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Stockholders' Equity - Additional Information (Detail) - USD ($)
1 Months Ended 12 Months Ended
Mar. 15, 2018
Feb. 29, 2020
Feb. 28, 2018
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Sep. 30, 2019
Jun. 30, 2018
Dec. 31, 2016
Nov. 30, 2015
Stockholders Equity Note [Line Items]                    
Remaining authorized repurchases under share repurchase program       $ 627,100,000            
Amount of equity unavailable for dividends or advances from subsidiaries       6,900,000,000            
Stockholders' equity attributable to Alleghany stockholders       8,776,734,000 $ 7,692,710,000 $ 8,514,063,000     $ 7,939,945,000  
Amount available for dividends or advances, parent level       $ 1,900,000,000            
Dividends paid $ 154,000,000.0       153,967,000          
Dividend Declared in 2018                    
Stockholders Equity Note [Line Items]                    
Special dividend declared per share     $ 10.00              
Dividend record date     Mar. 05, 2018              
Dividend payable nature       special            
Dividend Declared in 2020                    
Stockholders Equity Note [Line Items]                    
Dividend payable nature       special            
Dividend Declared in 2020 | Subsequent Event                    
Stockholders Equity Note [Line Items]                    
Special dividend declared per share   $ 15.00                
Dividend record date   Mar. 05, 2020                
Dividend payable date   Mar. 16, 2020                
Operating Segments                    
Stockholders Equity Note [Line Items]                    
Stockholders' equity attributable to Alleghany stockholders       $ 9,317,200,000            
Operating Segments | Reinsurance Segment and Insurance Segment                    
Stockholders Equity Note [Line Items]                    
Stockholders' equity attributable to Alleghany stockholders       8,416,300,000            
Statutory net income of insurance operating units       690,900,000 263,600,000          
Combined statutory capital and surplus of insurance operating unit       7,000,000,000.0 6,500,000,000          
Transatlantic Reinsurance Company                    
Stockholders Equity Note [Line Items]                    
Dividends paid       220,000,000.0 $ 280,000,000.0 $ 270,000,000.0        
Transatlantic Reinsurance Company | Maximum                    
Stockholders Equity Note [Line Items]                    
Amount of dividend that can be declared without regulatory approval       $ 41,500,000            
Stock Repurchase Programs 2015                    
Stockholders Equity Note [Line Items]                    
Aggregate amount of common stock authorized for repurchase                   $ 400,000,000.0
Stock Repurchase Programs 2018                    
Stockholders Equity Note [Line Items]                    
Aggregate amount of common stock authorized for repurchase               $ 400,000,000.0    
Stock Repurchase Programs 2019                    
Stockholders Equity Note [Line Items]                    
Aggregate amount of common stock authorized for repurchase             $ 500,000,000.0