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Thinking Breslow knows something we don’t. Kavadas has been an option all along but keeps getting passed on. It’s not like Breslow never heard of the guy…

So did Steve Matz. Should the Sox have gotten excited their ace was pitching like the guy at the back end of the last place Cardinals’ rotation? And the Sox gambled on Sale four times and lost each time. Why is it so difficult to understand they weren’t so willing to gamble a fifth time?

Fine, but still better than taking back a 32yo minor league backup catcher and saving (most of?) the $17mill that Henry likely wouldn’t re-invest anyway…

Oh they got a great deal on a rejuvenated pitcher. No one is questioning that. Breslow probably could have made them pay more money, but at least tried to get back actual baseball talent as opposed to a straight salary dump. Right now, that’s the only consolation Sox fans have with this deal..

That’s very possible. Supposedly a team inquired about Sale and was willing to take his entire contract in 2022, but Bloom declined because the return was negligible. Then Sale went for a bike ride and ended that. That unnamed team could have certainly been the Braves…

There is a long history of these immediate extensions becoming contingenies for players approving trades. It’s ignorant to simply says it’s incorrect when it’s a very distinct and likely possibility…

Varying degrees of success there. Evan White is the only glove-first guy on the list, and he plays an unusual position to reward a player for that skill…

There is almost no chance Atlanta gave a pitcher who has been averaging less than 40 IP per year an extension so quickly unless they had to. I suppose Sale could have been opportunistic and asked for more years or he wasn’t going to approvr the trade. Very unlikely Atlanta just extended him so quickly for no other reason…

Yes, getting Atlanta to take on more salary would have been better. But given Sale's performance the last few seasons, that simply did not seem likely. Unless maybe we took back evem less in return.

OK, but what should the expectation have been?

Disagree. Those bats are very consistent with runners on base. Unfortunately...

The lack of a report means nothing. Atlanta extended an oft-injured pitcher for 2 years long before spring training and only 3 days after the trade. This almost always means the extension was necessary in order to get the player to approve the trade...

Atlanta extended him 3 days after the trade, without seeing him pitch. Considering Sale's recent history, doesn't that seem a bit impulsive? When a player is extended so quickly after the trade (or has an option picked up), it almost always means that extension was necessary in order to get the player to approve the trade. Why else do it so quickly?

I think it was obvious this was solely done to cut payroll. No one is disputing that. But if given the choice on who to deal to cut payroll, would you have preferred the Sox dealt Sale? Or Jansen? Or Martin?

It's looks an awful lot like Sale was not happy with that and wanted either his option picked up or an extension. Certainly the Sox could have ignored him and let him pitch. But is flat out ignoring hm the best option here, too?

So $27mill is an acceptable gamble for a longshot? I still see people citing $10mill for Garrett Richards and Kluber as bad deals. And honestly, after 5 years since his last full season, with multiple injuries, what did you expect Sale's ceiling to be? If you say "obviously he was going to jump right back in and pitch like he did in 2017 and 2018," I'm going to (politely) call you a liar. Sale wasn't able to to that in 2019. Sale has posted 2.4 bWAR this year already. But no way in Hell did anyone see that coming after he posted 2.6 bWAR total from 2020 through 2023. What exactly was a realistic expectation of the "plenty to gain"?

OK. First of all, Glasnow is 30 amd his extension runs through age 34. Sale is already 35, Age is an important factor, right? Second, like Atlanta, the Dodgers can churn out minimum wage replacements to fill in the gaps in the event Glasnow misses time. If Sale went down in Boston, like he did in 2020, 2021, 2022, and 2023, who steps in? We don't have Gavin Stone, Emmett Sheehan, Landon Knack, Michael Grove, Dustin May. Heck, some of these guys are out with injuries of their own, but will be back before this extension ends. And third, there is a good chance that Glasnow extension results in a lot of dead money. What would be more surprising - Glasnow missing signficant time over the next 4 eyars or Glasnow staying healthy?

What made it a disaster was he did not pitch, and was ineffective on the rare days he did. Kluber also pitched 160 IP the year before the Sox signed him; Sale had thrown 150 IP total in the previous 4 years. Was he also going to be a $27mill depth signing? I am not saying the Sox came close to "winning this trade" or it is working out. But for the previous few years, every Spring, I would say the season hinges on Sale, and I always, always, always got the exact same 5 word response verbatim - "you can;t count on Sale." But now, after 4 years of almost no activity, the Sox should have coutned on Sale, based on events that did not exist at the time of the trade? Will we be having these exact same discussions every year? We have pitchers who simply cannot take the mound for Boston, and then go elsewhere and have success, as then suddenly we ignore their previous issues based on hindsight. Eovaldi, Wacha, and now Sale. Plus there was another factor with Sale that might be getting ignored. It looks a lot like he was interested in getting extended, or, at a minimum, having his option exercised. Should the Sox have done that in January? Tack on another full season to a pitcher who hasn't thrown one in 5 years? Atlanta played that smart, too, they gave him the extension it looks like he wanted so Sale would approve the trade. And it just happens to coincide in length with the (worst case) pre-arb years for Elder, Waldrep, Smith-Shawver, etc. They played it smart, because they had the depth to, unlike the Sox...

Handpicked? I can only name a handful of the multiyear extensions given to players so early. If you have other examples, I am all ears/eyes...

I know fans hate the opt out, because it means "if he is good, he is gone." In this case, it looked like some compensation. If they only wanted him for one year, that opt out meant they could offer him a qualifying offer, as it would be for roughly the same value, and he was guaranteed to reject it, since doing so would not only get him the same money from the opt out, plus more money from whatever his next deal was...

If he stays as a 1-1.5 fWAR CF, he probably makes a total of $6-8mill over the next 3 years (including first arb). But this extension does buy out 2 years of free agency. If there are any savings, that is the most likely place. An aging Keiermeier still gets over $10mill. I would imagine a 27-28yo Rafaela would top that in years and AAV. I agree it's a gamble, but I don't think it's a horrible one. The only issue us how it impacts the budget should they choose to also extend Duran or (eventually) Anthony, which might come sooner than expected given that we are seeing players like Chourio and Carroll get extended before they debut, or after a very brief one...

I like the idea of signing them early to cheaper deals and letting the ones that work out justify the ones that don't...

I saw an opinion somewhere saying the Sox should have given Bello's extension to Crawford instead. Speaking as a pro-Crawford extension guy, that is a remarkably impulsive call. By the end of the year, I would expect Bello to justify this extension more than Crawford would...

The bat-first players who got early extensions - Singleton, Kingery, Chourio, even Corbin Carroll - also all look questionable now or in hindsight. Paying for the glove is safer. But it's not unreasonable to question it, either...

Glove first guys are very cheap, and clearly they think he will be much more. But I think there is also the thought that he will be elite defensively even among the glove first guys. And some of those glove-first guys like Kiermeier are signing for a higher AAV than Rafaela, and those guys are on the downside of their careers. They could have waited, but if Cedddane did become even a league-average hitter, do you think he signs the same extension? I mean, he might. But I am not so sure his agent does not value him higher...