So structuring the deal so that the signing bonus is only taxed at the low end (15%) as per the Article XVI of the US-Canada tax treaty? Great idea!

O wait.. signing bonuses aren't calculated into the buyout formula so you're essentially handcuffing a team AGAIN with a buyout proof contract if he doesnt perform like a certain big name star who, ironically, was "drawn in by the potential of playing with the best player in the world locked up long term".

Your solution is to have Lucic 2.0 (or mini-Lucic, Lucic Jr. ...whichever tickles your fancy)
And there it is.. the dumbest thing I've read all day.

We're done here, Chiarelli.

So Dubas shouldn't have signed Matthews to a bonus-laden contract because it turned out bad with Lucic? That's a silly argument. Each player contract should be judged on it's own merits.

When you talk about that tier of player ($3-5M range) the chances of them failing are bigger than what a top tier player would be. If McDavid was paid $12,499,999 signing bonus every July 1 and only gets paid $1 over the year it wouldnt be an issue because he's the top player in the league. IF he were to be injured and does NOT come back to form, best player or not that contract becomes a liability plain and simple.

You're stretching here, Chiarelli. If Matthews ends up being a 70pt player his entire career because of injuries (he's already shown he's a bit prone), then that would be one of the worst contracts in the league.
Right now looks good, the team has no safety net if things go south a la Lucic.

Lucic's 1st year was pretty great. Nobody complained about his $6M cap hit. Nobody talked about him taking a piss in years 2 and 3. Everybody though talked about years 5 - 7 and how that contract looks and everyone pretty much said Chiarelli messed up (more on term, than on AAV) since that contract is extremely tough to buy out.

All about balancing safety net between player and team. Zucarello is a prime example of a huge mistake in the next few years. Watch.

Say we did get Connelly, to compete with FLA offer, we wouldve had to pony up $4M AAV for 3 years and say a nice signing bonus as you suggested. Buyout proof contract all over again.
If he doesnt perform to that contract, the Oilers are now screwed out of 4M + 750 Lucic reten + 1.33M Pouliot buyout + 300k Gryba buyout + 2.5M Sekera buyout... missing out on a pretty good UFA market next year.

So you see handing out buyout proof contracts, big or small, just so you dont overpay as much to get players in Edmonton is exactly the move Holland SHOULDN'T make.