I definitely hope we can re-sign him, he's sick. He's not Matthews/Marner level, but he's damn, damn good. He'd be a top 2 forward on the majority of teams, and the best forward on some teams. I'd be totally fine giving him $9 mil AAV, 8 years, but hopefully not too much more than that.
It's really too bad we went big money, long term and full NMCs with both JT and Rielly. They're good players too, but Matthews, Marner and Nylander are the trio we want to continue to build around - they're all better than JT/Rielly, and younger (Matthews 25, Marner 25, Willie 26, Rielly 28, JT 32). Like even if all we got was a modified NTC for the last year (or ideally last few years) of JT's deal, we'd be in a much better spot, would have the option to trade him, keep Matthews/Marner/Nylander, and still fill out a nice team around them.
On the bright side, JT's deal does expire just 1 year after Matthews and Nylander. So potentially 2024/25 would be a mega-cap-squeeze, where we'd have to gut the team a bit and have weak depth, but it would only last 1 year. Like even if Matthews/Marner/Nylander collectively get ~$4-5 mil in raises, that's way less than the $11 mil off the books with JT, and the cap is going up. IMO if we're thinking long term, we don't let any of Matthews/Marner/Nylander walk just to avoid slight overpayment, even if it means 2024/25 is rough.