For a laugh I decided to sort Benning's trades by the type of stupidity involved in each one. I ended up with 9 different categories; suggestions welcome. Some trades are stupid in multiple ways. 2nd for Vey is the only one in four categories, so I guess that's my vote for worst.
Futures dealt for castoff prospect where Benning thinks he knows better:
Forsling for Clendenning
2nd for Vey
2nd for Baertschi
Shinkaruk for Granlund
5th for Larsen
Mallet, 3rd for Pedan
Horrifying contract:
Dorsett 4-year $10.6 million contract
Miller 3-year $18 million contract
Sutter 5-year $21.875 million contract
Sbisa 3-year $10.8 million contract
Bleeding draft picks:
Kassian, 5th for Prust
McCann, 2nd, 4th for Gudbranson, 5th
2nd, Bonino, Clenndening for Sutter, 3rd
3rd for Dorsett
2nd for Vey
2nd for Baertschi
Mallet, 3rd for Pedan
Unsatisfying return on a veteran:
Kesler for Bonino, Sbisa, 23rd pick
Garrison, Costello and a 7th for a 2nd
Lack for 3rd, 7th
Moves zero roster players at 2016 trade deadline
Overpayment for a player they targeted:
2nd, Bonino, Clenndening for Sutter, 3rd
3rd for Dorsett
2nd for Vey
2nd for Baertschi
Thinks a terrible roster player on another team is good:
Kesler for Bonino, Sbisa, 23rd pick
3rd for Dorsett
Kassian, 5th for Prust
Bartkowski 1-year $1.75 million contract
Overrates a "meat and potatoes" bottom-half-of-roster player:
McCann, 2nd, 4th for Gudbranson, 5th
2nd, Bonino, Clenndening for Sutter, 3rd
Fetish for players that management/coaches already knew:
2nd for Vey
2nd for Baertschi
Shinkaruk for Granlund
Miller 3-year $18 million contract
3rd for Dorsett
Bartkowski 1-year $1.75 million contract
Total failure to execute:
Moves zero roster players at 2016 trade deadline
Reasonable or irrelevant moves:
Bieksa for 2nd
McNally for 5th
Jensen and 6th for Etem
Fox for futures
Jeffrey for Conacher
Acton for Lain