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REVENUE FROM CONTRACTS WITH CUSTOMERS - Total Revenues Disaggregated by Major Service Line and Timing of Recognition (Details) - USD ($)
$ in Thousands
 12 Months Ended
Dec. 31, 2020
Dec. 31, 2019
Dec. 31, 2018
Disaggregation of Revenue [Line Items]      
Total revenues $ 16,207,106 $ 15,309,508 $ 16,631,172
NAST      
Disaggregation of Revenue [Line Items]      
Total revenues 11,312,553 11,283,692 12,346,757
Global Forwarding      
Disaggregation of Revenue [Line Items]      
Total revenues 3,100,525 2,327,913 2,487,744
All Other and Corporate      
Disaggregation of Revenue [Line Items]      
Total revenues 1,794,028 1,697,903 1,796,671
Operating Segments | NAST      
Disaggregation of Revenue [Line Items]      
Total revenues 11,312,553 11,283,692 12,346,757
Operating Segments | Global Forwarding      
Disaggregation of Revenue [Line Items]      
Total revenues 3,100,525 2,327,913 2,487,744
Operating Segments | All Other and Corporate      
Disaggregation of Revenue [Line Items]      
Total revenues 1,794,028 1,697,903 1,796,671
Transportation      
Disaggregation of Revenue [Line Items]      
Total revenues 15,147,562 14,322,295 15,515,921
Transportation | Performance obligations completed over time      
Disaggregation of Revenue [Line Items]      
Total revenues 15,147,562 14,322,295 15,515,921
Transportation | Operating Segments | NAST | Performance obligations completed over time      
Disaggregation of Revenue [Line Items]      
Total revenues 11,312,553 11,283,692 12,346,757
Transportation | Operating Segments | Global Forwarding | Performance obligations completed over time      
Disaggregation of Revenue [Line Items]      
Total revenues 3,100,525 2,327,913 2,487,744
Transportation | Operating Segments | All Other and Corporate | Performance obligations completed over time      
Disaggregation of Revenue [Line Items]      
Total revenues 734,484 710,690 681,420
Sourcing      
Disaggregation of Revenue [Line Items]      
Total revenues 1,059,544 987,213 1,115,251
Sourcing | Performance obligations completed at a point in time      
Disaggregation of Revenue [Line Items]      
Total revenues 1,059,544 987,213 1,115,251
Sourcing | Operating Segments | NAST | Performance obligations completed at a point in time      
Disaggregation of Revenue [Line Items]      
Total revenues 0 0 0
Sourcing | Operating Segments | Global Forwarding | Performance obligations completed at a point in time      
Disaggregation of Revenue [Line Items]      
Total revenues 0 0 0
Sourcing | Operating Segments | All Other and Corporate | Performance obligations completed at a point in time      
Disaggregation of Revenue [Line Items]      
Total revenues $ 1,059,544 $ 987,213 $ 1,115,251