Should the Sox have given Bogaerts a moderate extension?

[Kliq]

This was being discussed in the Bogaerts thread, but thought it would be good for a new poll question.

We were discussing the possibility that the Red Sox could have signed Bogaerts to a new contract extension before he hit free agency. Obviously, the San Diego offer was overwhelming, but could the Sox have signed Bogaerts to a comparatively moderate extension before Bogaerts hit free agency? @moondog80 threw out these terms:

How would you feel right now if they had done that and they were looking at 6 more years at 160 million?

Bogaerts first year in San Diego has been a disappointment, but at 3.7 bWAR so far this year he would be the second highest performing player on the Sox, behind only Bello, and has, at least by bWAR standards, out performed both Devers and Story, two guys the Sox have signed to big extensions. So the question is, how would you feel right now if Bogaerts was on the books for an additional 6 years and $160 million?

 

[John Marzano Olympic Hero]

Let me say first that: I think that the SD deal is insane and I'm glad the Sox didn't offer that and if you're Xander Bogaerts you have to take that offer.

However, I don't think it ever should have gotten to this point and Bogaerts should have been presented with a moderate (competitive) extension. He mans shortstop for two years (until Mayer is ready) and Story stays at second. Once Mayer comes up, Bogaerts shifts to third and Devers moves to either first or DH. Bogaerts plays a few more years at third, maybe transitions to first/DH and that's that. Kind of the Cal Ripken plan (aside from playing first and having days off).

 

[Big Papi's Mango Salsa]

I'd be absolutely on board for that deal to Bogaerts. This was a Lester repeat - it never should have gotten to free agency. Had we offered Bogaerts that deal literally the day after Story signed, I don't think there is any doubt he'd have taken it.

I mentioned this in another thread, but I think even as recently as the window after the completion of the 2022 World Series, the Sox could have offered Bogaerts something like 7/$185m and he'd have taken it (and I'd be more than fine with that deal too), let alone a more team friendly one.

Even had Story been healthy, they were looking at a gaping hole in the middle infield in 2023 and they're looking at one in 2024 as well (I think it's reasonable to assume, at worst, Story comes back as the 2.5 bWAR player / 3.5 bWAR player he was trending toward for a full season like he was in 2021). This says nothing of the need for a middle of the order RH bat to help ease in the transition for the prospects coming up.

Even if one assumes Mayer is ready in 2025 to take over SS, the idea of Bogaerts at any of 3b (with Devers the DH), LF or DH isn't unappealing on a reasonable extension, at least not to me.

 

[JCizzle]

Let me say first that: I think that the SD deal is insane and I'm glad the Sox didn't offer that and if you're Xander Bogaerts you have to take that offer.

However, I don't think it ever should have gotten to this point and Bogaerts should have been presented with a moderate (competitive) extension. He mans shortstop for two years (until Mayer is ready) and Story stays at second. Once Mayer comes up, Bogaerts shifts to third and Devers moves to either first or DH. Bogaerts plays a few more years at third, maybe transitions to first/DH and that's that. Kind of the Cal Ripken plan (aside from playing first and having days off).

Would you have been OK passing on Story to give Xander the money (plus ~$20M extra over the 6 years)?

 

[soxhop411]

Let me say first that: I think that the SD deal is insane and I'm glad the Sox didn't offer that and if you're Xander Bogaerts you have to take that offer.

However, I don't think it ever should have gotten to this point and Bogaerts should have been presented with a moderate (competitive) extension. He mans shortstop for two years (until Mayer is ready) and Story stays at second. Once Mayer comes up, Bogaerts shifts to third and Devers moves to either first or DH. Bogaerts plays a few more years at third, maybe transitions to first/DH and that's that. Kind of the Cal Ripken plan (aside from playing first and having days off).

we also have to remember his agent is Boras... So I wonder what it would have actually taken to get them to agree to sign

 

[Smiling Joe Hesketh]

I think had the option been there for Xander to get and accept a moderate extension, the Sox would have been happy to offer him one.

It would have been far more palatable than either the contract X got from SD or the contract the Sox gave Story.

But I think there was no reality where a moderate contract extension would have been accepted by Xander.

 

[moondog80]

Had we offered Bogaerts that deal literally the day after Story signed, I don't think there is any doubt he'd have taken it.

Really? None? Zero doubt at all that a guy with Scott Boras as his agent would have agreed on a moderate extension when he's one year away free agency?

I know he already did it once. And maybe he would have done it again. But I don't know how you can dismiss that Boras signed off on the first deal to secure that he'd be set up for life, but once that was in hand, would have strongly advised that he hit the market. They put that opt-out in there for a reason.

 

[John Marzano Olympic Hero]

Would you have been OK passing on Story to give Xander the money (plus ~$20M extra over the 6 years)?

I'm not sure that this is a binary option, I think that the Red Sox could have both players. They got Story at a discount. But in the spirit of the question, I'd take Bogaerts' last two years over Story's. I like how Story has looked defensively in the last six weeks, but his bat looks weak as shit. Maybe it gets better?

we also have to remember his agent is Boras... So I wonder what it would have actually taken to get them to agree to sign

This is a good point. But there have been instances when Boras clients have told him where they wanted to go. Does Bogaerts do this? IDK. The Sox didn't seem like they were serious about resigning him.

 

[Big Papi's Mango Salsa]

Fair enough @moondog80, one shouldn't talk in absolutes.

I think had Henry gone to Bogaerts the day after they signed Story and said "we value you more than Story and want you here for the long term, but we need to save money to extend Devers and build a World Series contender around you three, here is an offer of 6yrs and $160m" there is a 99.5% chance Bogaerts would have instructed Boras to take an offer that was $20m higher than both Story and Baez got in free agency and roughly $35m more than Ramirez took on an extension from Cleveland.

Also, agree with @John Marzano Olympic Hero that while they could have had both players, if I had the power to remove Story and his deal from the Red Sox and replace it with Bogaerts having the exact season in Boston he just did in San Diego and be "on the hook" for an additional 5 years and $133.33M (assuming my math is correct), I'd do that in a second - and I like Story and think he's going to be fine - but we could have (and should have) had both.

 

[Bob Montgomerys Helmet Hat]

I think had the option been there for Xander to get and accept a moderate extension, the Sox would have been happy to offer him one.

It would have been far more palatable than either the contract X got from SD or the contract the Sox gave Story.

But I think there was no reality where a moderate contract extension would have been accepted by Xander.

This is where I am. This was Xander's huge payday, it's why he had the opt-out. Why would he take a moderate extension instead?

 

[sezwho]

Really? None? Zero doubt at all that a guy with Scott Boras as his agent would have agreed on a moderate extension when he's one year away free agency?

I know he already did it once. And maybe he would have done it again. But I don't know how you can dismiss that Boras signed off on the first deal to secure that he'd be set up for life, but once that was in hand, would have strongly advised that he hit the market. They put that opt-out in there for a reason.

Yeah, I have no idea how some are so confident he wouldn't have signed the offer. I happen to think he would have signed a Story+ deal (6-7x25).

What is 100% certain is if you lowball/don't offer anything (lets call this the 'BoLester') when you have an exclusive window, you've played right into the hands of the agent that invariably wants to get to max value in a free market...which is water deeper than this (incarnation of) ownership swims in.

Would they have won an open bid for Devers? Of course not.

 

[grimshaw]

I would have maxed out at something like 6/180 though I was a big time Swanson guy. I'd love to know if there was ever any interest on either side.

 

[simplicio]

Nah, I love X but we got his best years and we've got more middle infielders in the minors than we know what to do with. Save the extensions for kids in their 20s.

 

[AB in DC]

Umm, they did offer a moderate extension. Back in 2019. I highly doubt X would have signed another one. He'd have been crazy to once SD put $280m on the table.

 

[jteders1]

This is where I am. This was Xander's huge payday, it's why he had the opt-out. Why would he take a moderate extension instead?

Well, it wasn't a moderate extension at the time. As noted above it was going market rate in the 22 off season, and was comparable to most big contracts out there. The market didn't go crazy until this winter. Bloom misread the market, and paid for it.

 

[brs3]

I wish the Red Sox would take a page out of the Braves playbook and sign good players to long contracts when they're young. That'd be super.

 

[8slim]

100% yes. The team would be better with X on it. And we could have jettisoned the flotsam that we saw trotted out at SS this season.

 

[ookami7m]

Sure of course we all would. But there aren't a lot of realities where that would happen

 

[The Talented Allen Ripley]

The moderate extension was the one he opted out of.

 

[lexrageorge]

Should be an option that says "there was no way Bogaerts would have accepted a moderate extension given the fact he just opted out of one".

We all wish there was a different outcome - doesn't mean such an outcome was at all plausible or even possible. But, yeah, it's Chaim's fault the Padres made an absurd overpay of an offer.

 

[Big Papi's Mango Salsa]

I suppose the question is what someone's definition of "moderate" is.

But I don't really think offering (as an extension) the 5th largest contract of the off-season is moderate. it's slightly better than market rate. Semien was the third largest contract of that off-season at 7/$175m; Story and Baez tied for 5th at 6/$140m.

I don't think of the 5th highest contract of the entire off-season as "moderate", but I think it would have been smart for the Sox to offer, and I do believe Bogaerts would have instructed Boras to take that offer. Maybe he'd ask for 6/$165 to beat out Freeman in terms of total dollars, and come in 4th. Not giving him this type of deal before the 2022 season was the huge mistake.

Not for nothing, but I will say that if there were any reports out there that Bloom offered him 6/$160m or even the exact offer Story got and Bogaerts said "no, I'm going to free agency" then I really don't think a lot of the people on this site complaining would be complaining. Sure, some would, but not me.

 

[Red(s)HawksFan]

I wish the Red Sox would take a page out of the Braves playbook and sign good players to long contracts when they're young. That'd be super.

I do think we want to define what the "Braves playbook" contract actually before we go too far down the road of should they/shouldn't they. Very few of the young players locked up by the Braves are signed beyond their age 30 season. Arcia, Harris, Albies, and Acuna are signed only through their age 30 season. Strider through age 31. It's only Ozuna, Riley, and Olsen that have multi-year deals taking them beyond that (each through age 36). Basically, to execute the "Braves playbook" you have to have a good number of sub-age-25 players breaking into the big leagues over a 3-5 year period.

The Sox aren't quite at that point with their current young talent yet. The only ones currently in similar positions to where the Braves players were are Casas and Bello. Devers is already on the Riley/Olsen contract. And Whitlock is already signed to an Albies-ish deal. I fully expect that Bloom will want to make offers to other young players, starting with Casas and Bello. Takes two to tango though. Hopefully the players are amenable. Not all of them are likely to be. We've seen it in past generations of Sox players. Papelbon insisted on going year to year and hitting free agency while Lester and Buchholz took Braves-style deals. Ellsbury insisted on going year to year and hitting free agency while Pedroia and Youkilis took Braves-style deals. Betts insisted on going year to year while Vazquez and Bogaerts signed Braves-style deals. The question is whether the next generation has any such players and which ones they will be.

 

[curly2]

Bloom has brought some very good position players into the system, but almost no pitchers. He got Whitlock, which was great, and Winckowski in the Benintendi trade, but there is little pitching in the minors now. In the Sox Prospects rankings, only four of the top 25 are pitchers, and just two, Shane Drohan (No. 13) and Yordanny Monegro (No. 25) came into the system under Bloom's regime.

The Sox really need Luis Perales and Wikelman Gonzalez to be good, but both have shown control issues in the minors, and there's a good chance neither ever sees the majors until 2025.

 

[Kliq]

Should be an option that says "there was no way Bogaerts would have accepted a moderate extension given the fact he just opted out of one".

We all wish there was a different outcome - doesn't mean such an outcome was at all plausible or even possible. But, yeah, it's Chaim's fault the Padres made an absurd overpay of an offer.

No, because the question is not whether you believe Bogaerts would have signed an extension or not. I understand why some people feel like that context is necessary, but the intent was to see how SoSH evaluated Bogaerts season so far this year, and how comfortable they would be going forward if we were paying him like a (comparatively) moderate extension would have paid him.

 

[tims4wins]

The moderate extension was the one he opted out of.

Yeah I'm confused here. The Sox already did this, didn't they?

 

[Lose Remerswaal]

Sure! And he’d have rejected a shorter term deal.

 

[LogansDad]

I wish the Red Sox would take a page out of the Braves playbook and sign good players to long contracts when they're young. That'd be super.

Well:

1) They kind of did that with Bogaerts back in 2019, and got him on a reasonable deal through his age 29 season upon which he had the ability to opt out. He did. They also just did this with Devers.

2) You need the players in the organization to do that. Obviously, not getting Mookie signed has turned into a disaster of rehash proportions, but other than him who are the younger players you would have liked to see signed to an Austin Riley, or even an Ozzie Albies type deal. I'll grant you Benintendi, possibly, but other than that there haven't really been any "must sign superstar youngsters" come through the system. Except Devers, who, again, they signed to a long term deal. Also, the Braves have been working on putting their current plan into action for a decade plus. It takes time.

I think Bello and Casas are really interesting case studies this offseason for what we can expect with the influx of minor league talent that is nearing MLB ready.

 

[Petagine in a Bottle]

I think the biggest problem here is the lack of young cost controlled pitching. The Red Sox had young, cost controlled players not that long ago - a ton of them, with Devers, Boagerts, Betts, Benintendi…..but what they didn’t have was any pitching, so they had to pay market rate (in terms of salary, prospects, or both) to acquire Sale, Price, Eovaldi, Kimbrel, etc.

The Braves have continued to roll our cheap young pitching (Fried, Wright, Strider, Anderson, Elder) which has allowed them to largely sit out the expensive and risky FA pitching marketplace. The Dodgers have done this pretty well too (Urias, Buehler, Gonsolin, etc. although they have spent on Kershaw and others).

So it’s awesome that the Sox have young position player talent- but if they re-up Casas and Mayer and whomever else but still need to delve into the Sale / Price / Nola / Yamamoto market frequently, they could find themselves in trouble if and when those expensive starters get hurt or are ineffective.

 

[Sausage in Section 17]

Sure! And he’d have rejected a shorter term deal.

Which is why, "I want a pony!" should be one of the poll options here.

 

[YTF]

The moderate extension was the one he opted out of.

Thank you

 

[LogansDad]

I think the biggest problem here is the lack of young cost controlled pitching. The Red Sox had young, cost controlled players not that long ago - a ton of them, with Devers, Boagerts, Betts, Benintendi…..but what they didn’t have was any pitching, so they had to pay market rate (in terms of salary, prospects, or both) to acquire Sale, Price, Eovaldi, Kimbrel, etc.

The Braves have continued to roll our cheap young pitching (Fried, Wright, Strider, Anderson, Elder) which has allowed them to largely sit out the expensive and risky FA pitching marketplace. The Dodgers have done this pretty well too (Urias, Buehler, Gonsolin, etc. although they have spent on Kershaw and others).

So it’s awesome that the Sox have young position player talent- but if they re-up Casas and Mayer and whomever else but still need to delve into the Sale / Price / Nola / Yamamoto market frequently, they could find themselves in trouble if and when those expensive starters get hurt or are ineffective.

Agreed, and they have added some interesting arms to the system, but none are likely ready until '25 at the earliest.

Bello appears to be at worst a solid 2/3 type, and has the stuff and makeup that could help him blossom into an ace, but when you have to supplement him with multiple $10M per year 4/5 types it ends up rendering the savings basically useless. They need some of these other guys to be able to fill in the back end of the rotation at minimum because having to buy 4/5th of a rotation on the open market is untenable.