Philadelphia's management is godawful. They refuse to add a pick in order to ship out the Van Riemsdyk contract, just days after sending 3 picks to Carolina for defensive horror show/lousy human Tony DeAngelo. Two of those picks would have been enough to get rid of the JVR contract and give them enough money to sign Gaudreau.
Reportedly, Gaudreau contacted the Flyers as soon as free agency opened and said he wanted to play there even if it meant slightly less than he could get on the open market, and Philly essentially said no.
So, in a nutshell, Philly opted for this:
James Van Riemsdyk at $7 million
Tony DeAngelo at $5 million
trading 3 picks
Over this:
Johnny Gaudreau at $9 million
$3 million extra cap room
trading 2 picks
This is just insanity. Sheer insanity.