The cap really limits the financial angle unless a trade was going to involve a buyout (which makes no sense). It's a bit silly to speculate without much of a timeline (though he did say the last year)
The most extreme example is probably Nick Schmaltz - his 7x5.85 deal only paid $3M in each of the first 2 years, so the remaining 5 (including this one) work out to a smidge under $35M in remaining cash.
If cash were much of an issue, we probably wouldn't have seen all of Coleman/Zadorov/Gudbranson/Pitlick (backloaded deal worth $2.2M vs. his 1.75 AAV this year). If he attempted Monny trade that cost real money after all of those then maybe that's where ownership draws the line, but I'm sure budget plans were in place well before then.
I suspect most owners would want to be consulted on any deal involving a $5M+ player with as many years w/ the franchise.
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