Threads like this are too much fun to pass up. However, I do like my hypothetical trades to operate within a hypothetical universe somewhat close to our own. My armchair GM-ing below is meant to stay within Euge's internal cap, while making moves that I legitimately feel could possibly happen. The latter is of course somewhat subjective...
1. OTT/PHI: Michalek for Simmonds
I'd float this to Holmgren and see if he bites. He's pressed for cap space, and Milo's expiring contract would give him that. If Milan winds up contributing, it probably wouldn't be hard to sign him to a more agreeable deal.
In return, the Sens pick up young forward with grit and heart. Mac could deploy him in a variety of lines and situations.
This move would also lessen the Sens payroll by ~$358,333 this season. They'd only wind up paying more than they were for Michalek in years 5-6 of Simmonds' contract. I think Euge would be up for that.
2. OTT/NYR: Conacher, pick package for Del Zotto
If the rumors of Del Zotto being on the block are true, I think rolling the dice on him is a better option than most other D-men available. It's a contract year for him, so if he doesn't pan out then it's a short marriage and you have some cash for free agency (unlike Cowen). The upside would be nice though, should he pan out and Murray re-signs him. He's young, so hopefully he'd make packaging a pick worth it.
As for Conacher, I'm not sold on him at all. I'd flip him like we did with Bishop and throw him into any trade that he could help with. I'd listen to the Rangers if they wanted a different prospect, though.
3. Keep Anderson OFF the block
Until the Sens stop giving up 50+ shots regularly, they're going to need 2 outstanding netminders sharing the load. Otherwise, it'll be a goalie burnout. If injury strikes Lehner after dealing Andy then you're truly screwed. Until the Sens have a legit #2 waiting in the wings, hold on to #41.
4. Start kicking tires on Spezza
If I make this move, I don't do it until the deadline. He'd be much more valuable to a contender, and by then you'll have more clubs throwing in the towel and willing to deal. But for now, I'd start placing calls and letting people know that Spez
might be available for a certain price. Plant the seed.
5. Sit tight and work with the kids
Let the B-Sens carousel continue, seeing if kids like Stone, JGP, and Puempel can stick during a lighter November schedule. Don't forget new kids like Ceci and Lazar could be ready for some big boy minutes in a season or two.
With that said, here's what my fictional Sens look like:
MacArthur - Turris - Ryan
ZBad - Spezza - Simmonds
Greening - Smith - Grant
Neil - JGP - Condra
Karlsson - Methot
Del Zotto - Borocop
Phillips - Gryba/Corvo
Andy - Lehner
So... how ****ing crazy am I?