Sign and trades like you're suggesting here don't happen. EDM passes. I also think that contract is a tad rich for Debrusk. If I had to choose between him at 5 * 5 or Foegele at the 3.5 * 4 he's likely in the range of, I take the latter.

Why wouldn’t the oilers just sign him themselves?

the sign and trade is so the free market doesn't drive up his AAV more.

tbh I don't know anything about Merkulov other than that his numbers look good. but for the Sens to not take a 1st, he'd really need to be in the "can be a properly good top 9 NHL forward as early as next season" tier

Especially if they're a LH LW. On the left we've realistically got Tkachuk, Greig/Pinto, Joseph, and Kelly plus Jarventie and Crookshank ready to come up. If they were on RW it'd be different, but it just doesn't seem like enough of a need to pass on a 1st.

I’d rather keep Ullmark than trade him for marginal picks. His value has been shown. No reason to give him up for flyers. Not disrespecting 2nd and 3rd round picks, but I’d rather have the certainty of a good backup.

This last year, a 2nd and 3rd end up securing Tyler Toffoli. I believe that Ullmark is just as valuable (if not more) even if he’s just viewed as a one year rental for Boston. Maybe he signs long term taking more term for a discount. He seems to love it here.

Edmonton declines. They can keep their 2nd and make DeBrusk an offer themselves. If he wants to go home he'll take a discount too.

OTT declines, not trading chych within division. and that dont get chych not even close