There would have to be some kind of side agreement that Keith comes back for free (or something) if he decides things aren't working out. Keith's cap recapture is pretty crazy. The buyout calculator doesn't factor that in.

***EDIT*** I really do think you're on to something with Pius Suter too. I'm going to make sure you get all the credit for bringing this to capfriendly.

I don't think he'd retire before his contract is up; FLA is a team that's supposed to be on the upswing, and coupling that with Quenneville as the coach, I don't think Keith would bail.

I HOPE you're right. and I think you probably are. It's just a non.....zero% area of concern. So, how can you protect yourself from it.

True, crazier things can and have happened (Luongo issue).

I calculated the recapture penalties that CHI would face if Keith retired:

1.) If he retired the minute he got traded to FLA (20-21 season): ‭$3,455,129 AAV for three years
2.) If he retired after his first year in FLA (21-22 season): $‭5,182,694 AAV for two years
3.) If he retired in the last year of his contract (22-23 season): $‭‭10,365,387‬ AAV for one year

Isn't that crazy?!?! anything $3M+ for 1 player that's still 24m ATOI???

Yup. I agree with your first notion though, that FLA/Keith would verbally agree to go on LTIR. Luongo retired because he wanted to stay in FLA post-career and have a higher-level job within the Panther's organization; Keith would likely return to CHI post-career and wouldn't mind technically staying on LTIR.

Your math is wrong for 2 and 3. CHI is on the hook for roughly $10m recapture if Keith is traded this summer. That number won't change.
1) is correct
2) would be $5m
3) would be $10m

Edit* even with $1m/yr retained it wouldn't change those number much.

So it's a static cap benefit amount, regardless of the date of retirement. Woof.

I re-did the numbers in the original post so others don't get confused.

Correct. NSH is still on the hook for $24m if Weber retires before his contract expires for instance. So if he retired with 2 years left NSH gets hit with a $12m x 2 penalty, he retires with 1 year left they would get hit with all $24m in one season.