held - directly managed
Funds held, as described above, where we receive the actual investment portfolio return on the assets held.
Future policyholder benefits
The liability relating to life reinsurance contracts, which are based on the present value of anticipated future cash flows and mortality rates.
Gate or side-pocket
A gate is the ability to deny or delay a redemption request, whereas a side-pocket is a designated account for which the investor loses its redemption rights.
Hillhouse Group
Hillhouse Capital Management, Ltd. and Hillhouse Capital Advisors, Ltd.
IBNR
Incurred but not reported - The estimated liability for unreported claims that have been incurred, as well as estimates for the possibility that reported claims may settle for amounts that differ from the established case reserves as well as the potential for closed claims to re-open. These provisions are shown net of reinsurance balances recoverable.
InRe FundInRe Fund, L.P.
Investable assetsThe sum of total investments, cash and cash equivalents, restricted cash and cash equivalents and funds held
JSOP
Joint Share Ownership Plan
LAELoss adjustment expenses
Lloyd'sThis term may refer to either the society of individual and corporate underwriting members that pool and spread risks as members of one or more syndicates, or the Corporation of Lloyd’s, which regulates and provides support services to the Lloyd’s market
LPTLoss Portfolio Transfer - Retroactive reinsurance transaction in which loss obligations that are already incurred are ceded to a reinsurer, subject to any stipulated limits
Monument ReMonument Insurance Group Limited
Morse TEC Morse TEC LLC
NAVNet asset value
NCI
Noncontrolling interests
New businessMaterial transactions, other than business acquisitions, which generally take the form of reinsurance or direct business transfers.
NorthshoreNorthshore Holdings Limited
OLROutstanding loss reserves - Provisions for claims that have been reported and accrued but are unpaid at the balance sheet date.
Parent Company
Enstar Group Limited, excluding its consolidated subsidiaries
Policy buy-backSimilar to a commutation, for direct insurance contracts
pp
Percentage point(s)
PPDPrior period development - Changes to loss estimates recognized in the current calendar year that relate to loss reserves established in previous calendar years.
Private equity fundsInvestments in limited partnerships and limited liability companies
Q2
Second quarter
QTD
Quarter-to-date
Reinsurance to close (RITC)A business transaction to transfer estimated future liabilities attached to a given year of account of a Lloyd's syndicate into a later year of account of either the same or different Lloyd's syndicate in return for a premium.
Reserves for losses and LAEManagement's best estimate of the ultimate cost of settling losses as of the balance sheet date. This includes OLR and IBNR.
Retroactive reinsuranceContracts that provide indemnification for losses and LAE with respect to past loss events.
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GLOSSARY OF KEY TERMS
RLERun-off liability earnings – GAAP-based financial measure calculated by dividing prior period development by average net loss reserves.
RNCI
Redeemable noncontrolling interests
ROEReturn on equity - GAAP-based financial measure calculated by dividing net earnings (loss) attributable to Enstar ordinary shareholders by opening Enstar ordinary shareholders’ equity
Run-offA line of business that has been classified as discontinued by the insurer that initially underwrote the given risk
Run-off portfolioA group of insurance policies classified as run-off.
SECU.S. Securities and Exchange Commission
SGL No. 1SGL No. 1 Limited
SSHLStarStone Specialty Holdings Limited
StarStone InternationalStarStone's non-U.S. operations
StarStone U.S.StarStone U.S. Holdings, Inc. and its subsidiaries
Step Acquisition
The purchase of the entire equity interest in Enhanzed Re held by an affiliate of Hillhouse Capital Management Ltd and Hillhouse Capital Advisors, Ltd.
Stone PointStone Point Capital LLC
SULStarStone Underwriting Limited
TIRTotal investment return - GAAP financial measure calculated by dividing total investment return recognized in earnings for the applicable period by average total investable assets
Trident V FundsTrident V, L.P., Trident V Parallel Fund, L.P. and Trident V Professionals Fund, L.P.
U.S. GAAPAccounting principles generally accepted in the United States of America
ULAEUnallocated loss adjustment expenses - Loss adjustment expenses relating to run-off costs for the estimated payout of the run-off, such as internal claim management or associated operational support costs.
Unearned premium
The unexpired portion of policy premiums that will be earned over the remaining term of the insurance contract.
VIEVariable interest entities
YTD
Year-to-date
2021 Repurchase Program
An ordinary share repurchase program adopted by our Board of Directors on November 29, 2021, for the purpose of repurchasing a limited number of our ordinary shares, not to exceed $100 million in aggregate. This plan was fully utilized in April 2022.
2022 Repurchase Program
An ordinary share repurchase program authorized by our Board of Directors on May 5, 2022, which is effective through May 5, 2023. Under this program, we may repurchase a limited number of our ordinary shares, not to exceed $200 million in aggregate.
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CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS
This quarterly report and the documents incorporated by reference herein contain statements that constitute "forward-looking statements" within the meaning of Section 21E of the Securities Exchange Act of 1934, as amended, or the Exchange Act, with respect to our financial condition, results of operations, business strategies, operating efficiencies, competitive positions, growth opportunities, plans and objectives of our management, as well as the markets for our securities and the insurance and reinsurance sectors in general.
Statements that include words such as "estimate," "project," "plan," "intend," "expect," "anticipate," "believe," "would," "should," "could," "seek," "may" and similar statements of a future or forward-looking nature identify forward-looking statements for purposes of the federal securities laws or otherwise.
All forward-looking statements are necessarily estimates or expectations, and not statements of historical fact, reflecting the best judgment of our management and involve a number of risks and uncertainties that could cause actual results to differ materially from those suggested by the forward-looking statements.
These forward looking statements should, therefore, be considered in light of various important factors, including those set forth in this report and in our Annual Report on Form 10-K for the year ended December 31, 2021, which could cause actual results to differ materially from those suggested by the forward-looking statements. These factors include:
the adequacy of our loss reserves and the need to adjust such reserves as claims develop over time, including due to the impact of emerging claim and coverage issues and disputes that could impact reserve adequacy;
our acquisitions, including our ability to evaluate opportunities, successfully price acquisitions, address operational challenges, support our planned growth and assimilate acquired portfolios and companies into our internal control system in order to maintain effective internal controls, provide reliable financial reports and prevent fraud;
increased competitive pressures, including increased competition in the market for run-off business;
our ability to obtain regulatory approvals, including the timing, terms and conditions of any such approvals, and to satisfy other closing conditions in connection with our acquisition agreements, which could affect our ability to complete acquisitions;
Enhanzed Re’s life and annuity business, including the performance of assets to support the liabilities, the risk of mismatch in asset/liability duration and assumptions used to estimate reserves for future policy benefits proving to be inaccurate;
the variability of statutory capital requirements and the risk that we may require additional capital in the future, which may not be available or may be available only on unfavorable terms;
our reinsurance subsidiaries may not be able to provide the required collateral to ceding companies pursuant to their reinsurance contracts, including through the use of letters of credit;
the availability and collectability of our ceded reinsurance;
the ability of our subsidiaries to distribute funds to us and the resulting impact on our liquidity;
losses due to foreign currency exchange rate fluctuations;
climate change and its potential impact on the returns from our run-off business and our investments;
the value of our investment portfolios and the investment income that we receive from these portfolios may decline materially as a result of market fluctuations and economic conditions, including those related to interest rates, credit spreads and equity prices;
the effects of inflation, including its impact on our loss cost trends and operating expenses, and the effects of global economic policy responses to inflation, such as increasing interest rates and their impact on our investment portfolio;
our ability to structure our investments in a manner that recognizes our liquidity needs;
our strategic investments in alternative asset classes and joint ventures, which are illiquid and may be volatile;
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CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS
our ability to accurately value our investments, which requires methodologies, estimates and assumptions that can be highly subjective, and the inaccuracy of which could adversely affect our financial condition;
the complex regulatory environment in which we operate, including that ongoing or future industry regulatory developments will disrupt our business, affect the ability of our subsidiaries to operate in the ordinary course or to make distributions to us, or mandate changes in industry practices in ways that increase our costs, decrease our revenues or require us to alter aspects of the way we do business;
loss of key personnel;
operational risks, including cybersecurity events, external hazards, human failures or other difficulties with our information technology systems that could disrupt our business or result in the loss of critical and confidential information, increased costs;
tax, regulatory or legal restrictions or limitations applicable to us or the (re)insurance business generally;
changes in tax laws or regulations applicable to us or our subsidiaries, or the risk that we or one of our non-U.S. subsidiaries become subject to significant, or significantly increased, income taxes in the United States or elsewhere; and
the ownership of our shares resulting from certain provisions of our bye-laws and our status as a Bermuda company.
The factors listed above should not be construed as exhaustive and should be read in conjunction with the Risk Factors that are included in our Annual Report on Form 10-K for the year ended December 31, 2021. We undertake no obligation to publicly update or review any forward looking statement, whether to reflect any change in our expectations with regard thereto, or as a result of new information, future developments or otherwise, except as required by law.
7

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PART I — FINANCIAL INFORMATION
ITEM 2. MANAGEMENT’S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS
Unless the context indicates otherwise, the terms "Enstar," "we," "us" or "our" mean Enstar Group Limited and its consolidated subsidiaries.
The following discussion and analysis of our financial condition as of June 30, 2022 and our results of operations for the three and six months ended June 30, 2022 and 2021 should be read in conjunction with our unaudited condensed consolidated financial statements and the related notes included elsewhere in this quarterly report and the audited consolidated financial statements and notes thereto contained in our Annual Report on Form 10-K for the year ended December 31, 2021.
Some of the information contained in this discussion and analysis or included elsewhere in this quarterly report, including information with respect to our plans and strategy for our business, includes forward-looking statements that involve risks, uncertainties and assumptions. Our actual results and the timing of events could differ materially from those anticipated by these forward-looking statements as a result of many factors, including those discussed under "Cautionary Statement Regarding Forward-Looking Statements" and Item 1A of our Annual Report on Form 10-K for the year ended December 31, 2021.
Table of Contents
SectionPage
Consolidated Results of Operations — for the Three and Six Months Ended June 30, 2022 and 2021
Results of Operations by Segment — for the Three and Six Months Ended June 30, 2022 and 2021
Enstar Group Limited | Second Quarter 2022 | Form 10-Q                 8

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations
Operational Highlights
Our consolidated results reflect our continued progress on providing capital release solutions to our clients by acquiring and managing their run-off portfolios.
Operational highlights for the six months ended June 30, 2022 include:
Assumed $3.1 billion of loss reserves from Run-off Transactions
On May 20, 2022 we completed an LPT transaction with Aspen Insurance Holdings Limited (“Aspen”) with respect to $3.1 billion of net loss reserves, subject to a limit of $3.6 billion. An existing ADC between Aspen and us that closed in June 2020 was absorbed into this LPT.
As a result of this LPT transaction, we assumed an incremental $1.9 billion of net loss reserves with a diverse mix of property, liability and specialty lines of business, in exchange for incremental premium of $1.9 billion,1 and assumed claims control.
Executed Capital Transactions
We completed a $500 million junior subordinated notes offering in January 2022, the net proceeds of which were primarily used to fund the payment at maturity of the outstanding $280 million aggregate principal amount of our senior notes, which matured in March 2022.
We repurchased 697,580 voting ordinary shares during the six months ended June 30, 2022 for an aggregate $163 million, representing an average price per share of $233.92 and a weighted average discount to our net book value per ordinary share of 20.3%. During the six months ended June 30, 2022, we utilized $105 million of the $200 million authorized under the 2022 Repurchase Program and the remaining $59 million authorized under the 2021 Repurchase Program to repurchase our ordinary shares.
1 Refer to “New Business” section for further details.
Enstar Group Limited | Second Quarter 2022 | Form 10-Q                 9

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations
Consolidated Results of Operations - For the Three and Six Months Ended June 30, 2022 and 2021
The following table sets forth our condensed consolidated statements of earnings:
 Three Months EndedSix Months Ended
June 30,$ / pp ChangeJune 30,$ / pp
Change
 2022202120222021
 (in millions of U.S. dollars, except per share data)
Underwriting Results
Net premiums earned$14 $59 $(45)$48 $152 $(104)
Net incurred losses and LAE
Current period (13)(50)37 (26)(104)78 
Prior period79 10 69 222 120 102 
Total net incurred losses and LAE66 (40)106 196 16 180 
Policyholder benefit expenses(6)— (6)(18)— (18)
Acquisition costs(12)(5)(7)(20)(39)19 
Investment Results
Net investment income106 76 30 186 138 48 
Net realized (losses) gains(38)(44)(75)(5)(70)
Net unrealized (losses) gains(591)400 (991)(972)390 (1,362)
Earnings (losses) from equity method investments(3)32 115 (83)
General and administrative expenses(83)(93)10 (168)(176)
NET (LOSS) EARNINGS ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS$(493)$378 $(871)$(775)$561 $(1,336)
GAAP measures:
Return on equity (“ROE”)(9.8)%6.0 %(15.8) pp(13.9)%9.1 %(23.0) pp
Annualized ROE(27.7)%18.2 %(45.9) pp
Annualized run-off liability earnings (“RLE”)3.7 %2.5 %1.2  pp
Annualized total investment return (“TIR”)(8.1)%6.8 %(14.9) pp
Non-GAAP measures:
Adjusted ROE*(2.9)%5.1 %(8.0) pp(4.2)%10.9 %(15.1) pp
Annualized Adjusted ROE*(8.4)%21.7 %(30.1) pp
Annualized Adjusted RLE *0.5 %1.1 %(0.6) pp
Annualized Adjusted TIR*(0.8)%8.0 %(8.8) pp
As of$ Change
June 30, 2022December 31, 2021
GAAP measure:
Book value per ordinary share (“BVPS”)$245.93 $316.34 $(70.41)
Non-GAAP measure:
Adjusted BVPS*$241.05 $310.80 $(69.75)
pp - Percentage point(s)
*Non-GAAP measure; refer to "Non-GAAP Financial Measures" section for reconciliation to the applicable GAAP financial measure.

Enstar Group Limited | Second Quarter 2022 | Form 10-Q                 10

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Item 2 | Management's Discussion and Analysis | Key Performance Measures
Overall Measures of Performance
BVPS and Adjusted BVPS*
https://cdn.kscope.io/445635761414a66fdc86c42f353ffe52-esgr-20220630_g2.jpg
BVPS and Adjusted BVPS* decreased by 22.3% and 22.4%, respectively, from December 31, 2021 to June 30, 2022, primarily due to recognized and unrecognized investment losses of $1.3 billion for the six months ended June 30, 2022.
ROE and Adjusted ROE*
https://cdn.kscope.io/445635761414a66fdc86c42f353ffe52-esgr-20220630_g3.jpg
Three and Six Months Ended June 30, 2022 versus 2021: ROE decreased by 15.8 and 23.0 pp for the three and six months ended June 30, 2022, respectively, primarily due to:
i.net realized and unrealized losses on other investments, including equities, for the three and six months ended June 30, 2022 compared to net gains in the comparative periods. This contributed 9.1 and 13.2 pp to the total reduction in ROE for the three and six months ended June 30, 2022, respectively;
ii.net realized and unrealized losses on fixed maturity securities for the three and six months ended June 30, 2022 compared to net gains and net losses for the three and six months ended June 30, 2021, respectively. This contributed 9.9 and 11.7 pp to the total reduction in ROE for the three and six months ended June 30, 2022, respectively;
iii.a reduction in earnings from equity method investments for the six months ended June 30, 2022 which contributed 1.3 pp to the total reduction in ROE for the six months ended June 30, 2022.
These negative factors were partially offset by:
iv. higher favorable PPD, which offset the reduction in ROE by 1.4 and 2.0 pp for the three and six months ended June 30, 2022, respectively; and
v.     higher net investment income, which offset the reduction in ROE by 0.9 and 1.1 pp for the three and six months ended June 30, 2022, respectively.
Adjusted ROE* decreased by 8.0 and 15.1 pp for the three and six months ended June 30, 2022, respectively, as it excludes the impact of net realized and unrealized losses on fixed maturity securities.
*Non-GAAP measure; refer to “Non-GAAP Financial Measures” section for reconciliation to the applicable GAAP financial measure.
Enstar Group Limited | Second Quarter 2022 | Form 10-Q                 11

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations
We discuss the results of our operations by aggregating certain captions from our condensed consolidated statement of earnings, as we believe it provides a more meaningful view of our results and eliminates repetition that would arise if captions were discussed on an individual basis.
In order to facilitate discussion, we have grouped the following captions:
Underwriting results: includes net premiums earned, net incurred losses and LAE, policyholder benefit expenses and acquisition costs.
Investment results: includes net investment income, net realized losses, net unrealized losses and earnings from equity method investments.
General and administrative results: includes general and administrative expenses.
Underwriting Results
Our strategy is focused on effectively managing portfolios and businesses in run-off. Although we have largely exited our active underwriting platforms, we still record net premiums earned and the associated current period net incurred losses and LAE and acquisition costs as a result of the run-off of unearned premiums from transactions completed in recent years.
Premiums earned in the Run-off segment are generally offset by the related current period net incurred losses and LAE and acquisition costs.
The components of underwriting results are as follows:
Three Months Ended June 30,
20222021
Run-offEnhanzed ReLegacy UnderwritingCorporate and otherTotalRun-offLegacy UnderwritingCorporate and otherTotal
(in millions of U.S. dollars)
Net premiums earned$$$$— $14 $42 $17 $— $59 
Net incurred losses and LAE:
Current period14 — (1)— 13 42 — 50 
Prior periods(121)— 37 (79)(59)46 (10)
Total net incurred losses and LAE(107)— 37 (66)(17)11 46 40 
Policyholder benefit expenses— — — — — — — 
Acquisition costs— — 12 — — 
Underwriting results$107 $(5)$(3)$(37)$62 $59 $$(46)$14 
Six Months Ended June 30,
20222021
Run-offEnhanzed ReLegacy UnderwritingCorporate and otherTotalRun-offLegacy UnderwritingCorporate and otherTotal
(in millions of U.S. dollars)
Net premiums earned$26 $15 $$— $48 $115 $37 $— $152 
Net incurred losses and LAE:
Current period25 — — 26 86 18 — 104 
Prior periods(171)(29)(26)(222)(98)(3)(19)(120)
Total net incurred losses and LAE(146)(29)(26)(196)(12)15 (19)(16)
Policyholder benefit expenses— 18 — — 18 — — — — 
Acquisition costs17 — — 20 29 10 — 39 
Underwriting results$155 $26 $(1)$26 $206 $98 $12 $19 $129 
Enstar Group Limited | Second Quarter 2022 | Form 10-Q                 12

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations
Current Period - Three and Six Months Ended June 30, 2022 and 2021
The current period underwriting results from our (re)insurance operations include net earned premiums that have been declining as we transition away from active underwriting activities.
The below charts are in millions of U.S. dollars.
https://cdn.kscope.io/445635761414a66fdc86c42f353ffe52-esgr-20220630_g4.jpg https://cdn.kscope.io/445635761414a66fdc86c42f353ffe52-esgr-20220630_g5.jpg
The reductions in net premiums earned and current period net incurred losses and LAE were driven by reduced levels of activity arising from our exit of our active underwriting platforms beginning in 2020.
We continue to earn premium from our StarStone International business and from our Enhanzed Re segment. In comparison, our 2021 earned premium was primarily driven by StarStone International and AmTrust reinsurance to close (“RITC”) business, which was entered into in 2019.
Prior Periods - RLE - Three Months Ended June 30, 2022 and 2021
The following tables summarize RLE % and Adjusted RLE %* by acquisition year, which management believes is useful in measuring and monitoring performance of our claims management activity on the portfolios that we have acquired. This permits comparability between acquisition years of different loss reserve volumes.
Three Months Ended June 30, 2022
RLE Adjusted RLE*
Acquisition YearPPDAverage net loss reservesAnnualized RLE %Adjusted PPD*Average adjusted net loss reserves*Annualized Adj RLE %*
(in millions of U.S. dollars)
2012 and prior$— $555 $$582 
2013(5)183 — 39 
201413 771 — 62 
2015288 — 274 
2016731 770 
201740 723 834 
201817 914 952 
2019(1)1,057 — 1,541 
2020 (1)
1,081 (1)1,049 
20213,964 17 4,380 
2022 (1)
— 1,333 1.9 %— 1,260 1.1 %
Total$79 $11,600 2.7 %$29 $11,743 1.0 %
(1) We have reclassified $2 million of PPD, $2 million of Adjusted PPD*, $393 million of average net loss reserves and $386 million of average adjusted net loss reserves* recorded in acquisition year 2020 arising from an ADC between Aspen and us to acquisition year 2022 to reflect the absorption of the ADC into the 2022 Aspen LPT transaction.
*Non-GAAP measure; refer to “Non-GAAP Financial Measures” section for reconciliation to the applicable GAAP financial measure.
Enstar Group Limited | Second Quarter 2022 | Form 10-Q                 13

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations
Three Months Ended June 30, 2022:
Our Annualized RLE % was positively impacted by a reduction of $48 million in the fair value of liabilities for which we have elected the fair value option in the 2017 and 2018 acquisition years as a result of increases in interest rates. Annualized RLE % was also positively impacted by favorable loss activity in our professional indemnity/directors and officers and workers’ compensation lines of business, most notably in the 2021 acquisition year. The favorable movements were partially offset by accelerated amortization of DCA.
Our Annualized Adjusted RLE %*, which excludes fair value adjustments, was positively impacted by the net reduction in estimates of net ultimate losses relating to the Run-off segment as described above.
Three Months Ended June 30, 2021
RLEAdjusted RLE*
Acquisition YearPPDAverage net loss reservesAnnualized RLE %Adjusted PPD*Average adjusted net loss reserves*Annualized Adj RLE %*
(in millions of U.S. dollars)
2012 and prior$$490 $$526 
2013(3)217 — 52 
2014980 77 
2015— 348 331 
2016831 871 
2017(13)1,010 1,023 
20181,239 1,233 
2019(4)1,177 1,665 
202012 1,851 1,800 
2021(10)1,882 (19)2,634 
Total$10 $10,025 0.4 %$24 $10,212 0.9 %
Three Months Ended June 30, 2021:
Our Annualized RLE % was positively impacted by favorable development in our professional indemnity/directors and officers line of business across our Lloyd’s portfolios relating to large claims on the 2012 and prior, 2016 and 2018 acquisition years and favorable actual versus expected loss experience in our workers’ compensation line of business on the 2017, 2020 and 2021 acquisition years.
This favorable development was partially offset by a $17 million increase in the fair value of liabilities for which we have elected the fair value option in the 2017 and 2018 acquisition years due to a decrease in interest rates. This adverse change is not included in the calculation of Adjusted PPD* or Annualized Adjusted RLE %*.
*Non-GAAP measure; refer to “Non-GAAP Financial Measures” section for reconciliation to the applicable GAAP financial measure.
Enstar Group Limited | Second Quarter 2022 | Form 10-Q                 14

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations
Prior Periods - RLE - Six Months Ended June 30, 2022 and 2021
The following tables summarize RLE % and Adjusted RLE %* by acquisition year:
Six Months Ended June 30, 2022
RLE Adjusted RLE*
Acquisition YearPPDAverage net loss reservesAnnualized RLE %Adjusted PPD*Average adjusted net loss reserves*Annualized Adj RLE %*
(in millions of U.S. dollars)
2012 and prior$$565 $$599 
2013(4)189 — 40 
201418 802 — 67 
2015292 — 277 
2016743 12 786 
2017118 785 856 
201842 958 985 
2019(8)1,075 (14)1,548 
2020 (1)
1,126 (6)1,093 
202149 4,029 20 4,452 
2022 (1)
— 1,333 1.9 %— 1,260 1.1 %
Total$222 $11,897 3.7 %$28 $11,963 0.5 %
(1) We have reclassified $2 million of PPD, $2 million of Adjusted PPD*, $393 million of average net loss reserves and $386 million of average adjusted net loss reserves* recorded in acquisition year 2020 arising from an ADC between Aspen and us to acquisition year 2022 to reflect the absorption of the ADC into the 2022 Aspen LPT transaction.
Six Months Ended June 30, 2022:
Our Annualized RLE % was positively impacted by a reduction of $146 million in the fair value of liabilities for which we have elected the fair value option in the 2017 and 2018 acquisition years as a result of increases in interest rates.
Annualized RLE % was also positively impacted by favorable loss activity on our professional indemnity/directors and officers and workers’ compensation lines of business, most notably in the 2021 acquisition year.
In addition, we experienced favorable claim activity on Enhanzed Re’s catastrophe book in the 2021 acquisition year.
Our Annualized Adjusted RLE %*, excludes fair value adjustments and changes in Enhanzed Re’s catastrophe loss liabilities.
Six Months Ended June 30, 2021
RLEAdjusted RLE*
Acquisition YearPPDAverage net loss reservesAnnualized RLE %Adjusted PPD*Average adjusted net loss reserves*Annualized Adj RLE %*
(in millions of U.S. dollars)
2012 and prior$$517 $$551 
2013143 — 58 
201413 999 17 83 
2015— 353 — 336 
2016839 881 
201753 1,050 1,031 
201827 1,269 18 1,246 
2019(3)1,192 1,687 
202023 1,902 14 1,849 
2021(10)1,426 (22)1,780 
Total$120 $9,690 2.5 %$50 $9,502 1.1 %
*Non-GAAP measure; refer to “Non-GAAP Financial Measures” section for reconciliation to the applicable GAAP financial measure.
Enstar Group Limited | Second Quarter 2022 | Form 10-Q                 15

Table of Contents
Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations
Six Months Ended June 30, 2021:
Our Annualized RLE % was positively impacted by a reduction of $58 million in the fair value of liabilities for which we have elected the fair value option in the 2017 and 2018 acquisition years as a result of increases in interest rates.
Additionally, annualized RLE % was positively impacted by favorable development in our professional indemnity/directors and officers line of business across our Lloyd’s portfolios and reductions in case reserve estimates for large claims on the 2012 and prior, 2016 and 2018 acquisition years and continued favorable actual versus expected loss experience in our workers’ compensation line of business on the 2017, 2020 and 2021 acquisition years.
Annualized Adjusted RLE %*, which excludes fair value adjustments, benefited from a $10 million favorable impact as a result of lower than expected asbestos related claim frequency related to our defendant A&E liabilities attributable to the 2019 acquisition year.
*Non-GAAP measure; refer to “Non-GAAP Financial Measures” section for reconciliation to the applicable GAAP financial measure.

Enstar Group Limited | Second Quarter 2022 | Form 10-Q                 16

Table of Contents
Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations
Investment Results
We strive to structure our investment holdings and the duration of our investments in a manner that recognizes our liquidity needs, including our obligation to pay losses and future policyholder benefit expenses.
The components of our investment results split between our fixed income assets (which includes our short-term and fixed maturity investments classified as trading and AFS, fixed maturity investments included within funds held-directly managed, cash and cash equivalents, including restricted cash and cash equivalents, and funds held by reinsured companies, collectively our “Fixed Income” assets) and other investments ("Other Investments") (which includes equities, the remainder of funds held-directly managed and equity method investments) are as follows:
Three Months Ended June 30,
20222021
Fixed IncomeOther InvestmentsTotalFixed IncomeOther InvestmentsTotal
(in millions of U.S. dollars)
Net investment income$84 $22 $106 $61 $15 $76 
Net realized (losses) gains (30)(8)(38)
Net unrealized (losses) gains(379)(212)(591)105 295 400 
Earnings (losses) from equity method investments— — (3)(3)
TIR ($)$(325)$(197)$(522)$171 $308 $479 
Annualized TIR %(9.1)%(14.0)%(10.5)%5.1 %21.5 %10.0 %
Annualized Adjusted TIR %*2.2 %(14.0)%(2.2)%1.9 %21.5 %7.8 %
Six Months Ended June 30,
20222021
Fixed IncomeOther InvestmentsTotalFixed IncomeOther InvestmentsTotal
(in millions of U.S. dollars)
Net investment income$145 $41 $186 $109 $29 $138 
Net realized (losses) gains (65)(10)(75)(7)(5)
Net unrealized (losses) gains(678)(294)(972)(89)479 390 
Earnings from equity method investments— 32 32 — 115 115 
TIR ($)$(598)$(231)$(829)$13 $625 $638 
Annualized TIR %(7.9)%(8.6)%(8.1)%0.2 %21.5 %6.8 %
Annualized Adjusted TIR %*1.9 %(8.6)%(0.8)%1.8 %21.5 %8.0 %
*Non-GAAP measure; refer to “Non-GAAP Financial Measures” section for reconciliation to the applicable GAAP financial measure.
Enstar Group Limited | Second Quarter 2022 | Form 10-Q                 17

Table of Contents
Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations
Net Investment Income
The below charts are in millions of U.S. dollars.
https://cdn.kscope.io/445635761414a66fdc86c42f353ffe52-esgr-20220630_g6.jpg https://cdn.kscope.io/445635761414a66fdc86c42f353ffe52-esgr-20220630_g7.jpg
Three and Six Months Ended June 30, 2022 versus 2021: Net investment income increased primarily due to:
an increase in our average aggregate fixed income assets of $2.1 billion and $3.3 billion, respectively, due to new business during the past year;
the reinvestment of fixed maturities at higher yields; and
the impact of rising interest rates on our investments that are subject to floating interest rates.
Our annualized book yield decreased by 33 and 21 basis points, respectively, as a result of timing differences, whereby we experienced a significant increase to our average aggregate fixed income assets as of June 30, 2022 by recording $1.9 billion in funds held by reinsured companies as a result of the Aspen transaction, with net investment income only being recognized for the period from the May 20, 2022 closing of the transaction to June 30, 2022.
Net Realized and Unrealized (Losses) Gains
The below charts are in millions of U.S. dollars.
https://cdn.kscope.io/445635761414a66fdc86c42f353ffe52-esgr-20220630_g8.jpghttps://cdn.kscope.io/445635761414a66fdc86c42f353ffe52-esgr-20220630_g9.jpg
Three and Six Months Ended June 30, 2022 versus 2021: Net realized and unrealized losses increased relative to the prior period net realized and unrealized gains primarily due to:
net realized and unrealized losses on fixed income securities of $409 million and $743 million for the three and six months ended June 30, 2022, respectively, compared to net gains of $110 million and net losses of $96 million for the three and six months ended June 30, 2021, respectively. The unfavorable movements of $519 million and $647 million, respectively, were primarily driven by rising interest rates across U.S., U.K. and European markets, in addition to widening credit spreads in the current period; and
net realized and unrealized losses on other investments, including equities, of $220 million and $304 million for the three and six months ended June 30, 2022, respectively, compared to net gains of $296 million and $481 million for the three and six months ended June 30, 2021, respectively. The unfavorable movements of $516 million and $785 million, respectively, were primarily driven by: