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SEGMENT REPORTING - Summary of Segment Information (Details)
$ in Thousands
 12 Months Ended
Dec. 31, 2020
USD ($)
employee
Dec. 31, 2019
USD ($)
employee
Dec. 31, 2018
USD ($)
employee
Segment Reporting Information [Line Items]      
Total revenues $ 16,207,106 $ 15,309,508 $ 16,631,172
Income (loss) from operations 673,268 789,976 912,083
Depreciation and amortization 101,727 100,449 96,729
Total assets $ 5,144,258 $ 4,641,060 $ 4,427,412
Average headcount (employee) | employee 15,119 15,551 15,204
NAST      
Segment Reporting Information [Line Items]      
Total revenues $ 11,312,553 $ 11,283,692 $ 12,346,757
Income (loss) from operations 508,475 722,763 821,844
Depreciation and amortization 25,314 24,508 25,290
Total assets $ 2,946,409 $ 2,550,010 $ 2,567,120
Average headcount (employee) | employee 6,811 7,354 7,387
Global Forwarding      
Segment Reporting Information [Line Items]      
Total revenues $ 3,100,525 $ 2,327,913 $ 2,487,744
Income (loss) from operations 175,513 80,527 91,626
Depreciation and amortization 34,550 36,720 35,148
Total assets $ 1,392,411 $ 1,021,592 $ 969,736
Average headcount (employee) | employee 4,708 4,766 4,711
All Other and Corporate      
Segment Reporting Information [Line Items]      
Total revenues $ 1,794,028 $ 1,697,903 $ 1,796,671
Income (loss) from operations (10,720) (13,314) (1,387)
Depreciation and amortization 41,863 39,221 36,291
Total assets $ 805,438 $ 1,069,458 $ 890,556
Average headcount (employee) | employee 3,600 3,431 3,106