Skyward Specialty [SKWD] vs Old Republic [ORI] Detailed Stock Comparison

TLDR: Quick Comparison Summary

Based on 20 vital metrics comparison: Skyward Specialty Insurance Group, Inc. wins in 12 metrics, Old Republic International Corp. wins in 7 metrics, with 0 ties. Skyward Specialty Insurance Group, Inc. appears stronger overall.

View Metrics Details

Vital Metrics Comparison

Metric Skyward Specialty Insurance Group, Inc. Old Republic International Corp. Better
P/E Ratio (TTM) 11.36 11.51 Skyward Specialty Insurance Group, Inc.
Price-to-Book Ratio 1.86 1.76 Old Republic International Corp.
Debt-to-Equity Ratio 11.88 30.07 Skyward Specialty Insurance Group, Inc.
PEG Ratio 0.06 0.12 Skyward Specialty Insurance Group, Inc.
EV/EBITDA 7.21 8.01 Skyward Specialty Insurance Group, Inc.
Profit Margin (TTM) 12.00% 10.24% Skyward Specialty Insurance Group, Inc.
Operating Margin (TTM) 17.60% 11.74% Skyward Specialty Insurance Group, Inc.
EBITDA Margin (TTM) 17.60% 11.74% Skyward Specialty Insurance Group, Inc.
Return on Equity 18.86% 16.31% Skyward Specialty Insurance Group, Inc.
Return on Assets (TTM) 3.50% 2.72% Skyward Specialty Insurance Group, Inc.
Free Cash Flow (TTM) $400.62M $1.16B Old Republic International Corp.
Dividend Yield N/A 9.08% N/A
1-Year Return -30.36% -1.51% Old Republic International Corp.
Price-to-Sales Ratio (TTM) 1.45 1.15 Old Republic International Corp.
Enterprise Value $1.74B $10.33B Old Republic International Corp.
EV/Revenue Ratio 1.23 1.13 Old Republic International Corp.
Revenue per Share (TTM) $35 $37 Old Republic International Corp.
Earnings per Share (Diluted) $4.07 $3.72 Skyward Specialty Insurance Group, Inc.
Beta (Stock Volatility) 0.60 0.77 Skyward Specialty Insurance Group, Inc.
Short % of Float 3.44% 4.45% Skyward Specialty Insurance Group, Inc.

Skyward Specialty Insurance Group, Inc. vs Old Republic International Corp. Stock Performance Analysis

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Performance Comparison

Short-term Returns

Stock1D1W1M3M6MYTD
Skyward Specialty Insurance Group, Inc.-3.11%-6.68%-2.09%-11.39%-5.42%-12.11%
Old Republic International Corp.-0.24%-3.47%-3.77%-12.58%-16.10%-14.40%

Long-term Returns

Stock1Y3Y5Y10Y15Y20Y
Skyward Specialty Insurance Group, Inc.-30.36%84.76%-14.50%-14.50%-14.50%-14.50%
Old Republic International Corp.-1.51%50.79%41.72%96.78%210.51%74.54%

Performance & Financial Health Analysis: Skyward Specialty Insurance Group, Inc. vs Old Republic International Corp.

MetricSKWDORI
Market Information
Market Cap i$2.06B$9.80B
Market Cap CategoryMid capMid cap
10 Day Avg. Volume i429,3591,200,119
90 Day Avg. Volume i428,6331,679,160
Last Close$42.73$37.04
52 Week Range$40.60 - $65.01$35.60 - $46.76
% from 52W High-34.27%-20.79%
All-Time High$65.05 (Jun 02, 2025)$46.76 (Dec 26, 2025)
% from All-Time High-34.31%-20.79%
Growth Metrics
Quarterly Revenue Growth0.27%0.19%
Quarterly Earnings Growth2.00%0.96%
Financial Health
Profit Margin (TTM) i0.12%0.10%
Operating Margin (TTM) i0.18%0.12%
Return on Equity (TTM) i0.19%0.16%
Debt to Equity (MRQ) i11.8830.07
Cash & Liquidity
Book Value per Share (MRQ)$24.92$24.28
Cash per Share (MRQ)$9.73$7.72
Operating Cash Flow (TTM) i$408.08M$1.16B
Levered Free Cash Flow (TTM) i$-67,062,124$-9,261,325,312
Dividends
Last 12-Month Dividend Yield iN/A9.08%
Last 12-Month Dividend i$0.00$3.69

Valuation & Enterprise Metrics Analysis: Skyward Specialty Insurance Group, Inc. vs Old Republic International Corp.

MetricSKWD (Apr 22, 2026)ORI (Apr 24, 2026)
Price Ratios
P/E Ratio (TTM) i11.3611.51
Forward P/E i8.4712.41
PEG Ratio i0.060.12
Price to Sales (TTM) i1.451.15
Price to Book (MRQ) i1.861.76
Market Capitalization
Market Capitalization i$2.06B$9.80B
Enterprise Value i$1.74B$10.33B
Enterprise Value Metrics
Enterprise to Revenue i1.231.13
Enterprise to EBITDA i7.218.01
Risk & Other Metrics
Beta i0.600.77
Book Value per Share (MRQ) i$24.92$24.28

Financial Statements Comparison: Skyward Specialty Insurance Group, Inc. vs Old Republic International Corp.

Financial Metrics

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Revenue

Operating Margin

Profit Margin

Long Term Debt

Income Flow Analysis

Financial Statements Comparison

Income Statement

MetricSKWD (2025)ORI (2025)
Revenue/Sales i1.42B9.14B
Cost of Goods Sold iN/AN/A
COGS % of Revenue i0.0%0.0%
Gross Profit iN/AN/A
Gross Margin i0.0%0.0%
Research & Development iN/AN/A
Operating Income (EBIT) iN/AN/A
Operating Margin i0.0%0.0%
EBITDA iN/AN/A
EBITDA Margin i0.0%0.0%
Pre-Tax Income i216.42M1.18B
Pre-Tax Income % of Revenue i15.2%13.0%
Income Tax i46.40M242.10M
Income Tax % of Revenue i3.3%2.6%
Net Income (Profit) i170.03M941.90M
Profit Margin i12.0%10.3%

Balance Sheet & Liquidity Metrics

MetricSKWD (2025)ORI (2025)
Cash & Equivalents i168.54M263.20M
Total Current Assets iN/AN/A
Total Current Assets % of Revenue i0.0%0.0%
Total Current Liabilities iN/AN/A
Total Current Liabilities % of Revenue i0.0%0.0%
Long-Term Debt i119.98M1.59B
Long-Term Debt % of Revenue i8.5%17.4%
Total Shareholders Equity i1.01B5.93B
Retained Earnings i267.15M5.52B
Retained Earnings % of Revenue i18.8%60.4%
Property, Plant & Equipment iN/AN/A

Cash Flow Statement Comparison

MetricSKWD (2025)ORI (2025)
Operating Cash Flow i-226.34M737.60M
Operating Cash Flow % of Revenue i-15.9%8.1%
Capital Expenditures i-5.45MN/A
Free Cash Flow i400.62M1.16B
FCF Margin i28.2%12.7%
Debt Repayment i-43.00M0
Common Stock Repurchase iN/A-123.80M

Short Interest & Institutional Ownership Analysis

MetricSKWDORI
Shares Short i1.40M8.02M
Short Ratio i2.784.02
Short % of Float i3.44%4.45%
Shares Outstanding i40.51M246.36M
Float Shares i40.69M241.89M
% Held by Insiders i8.09%7.65%
% Held by Institutions i87.90%79.72%
% Held by Public i4.01%12.63%

Dividend Analysis & Yield Comparison: Skyward Specialty Insurance Group, Inc. vs Old Republic International Corp.

MetricSKWDORI
Last 12-Month Dividend i$0.00$3.69
Last 12-Month Dividend Yield iN/A9.08%
3-Year Avg Annual Dividend i$0.00$2.59
3-Year Avg Dividend Yield iN/A1.54%
3-Year Total Dividends i$0.00$7.78
Ex-Dividend DateN/AMar 09, 2026