A year, sure.  I am also OK with going year to year on a guy like this, especially when we have no idea what contracts will look like in 2022.

29 minutes ago, Squirmin' for Yermin said:

why?  He will have played the entire year with us.  I believe we can (if that's still a thing in 2021)

He already was QO'd in the past and a player can only be hit with this tag once.

Hahn is typically good at extensions, but for rookies or pre-arb players. Lynn has already made his money so I see less incentive for him to accept an extension. Perhaps he would accept a discounted extension at 2/$30M to hedge against the performance risk due to age or switching to a different organization, but I really don't see a lot of incentive for him otherwise, especially accepting  a discounted extension.

17 minutes ago, EloyJenkins said:

LOVE the idea of rework his deal for this year. 3/45-50 is perfect. Also still allows for another starter signing and gives you a strong 3 year window with everyone on board, while still allowing the future to get it figured out (Crochet, Dalquist, Kelley). 

Exactly

2 minutes ago, thxfrthmmrs said:

Hahn is typically good at extensions, but for rookies or pre-arb players. Lynn has already made his money so I see less incentive for him to accept an extension. Perhaps he would accept a discounted extension at 2/$30M to hedge against the performance risk due to age or switching to a different organization, but I really don't see a lot of incentive for him otherwise, especially accepting  a discounted extension.

I’d be all over 2/$30M. I’d even do 2/$40M tbh. Keep the top 3 together thru 2023.

Lock him up! Lock him up!

6 minutes ago, JUSTgottaBELIEVE said:

I’d be all over 2/$30M. I’d even do 2/$40M tbh. Keep the top 3 together thru 2023.

I'll be more hesitant if it's 2/$40M deal, mainly because I don't see him getting much more than that at his age, unless he improves even more. Also, you're removing flexibility to reassess next offseason and spending on other pitchers or areas of need, and taking on the performance and injury risk with little incentive. I'll definitely extend him at a discount, not when it's at or near full price.

No.
35 in 2022 and the CBA expiring in a year (plus the obvious), play out 2021, and then go from there. 

32 minutes ago, thxfrthmmrs said:

I'll be more hesitant if it's 2/$40M deal, mainly because I don't see him getting much more than that at his age, unless he improves even more. Also, you're removing flexibility to reassess next offseason and spending on other pitchers or areas of need, and taking on the performance and injury risk with little incentive. I'll definitely extend him at a discount, not when it's at or near full price.

A difference of $10M over two seasons? Sox have blown $10M on far worse signings in the past. A difference of $5M AAV shouldn’t have a significant impact on financial flexibility.

If the Sox can work out an extension, even adding a year or two on an option, the move becomes a home run.  Let's hope Hahn can still work some contract magic.

57 minutes ago, thxfrthmmrs said:

Hahn is typically good at extensions, but for rookies or pre-arb players. Lynn has already made his money so I see less incentive for him to accept an extension. Perhaps he would accept a discounted extension at 2/$30M to hedge against the performance risk due to age or switching to a different organization, but I really don't see a lot of incentive for him otherwise, especially accepting  a discounted extension.

He wanted an extension from Texas, per ken rosenthal

Truthfully, I'd like to see how he performs first

But, if he's as good as he's been the last 2 years, a 2 year extension would be nice

If he looks like he did with NYY, yikes