Tearsheet

Octave Specialty (OSG)


Market Price (1/19/2026): $6.08 | Market Cap: $292.5 Mil
Sector: Financials | Industry: Life & Health Insurance

Octave Specialty (OSG)


Market Price (1/19/2026): $6.08
Market Cap: $292.5 Mil
Sector: Financials
Industry: Life & Health Insurance

Investment Highlights Why It Matters Detailed financial logic regarding cash flow yields vs trend-riding momentum.


0 Cash is significant % of market cap
Net D/ENet Debt/Equity. Debt net of cash. Negative indicates net cash. Equity is taken as the Market Capitalization is -164%
Weak multi-year price returns
2Y Excs Rtn is -75%, 3Y Excs Rtn is -105%
Weak revenue growth
Rev Chg QQuarterly Revenue Change % is -4.9%
1 Strong revenue growth
Rev Chg LTMRevenue Change % Last Twelve Months (LTM) is 144%
  Not cash flow generative
CFO/Rev LTMCash Flow from Operations / Revenue (Sales), Last Twelve Months (LTM) is -51%, FCF/Rev LTMFree Cash Flow / Revenue (Sales), Last Twelve Months (LTM) is -51%
2 Low stock price volatility
Vol 12M is 36%
  Yield minus risk free rate is negative
ERPEquity Risk Premium (ERP) = Total Yield - Risk Free Rate, Reflects the premium above risk free assets offered by the investment. is -272%
3 Megatrend and thematic drivers
Megatrends include US Energy Independence. Themes include US Oilfield Technologies.
  Key risks
OSG key risks include [1] operational execution challenges in integrating its acquired businesses and [2] a weak financial position reflected in a low Altman Z-score and significant debt.
0 Cash is significant % of market cap
Net D/ENet Debt/Equity. Debt net of cash. Negative indicates net cash. Equity is taken as the Market Capitalization is -164%
1 Strong revenue growth
Rev Chg LTMRevenue Change % Last Twelve Months (LTM) is 144%
2 Low stock price volatility
Vol 12M is 36%
3 Megatrend and thematic drivers
Megatrends include US Energy Independence. Themes include US Oilfield Technologies.
4 Weak multi-year price returns
2Y Excs Rtn is -75%, 3Y Excs Rtn is -105%
5 Weak revenue growth
Rev Chg QQuarterly Revenue Change % is -4.9%
6 Not cash flow generative
CFO/Rev LTMCash Flow from Operations / Revenue (Sales), Last Twelve Months (LTM) is -51%, FCF/Rev LTMFree Cash Flow / Revenue (Sales), Last Twelve Months (LTM) is -51%
7 Yield minus risk free rate is negative
ERPEquity Risk Premium (ERP) = Total Yield - Risk Free Rate, Reflects the premium above risk free assets offered by the investment. is -272%
8 Key risks
OSG key risks include [1] operational execution challenges in integrating its acquired businesses and [2] a weak financial position reflected in a low Altman Z-score and significant debt.

Valuation, Metrics & Events

OSG Stock


Why The Stock Moved


Qualitative Assessment

AI Analysis | Feedback

Below are the key points for Octave Specialty (OSG) stock movement from October 31, 2025, to January 19, 2026:

1. Ambac Financial Group rebranded as Octave Specialty Group, Inc. and began trading under the new ticker symbol "OSG" on November 20, 2025. This strategic shift moved the company from a legacy financial guarantee business to a focused specialty insurance platform, aiming to build and acquire high-performing managing general agency (MGA) businesses.

2. Octave Specialty Group reported its Third Quarter 2025 financial results on November 11, 2025, showing better-than-expected earnings per share (EPS). Despite a net loss of $32 million and revenue missing forecasts, the EPS of -$0.06 significantly surpassed the anticipated -$0.23, leading to a nearly 5% rise in the company's stock price in after-hours trading.

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Stock Movement Drivers

Fundamental Drivers

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Market Drivers

10/31/2025 to 1/18/2026
ReturnCorrelation
OSG  
Market (SPY)1.4%6.3%
Sector (XLF)4.0%23.0%

Fundamental Drivers

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Market Drivers

7/31/2025 to 1/18/2026
ReturnCorrelation
OSG  
Market (SPY)9.7%6.3%
Sector (XLF)4.3%23.0%

Fundamental Drivers

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Market Drivers

1/31/2025 to 1/18/2026
ReturnCorrelation
OSG  
Market (SPY)15.9%6.3%
Sector (XLF)6.9%23.0%

Fundamental Drivers

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Market Drivers

1/31/2023 to 1/18/2026
ReturnCorrelation
OSG  
Market (SPY)76.5%6.3%
Sector (XLF)55.7%23.0%

Return vs. Risk


Price Returns Compared

 202120222023202420252026Total [1]
Returns
OSG Return-----10%-19%-27%
Peers Return36%8%12%34%-0%-2%116%
S&P 500 Return27%-19%24%23%16%1%85%

Monthly Win Rates [3]
OSG Win Rate----50%0% 
Peers Win Rate70%50%50%63%57%20% 
S&P 500 Win Rate75%42%67%75%67%100% 

Max Drawdowns [4]
OSG Max Drawdown-----10%-21% 
Peers Max Drawdown-7%-14%-12%-1%-14%-3% 
S&P 500 Max Drawdown-1%-25%-1%-2%-15%0% 


[1] Cumulative total returns since the beginning of 2021
[2] Peers: RYAN, BRO, AJG, WRB, MKL.
[3] Win Rate = % of calendar months in which monthly returns were positive
[4] Max drawdown represents maximum peak-to-trough decline within a year
[5] 2026 data is for the year up to 1/16/2026 (YTD)

How Low Can It Go

OSG has limited trading history. Below is the Financials sector ETF (XLF) in its place.

Unique KeyEventXLFS&P 500
2022 Inflation Shock2022 Inflation Shock  
2022 Inflation Shock% Loss% Loss-26.9%-25.4%
2022 Inflation Shock% Gain to Breakeven% Gain to Breakeven36.7%34.1%
2022 Inflation ShockTime to BreakevenTime to Breakeven525 days464 days
2020 Covid Pandemic2020 Covid Pandemic  
2020 Covid Pandemic% Loss% Loss-43.3%-33.9%
2020 Covid Pandemic% Gain to Breakeven% Gain to Breakeven76.5%51.3%
2020 Covid PandemicTime to BreakevenTime to Breakeven295 days148 days
2018 Correction2018 Correction  
2018 Correction% Loss% Loss-26.1%-19.8%
2018 Correction% Gain to Breakeven% Gain to Breakeven35.2%24.7%
2018 CorrectionTime to BreakevenTime to Breakeven338 days120 days
2008 Global Financial Crisis2008 Global Financial Crisis  
2008 Global Financial Crisis% Loss% Loss-83.7%-56.8%
2008 Global Financial Crisis% Gain to Breakeven% Gain to Breakeven515.2%131.3%
2008 Global Financial CrisisTime to BreakevenTime to Breakeven4,470 days1,480 days

Compare to RYAN, BRO, AJG, WRB, MKL

In The Past

SPDR Select Sector Fund's stock fell -26.9% during the 2022 Inflation Shock from a high on 1/12/2022. A -26.9% loss requires a 36.7% gain to breakeven.

Preserve Wealth

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Asset Allocation

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About Octave Specialty (OSG)

Overseas Shipholding Group, Inc., together with its subsidiaries, owns and operates a fleet of oceangoing vessels. Its vessels are engaged in the transportation of crude oil and petroleum products in the United States flag trade. As of December 31, 2021, the company owned or operated a fleet of 24 vessels totaling an aggregate of approximately 1.7 million deadweight tons. It serves independent oil traders, refinery operators, and the United States and international government entities. The company was founded in 1948 and is headquartered in Tampa, Florida.

AI Analysis | Feedback

Here are 1-3 brief analogies for Overseas Shipholding Group, Inc. (OSG), which is identified by the symbol OSG. (Please note that "Octave Specialty" does not appear to be the correct company name for the OSG symbol; OSG refers to Overseas Shipholding Group, Inc.):

  • A marine **Kinder Morgan**, for crude oil and refined products.
  • The **Maersk** of U.S. domestic oil tankers.
  • A floating **Union Pacific** for U.S. coastal oil transport.

AI Analysis | Feedback

  • Crude Oil and Petroleum Product Transportation: Overseas Shipholding Group (OSG) operates a fleet of tankers to transport crude oil and various refined petroleum products globally.
  • Specialty Jones Act Services: The company provides specialized maritime transportation services within the U.S. Jones Act trade, including shuttle tankers and vessels for niche liquid cargoes.

AI Analysis | Feedback

Octave Specialty (symbol: OSG) refers to Overseas Shipholding Group, Inc. (OSG), a public company specializing in crude oil and petroleum product transportation services, primarily in the U.S. flag market.

The company sells primarily to other companies (B2B). Its major customers are large integrated oil companies and refiners that require marine transportation services. Based on their public filings, key customer companies include:

  • BP Shipping Limited (part of BP plc, symbol: BP)
  • ExxonMobil Oil Corporation (part of Exxon Mobil Corporation, symbol: XOM)
  • Phillips 66 Company (part of Phillips 66, symbol: PSX)
  • Valero Marketing and Supply Company (part of Valero Energy Corporation, symbol: VLO)

Overseas Shipholding Group's 2023 10-K filing indicates significant customer concentration, with two customers each accounting for 20% or more of their voyage and charter revenues during that year.

AI Analysis | Feedback

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AI Analysis | Feedback

Claude LeBlanc President and Chief Executive Officer

Mr. LeBlanc has served as President and Chief Executive Officer of Octave Specialty Group, Inc. (formerly Ambac Financial Group, Inc.) since January 1, 2017. He is an accomplished financial executive with nearly three decades of experience in the financial services sector, encompassing strategic management, corporate development, and financial restructuring. Prior to his current role, he was the Chief Financial Officer and Chief Restructuring Officer at Syncora Holdings Ltd. from January 2010 to December 2016, and served as Executive Vice President and Special Advisor to the Board at Syncora from 2006 to 2009. His career also includes serving as Senior Vice President of Corporate Development & Strategy at XL Capital from 2001 to 2006, and Chief Operating Officer and Head of Corporate Development at TransWorld International (London Telecom) from 1999 to 2001. He began his career at PwC, where he was a Principal and Vice President from 1991 to 1999. Mr. LeBlanc oversaw the successful sale of the company's legacy financial guarantee business, marking a significant step in the company's transformation.

David Trick Director of Finance/CFO

Mr. Trick has served as the Director of Finance/CFO of Octave Specialty Group, Inc. (formerly Ambac Financial Group, Inc.) since January 7, 2010. Further background details regarding his previous companies managed, sales of companies, or a pattern of managing companies backed by private equity firms are not available in the provided information.

Dan McGinnis Chief Operating Officer

Mr. McGinnis has served as the Chief Operating Officer of Octave Specialty Group, Inc. (formerly Ambac Financial Group, Inc.) since November 30, 2021. Further background details regarding his previous companies managed, sales of companies, or a pattern of managing companies backed by private equity firms are not available in the provided information.

Karen Beyer Managing Director, Head of Investor Relations

Ms. Beyer was appointed as Managing Director, Head of Investor Relations for Octave Specialty Group, Inc. (formerly Ambac Financial Group, Inc.) on November 10, 2025. Further background details regarding her previous companies managed, sales of companies, or a pattern of managing companies backed by private equity firms are not available in the provided information.

AI Analysis | Feedback

The key risks for Octave Specialty (symbol: OSG) include challenges related to the integration of acquired businesses, the impact of legacy exposures and market trends on revenue growth, and broader financial challenges.

  1. Integration Risks from Acquisitions: Octave Specialty operates as a global specialty insurance firm that builds, buys, and scales niche insurance distribution and underwriting businesses. Bearish analysts express caution regarding the sustainability of the company's performance, specifically citing that the integration of newly acquired businesses presents operational and financial execution risks. These risks could potentially pressure margins or delay the realization of anticipated synergies. A recent acquisition of a smaller competitor, involving a $50 million investment, highlights these inherent integration challenges.
  2. Legacy Exposures and Market Trends: The company faces risks stemming from its legacy exposures and prevailing market trends, which could undermine sustainable revenue growth despite efforts in diversification and technology investments. Macroeconomic volatility and broader industry disruptions further threaten Octave Specialty's profit stability, leading to unpredictable earnings even with improvements in margins and scaling initiatives.
  3. Financial Challenges: Octave Specialty faces financial challenges, reflected in a "WEAK" overall financial health rating and an Altman Z-Score of 0.91. The company's financial stability is susceptible to factors like interest rate fluctuations; with a total debt of $200 million and a current interest rate of 5%, any increase in interest rates could significantly elevate financing costs.

AI Analysis | Feedback

The global energy transition and decarbonization efforts pose a clear emerging threat. A significant and accelerating shift towards renewable energy sources, electric vehicles, and other non-fossil fuel technologies, coupled with increasing environmental regulations and targets from international bodies like the IMO, threatens the long-term demand for crude oil and petroleum products. As the core business of OSG (Overseas Shipholding Group, Inc.) is the ocean transportation of these fossil fuels, a sustained decline in demand for these commodities could fundamentally erode its market, necessitating costly fleet modernization towards alternative fuels or cargo types.

AI Analysis | Feedback

Octave Specialty Group Inc. (OSG), formerly known as Ambac Financial Group, Inc., is a global specialty insurance firm. The company's primary business involves building, acquiring, and scaling niche insurance distribution and underwriting businesses. Its operations are focused on the U.S., U.K., and Bermuda markets.

Currently, the specific addressable market size for Octave Specialty Group's niche insurance products and services cannot be identified as a single, consolidated figure from publicly available information. While the company operates within the broader specialty insurance sector, detailed market sizing for their specific "niche" businesses across their targeted regions (U.S., U.K., and Bermuda) is not readily available. Therefore, the addressable markets for their main products or services cannot be precisely sized at this time.

AI Analysis | Feedback

Here are 3-5 expected drivers of future revenue growth for Octave Specialty (OSG) over the next 2-3 years:

  1. Acquisition and Expansion of Managing General Agencies (MGAs): Octave Specialty Group's core strategy post-rebranding is to build and acquire high-performing managing general agency (MGA) businesses across the US, UK, and Bermuda. This focused acquisition strategy is expected to be a primary driver of revenue growth as the company integrates new businesses into its portfolio.
  2. Organic Growth within the Insurance Distribution Segment: The company's Insurance Distribution segment has already demonstrated significant organic revenue growth, with a 40% increase in Q3 2025. This indicates a strong performance and expansion within its existing insurance distribution operations.
  3. Geographic Market Expansion: Octave Specialty Group's stated focus on acquiring MGA businesses "across the US, UK, and Bermuda" signals a clear intent for geographical expansion. This broader market reach is anticipated to contribute to increased revenue.
  4. Diversification into Specialty Insurance and Tech-Driven Operations: Octave's strategy involves diversification into specialty insurance and leveraging technology in its operations. This approach is aimed at improving revenue stability and operational efficiency, which can lead to enhanced market competitiveness and, consequently, revenue growth through more attractive and efficient product offerings.

AI Analysis | Feedback

Share Repurchases

  • Octave Specialty Group completed the repurchase of 3,100,000 shares, equivalent to 6.5% of the weighted average shares outstanding, as part of its capital management strategy.
  • Under an equity buyback plan announced on November 12, 2024, the company completed the repurchase of 1,229,332 shares for $15.11 million.
  • A buyback announced on March 30, 2022, resulted in the repurchase of 1,945,329 shares for $18.91 million.

Share Issuance

  • Shareholders of Octave Specialty Group have not been meaningfully diluted in the past year.

Outbound Investments

  • Octave Specialty Group successfully sold its legacy financial guarantee business for $420 million, enabling a strategic focus on its core specialty insurance operations.
  • The company has launched new professional lines Managing General Agents (MGAs) and converted an investment in a recently launched MGA to a majority stake.
  • Octave Specialty Group plans disciplined capital allocation to support startups and technology investments for future growth.

Capital Expenditures

  • The company plans disciplined capital allocation to support technology investments, aiming for robust performance in 2026 and beyond.
  • Octave Specialty Group has generated cashflows in excess of scheduled debt service and planned capital expenditures, allowing for returns to stockholders.

Trade Ideas

Select ideas related to OSG. For more, see Trefis Trade Ideas.

Unique Key

Recent Active Movers

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Peer Comparisons for Octave Specialty

Peers to compare with:

Financials

OSGRYANBROAJGWRBMKLMedian
NameOctave S.Ryan Spe.Brown & .Arthur J.WR Berkl.Markel  
Mkt Price6.0651.4880.01258.5267.882,059.5173.94
Mkt Cap0.36.626.566.327.025.926.2
Rev LTM2502,9635,34413,03014,64516,1469,187
Op Inc LTM--1,4712,682--2,076
FCF LTM-1275721,2991,7673,3302,3751,533
FCF 3Y Avg-14761,0841,9723,2542,5351,528
CFO LTM-1276401,3671,9163,3982,5931,642
CFO 3Y Avg-15191,1572,1333,3302,7701,645

Growth & Margins

OSGRYANBROAJGWRBMKLMedian
NameOctave S.Ryan Spe.Brown & .Arthur J.WR Berkl.Markel  
Rev Chg LTM143.9%24.3%17.4%15.6%11.3%-6.6%16.5%
Rev Chg 3Y Avg253.2%21.1%16.3%15.3%10.6%13.2%15.8%
Rev Chg Q-4.9%24.8%34.2%19.9%12.0%-2.5%15.9%
QoQ Delta Rev Chg LTM-1.3%5.3%8.0%4.5%2.8%-0.7%3.7%
Op Mgn LTM--27.5%20.6%--24.1%
Op Mgn 3Y Avg--28.0%19.5%--23.7%
QoQ Delta Op Mgn LTM---1.2%-0.5%---0.9%
CFO/Rev LTM-51.0%21.6%25.6%14.7%23.2%16.1%18.8%
CFO/Rev 3Y Avg309.5%21.3%24.8%19.1%25.2%17.1%23.0%
FCF/Rev LTM-51.0%19.3%24.3%13.6%22.7%14.7%17.0%
FCF/Rev 3Y Avg309.5%19.6%23.2%17.7%24.7%15.7%21.4%

Valuation

OSGRYANBROAJGWRBMKLMedian
NameOctave S.Ryan Spe.Brown & .Arthur J.WR Berkl.Markel  
Mkt Cap0.36.626.566.327.025.926.2
P/S1.22.25.05.11.81.62.0
P/EBIT-4.312.316.825.510.58.811.4
P/E-0.495.226.541.414.112.420.3
P/CFO-2.310.319.434.67.910.010.1
Total Yield-267.6%2.0%4.5%2.9%9.0%8.0%3.7%
Dividend Yield0.0%0.9%0.7%0.4%1.9%0.0%0.6%
FCF Yield 3Y Avg-7.5%4.4%3.4%14.1%11.4%7.5%
D/E0.00.50.30.20.10.20.2
Net D/E-1.60.50.30.2-0.9-0.3-0.0

Returns

OSGRYANBROAJGWRBMKLMedian
NameOctave S.Ryan Spe.Brown & .Arthur J.WR Berkl.Markel  
1M Rtn-26.9%-2.6%-0.2%2.0%-2.1%-4.9%-2.4%
3M Rtn-30.3%-2.4%-8.8%-7.6%-6.9%8.9%-7.2%
6M Rtn-30.3%-21.7%-22.7%-17.0%0.4%1.4%-19.4%
12M Rtn-30.3%-22.1%-23.7%-11.5%17.1%16.1%-16.8%
3Y Rtn-30.3%25.4%35.4%39.3%57.8%50.1%37.3%
1M Excs Rtn-29.6%-4.9%-3.2%0.5%-3.0%-5.8%-4.1%
3M Excs Rtn-35.0%-5.9%-13.0%-12.2%-11.1%4.8%-11.6%
6M Excs Rtn-40.5%-31.9%-32.9%-27.3%-9.8%-8.9%-29.6%
12M Excs Rtn-46.9%-38.4%-39.0%-26.8%-0.4%1.3%-32.6%
3Y Excs Rtn-105.1%-53.2%-42.6%-39.0%-22.9%-26.6%-40.8%

Financials

Segment Financials

Revenue by Segment
$ Mil20242023202220212020
Specialty Property & Casualty Insurance64182  
Insurance Distribution523126  
Corporate & Other945  
Legacy Financial Guarantee Insurance 451250  
Financial Guarantee   156496
Total125504283156496


Net Income by Segment
$ Mil20242023202220212020
Insurance Distribution65   
Specialty Property & Casualty Insurance0-6   
Corporate & Other-31-13   
Legacy Financial Guarantee Insurance 537   
Total-25523   


Assets by Segment
$ Mil20242023202220212020
Discontinued operations7,516    
Specialty Property & Casualty Insurance523316156  
Corporate & Other234226182  
Insurance Distribution15513893  
Legacy Financial Guarantee Insurance 7,29211,871  
Total8,4287,97212,302  


Short Interest

Short Interest: As Of Date12312025
Short Interest: Shares Quantity2,091,067
Short Interest: % Change Since 12152025-7.6%
Average Daily Volume651,130
Days-to-Cover Short Interest3.21
Basic Shares Quantity48,106,069
Short % of Basic Shares4.3%

SEC Filings

Expand for More
Report DateFiling DateFiling
09/30/202511/10/202510-Q (09/30/2025)
06/30/202508/07/202510-Q (06/30/2025)
03/31/202505/12/202510-Q (03/31/2025)
12/31/202403/06/202510-K (12/31/2024)
09/30/202411/12/202410-Q (09/30/2024)
06/30/202408/05/202410-Q (06/30/2024)
03/31/202405/06/202410-Q (03/31/2024)
12/31/202302/27/202410-K (12/31/2023)
09/30/202311/07/202310-Q (09/30/2023)
06/30/202308/07/202310-Q (06/30/2023)
03/31/202305/09/202310-Q (03/31/2023)
12/31/202203/01/202310-K (12/31/2022)
09/30/202211/08/202210-Q (09/30/2022)
06/30/202208/08/202210-Q (06/30/2022)
03/31/202205/10/202210-Q (03/31/2022)
12/31/202102/24/202210-K (12/31/2021)