While the Penguins have made some monumentally huge trades with rivals, one thing that might stand out is that those trades are pretty aged. In the modern day and age, teams are not willing or excited to work with their rivals. This was most on display at the deadline in 2017. The Pens were buyers, loading up on depth defensemen. The Flyers were selling and Mark Streit was an impending free agent.
Pens’ GM Jim Rutherford had talks with Flyers then-GM Ron Hextall but “the price was too high”. The price wasn’t very high for Tampa, who got Streit in exchange for expensive veteran Valtteri Filppula and a fourth round pick.