The problem with this though is that the Pens aren't going to have those high of 1st round picks in the next 4 years because they still have Crosby, Geno, Guentzel, and now Marner. It just doesn't make sense for them to trade Marner to a contender, not to mention the cap struggle this would put the Pens in the next coming year with Simon, Kahun, Riikola, Murray, and Jarry all coming off contracts in which they would most likely get raises, Guentzel coming off LTIR, and the only person with a lot of cap expiring is Schultz.

Kessel was unsigned. Marner is signed for 6 seasons. Not similar.

Now when Brian "The Brain" Burke made the trade he assumed (for whatever reason) the Leafs picks wouldn't be nearly as high. He thought he could talk the Leafs to success since he is the smartest person in the world.
This is terrible trade for Marner as the three picks...will be about 26th overall.

and when Jake comes off LTIR then what?
Especially considering the cap hold over bonus.

Was Phil and RFA when they moved him?

Yes

But Kessel also signed at 9.5% of the cap as opposed to Marner's 13.4%. When signed, Kessel was 47th in the league in cap hit, Marner 7th. So the 6 years thing actually hurts Marner in the comparison.

We also need to keep in mind that Kessel had 2 30 goal seasons when he signed that 5x5.4 million dollar deal. Marner has no 30 goal seasons. No doubt should Marner should be worth less than what Kessel went for in 2010.

No.