You're not getting Cirelli for any pick. You're going to get him by being able to take back a big contract. Far more likely that TB is able to move one or more of those contracts to teams said players are willing to waive for though - making room to resign Cirelli/Serg in the process. TB will try everything they can & trading one of these RFAs will be a last resort. To the point where the pick they get is close to meaningless.
We got ROR for a late 1st. We got Skinner for a 2nd. These type of deal never require an early pick.
In reality - you are honestly not getting a much different player by trading away 8 than you are by trading away 20. You need to curb your expectations I think... Otherwise you are going to end up disappointed. Nobody is trading away a superstar for 8ov any more than they would for 20ov.
My scenario is realistic while yours seems wildly optimistic.
Reinhart is essentially a complimentary player who most of us want to keep around - so don't take anything away from Rakell here. He'd be a very welcome addition.
We can use 8ov & HOPE to get a game breaking talent in 3 years if we are lucky. Or we could end up with Nylander/Mitts 3.0. Right now I'm all in on moving that pick to get to the damn playoffs.
See bolded-
1) If they are moving Cirelli it's because they couldn't move a big contract (most likely because the players won't waive their NMC). However if we had to take a player like Johnson, Gourde, or Killorn we could swing that. Ultimately we have no idea what TB would be looking for if they get to the point where moving Cirelli becomes something they have to consider. You and I could both speculate, but neither one of us has any real insight on the matter. We both agree moving Cirelli or Sergachev is likely a last resort. I'm certainly not putting all my eggs in that basket.
2) Those are 2 trades and both players forced their way out (to varying degrees) Skinner was a winger on an expiring deal anyhow. There was a lot more to the ROR deal than a late 1st round pick (it was actually the 1st pick of the 2nd round, but close enough) Zadorov was a mid 1st, Compher was a good prospect, even Grigs was a high pick although he was trending towards busting. For every deal you point out like that, there's a Jordan Staal or a Derek Stepan to counter your argument deals that required that high pick. Typically good young centers don't come cheap and that's our biggest need this offseason. Don't piss away our best asset to get one with.
3) Dead wrong. Late 1sts are largely used for rental players, early 1sts can yield good young players with term or high end prospects with years and years of team control. The difference in value is immense.
4) My scenario is, you only move the 8th overall pick for a good, young, 2C, otherwise you keep the pick. Not unrealistic at all.
Ultimately I don't want our GM to be afraid to use an 8th overall pick because his predecessors made poor picks. Do your HW and make the right pick. Don't get cute and pass on a player like Sergachev. Even worse than that, don't trade a pick like that for cap relief and depth players. That's a real good way to stay mired in mediocrity.