r/redsox • • Dec 12 '25

Evaluating all the long-term (5+ years) deals Henry & FSG have given out

Here is all the long-term contracts that the Red Sox have given out since Henry bought the team in 2002. It doesn't include extensions that bought out arbitration years.

Player Age Years $ Bad Deal?
Edgar Renteria 30 5 $40M Bad
Jason Varitek 33 5 $40M
Dice K 26 6 $103M Not great
JD Drew 32 5 $55M
John Lackey 31 5 $83M
Carl Crawford 29 7 $142M Terrible
Adrian Gonzalez 29 7 $154M
Dustin Pedroia 30 8 $110M Pretty Bad
Pablo Sandoval 28 5 $95M Terrible
David Price 30 7 $217M
JD Martinez 30 5 $110M
Chris Sale 31 5 $145M Terrible
Trevor Story 29 6 $140M TBD, pretty bad so far
Masataka Yoshida 29 5 $90M TBD, pretty bad so far

The only great ones here are JD Martinez and Adrian Gonzalez, probably JD Drew as well. Can't really say Varitek was a bad deal but that's not a contract teams give out anymore. Price was definitely worth it, he was a workhorse for us for several years and the best Red Sox pitcher in the 2018 playoffs. But he was barely a replacement-level player for the final 3 years and they got a lower return on the Mookie trade because they salary dumped him. And John Lackey was worth it as well for similar reasons to Price, but he really only had one good year for Boston (he did net them Joe Kelly though).

But if you look at this list, there's more bad than good - and even most of the good ones didn't come without a decent amount of disappointment. It is a major reason this org is so reluctant to give them out to guys in their 30s. The majority of these bad contracts were bad due to injury and aging issues, which are much more frequent into a player's 30s. There is tons of data showing how steep the decline is for MLB players once they hit 30. As Bill James put it:

"The human body is like bread that won't stop baking. Age 33 is about the age at which you KNOW the bread is getting over-done and you wish that you could turn off the oven, but you just can't.”

I am also not counting Rusney Castillo (7 years $72M) because they were able to avoid that counting towards the CBT space by stashing him in the minors. But also a very bad contract.

Let me know if you disagree with my assessment of any of these contracts. Do you guys think the Red Sox have been particularly bad about handing out long-term contracts? Or is this just the norm of the MLB?

13 Upvotes

106 comments sorted by

70

u/[deleted] Dec 12 '25

[deleted]

10

u/rawspeghetti Dec 12 '25

Factor in the team friendly deal he had before and I'm don't regret a single penny Dustin got paid. Dude gave his body to this team and never took a play off. That's the dude you reward.

1

u/FC37 Dec 12 '25

Maybe.

There is quite a bit of revisionist history that the Machado slide was his sudden undoing. The truth is, Pedroia was probably starting to slow down at least a bit before that. Which is not a knock on him, it's what you expect as a 2B ages.

If he was a reliable 1-3 WAR player over the remainder of that contract, it would have been decent. But not terrific.

2

u/CryptographerFlat173 Dec 13 '25

Where was that slow down shown exactly? 5.4 WAR the last full season before the injury, 2.6 during that season

-16

u/Traditional_Half842 Dec 12 '25

He played a total of 9 games in the last 4 years of his 8 year contract, and didn't play at all in the final 2 years. He put up 10.6 fWAR over the course of that 8 year deal (1.33 per season). And his mounting injuries in 2017 clearly affected him down the stretch and in the playoffs where he was pretty bad.

The Machado slide obviously made things worse but Pedroia had knee issues before that slide and was declining athletically. The slide was just kind of the final nail in the coffin.

I'm not saying it's the worst on this list but I definitely cannot bring myself to say it was a "good" contract no matter how much I love Pedroia and loved the signing at the time.

15

u/Lumpy-Return Dec 12 '25

You’re not wrong in your technical analysis, but I’ll fight with “Trauma”. You’re signing Dusty to that contract, his sum was greater than the parts.

25

u/[deleted] Dec 12 '25

[removed] — view removed comment

-16

u/Traditional_Half842 Dec 12 '25

Great starting pitching is way way harder to acquire/replace than Pedroia's skillset was. The Red Sox won the World Series in 2018 with Eduardo Nunez as their second baseman. They most likely do not win the World Series if they replace Price with a replacement-level pitcher that year.

9

u/[deleted] Dec 12 '25

[removed] — view removed comment

-1

u/Traditional_Half842 Dec 12 '25

They don't even make it to the World Series without Price. He was good for them in the regular season and Sale got hurt at the end of the year and was a shell of himself in the postseason. They would've been riding with Edurardo Rodriguez and Eovaldi as their top starters if not for Price. He was a big reason they got the #1 seed and by far their best pitcher in the ALCS and WS.

19

u/[deleted] Dec 12 '25

Pedroia had 5.4 WAR in the 2016 season, his first healthy season after dealing with hamstring issues and getting his knee scoped. His 162 game WAR average from 2014-2016 was 5.1; his career 162 WAR average is 5.4.

Machado slid into him in April 2017, he played 89 games through the injury that season, still managing to put up a 4.0WAR/162 pace.

He was not in decline.

12

u/[deleted] Dec 12 '25

[removed] — view removed comment

-2

u/Traditional_Half842 Dec 12 '25

Pedroia did not make a single All-Star game in his 8 year contract. David Price was the best pitcher for the entire 2018 playoff run and gave them multiple years of top-end starting pitching (which is much much harder to acquire/replace than Pedroia's skillset).

2

u/CryptographerFlat173 Dec 13 '25

Imagine caring about the Pedroia contract, and not accepting a freak injury ended his career. He gave them multiple championships for dirt cheap money, I really don’t care he got paid later

39

u/[deleted] Dec 12 '25

[removed] — view removed comment

-2

u/Traditional_Half842 Dec 12 '25

Pitching is different from positional guys. I think positional players tend to age/decline the way you'd expect, whereas pitchers are more volatile. They can be great when they play, but are more likely to be unavailable altogether due to an injury.

I think Price is the perfect example of the kinds of contracts they should be willing to dish out. You are essentially paying a ton of money over several years in the hopes that the pitcher helps you win one championship in the front half of the deal. That is of course worth it, even if it screws you up financially a bit in the back half. But you do end up paying the price (no pun intended) once the player declines and has a bloated contract on the books but can't contribute.

10

u/[deleted] Dec 12 '25

[removed] — view removed comment

0

u/Traditional_Half842 Dec 12 '25

I'm applying different standards to starting pitchers and positional players because they are incredibly different commodities and they also age differently. You can win a World Series with a replacement-level second baseman. You cannot win a World Series with a replacement-level ace.

20

u/irwinian ortiz Dec 12 '25

All I see are a whole lot of names that helped bring World Series trophies home…

2

u/Traditional_Half842 Dec 12 '25

Excluding Story/Yoshida at the bottom (who have not brought a World Series home), 6 of the 12 names did not help the team win a World Series on their contracts. So about a 50/50 gamble at best on these contracts (and considering it's the Red Sox, that's probably the best conversion rate of any team in the league).

8

u/irwinian ortiz Dec 12 '25

My counter argument to that is that those two contracts were given out by the same guy, and there’s a reason he no longer has a job with the team. But ownership hasn’t even given Breslow a chance to spend, which has handicapped his ability to use his full set of tools to build the team. And honestly, 50/50 is pretty damn good in this league.

Also we’re ignoring the huge counterpoint here which is the LA Dodgers.

11

u/Rey_Titan Dec 12 '25

Pedroia wasn't a bad deal, super team friendly, fucking hate Machado

18

u/Jigs444 Dec 12 '25

This fanbase has become so pathetic.

10

u/flamingburrito5000 Dec 12 '25 edited Dec 12 '25

Yes, David Price was on a World Series team, but there's no way he was worth that contact. He got paid $50M more than the next highest player in team history, and he had one season above 3 WAR. FFS, we got rid of Mookie just to dump that contact.

6

u/Modano9009 Dec 12 '25

I remember Price's tenure as an immediate, sometimes dramatic disappointment. His 2018 playoffs (understandably) takes attention away from how awful that signing was over all.

3

u/Traditional_Half842 Dec 12 '25

That is part of my point - even the "good" contracts come with plenty of baggage. There are probably only 3 truly "good" contracts on this list - and a lot of people hated JD Drew's contract when he was on the team.

Also David Price wasn't just on a World Series team - he was the best pitcher for them for the entirety of the playoffs. That matters quite a bit. The entire reason you give a pitcher a huge mega-deal is so that he can help you win one championship. Price accomplished that.

2

u/flamingburrito5000 Dec 12 '25

I agree in general. If anything, I think you were a bit generous in the scoring (aside from Pedroia). Lackey was also bad (injured+beer and chicken) aside from the WS redemption. 

2

u/IKenDoThisAllDay Dec 12 '25

"aside from the WS redemption"

What's the ultimate goal if it's not to win the WS? He helped us do that. That's all that matters in the end.

Everyone wants to cope and say signing good free agents is bad actually and hurts the team yet we won the WS with these "bad" contacts on the books so it couldn't have hurt them too much.

2

u/Bostnfn Dec 12 '25

No free agent is worth the contract. It's about winning the world series. Price directly helped win that series, thus the contract worked out.

0

u/CryptographerFlat173 Dec 13 '25

Flags fly forever, and he was the true MVP of that World Series. The idea that this well-heeled a team needed to use their best player in most of our lifetimes to cut his salary is just plain stupid.

5

u/ObsoleteUtopia Sox fan since 1962, now senile Dec 12 '25

I had to wonder why the OP didn't write "good" or "great" into the ones that didn't suck. Seems like a negative way to start out.

Crawford was awful. I wonder if he was always an asshole and the Red Sox didn't do their due diligence, or if he just never should have been in Boston. But what a damn crybaby. Everything was always everybody else's fault. And he made Troy O'Leary look like Yaz out there.

But he wasn't as bad as Sandoval. I wanted to stick an apple in his mouth and serve him for Easter dinner.

There was never such a thing as a bad contract for Dustin Pedroia. It was an unfortunate contract because fuck Manny Machado forever until the end of time, but signing Dustin was absolutely the right thing to do. He worked cheap, too.

I'd call Price a good contract. There was always a worry with him - simply look at how many innings he pitched before the Sox even got him, and you'd have to wonder, not if, but when, his arm would have to be sent to the Smithsonian. The Sox needed a front-line pitcher, and they got one. And he was Julius Fucking Caesar in that World Series.

Sale was similar. I always thought he had an awkward motion and put a hell of a lot of strain on his arm, and there was a good chance he wouldn't make it through the contract intact, but I don't think anybody on earth would have predicted that run of wacko injuries that ruined the entire contract. And how many people on this sub were anticipating that he'd arise from the scrap heap in Atlanta and be Chris Sale all over again?

Rentería had a good career and that was a signing that looked good and should have worked. I don't know why he was so bad in 2005. He played on about 450 teams and I sometimes wondered if he was a guy you really didn't want in your clubhouse; but I never heard anything like that against him, I just thought it was strange.

Yoshi is a bad contract. I like him and think he's a good hitter, but he simply didn't fit into the team the way it was built and signing him was just lousy planning on Bloom's part.What makes me sad is that he's had some injury problems and the team kind of stuffed him into a refrigerator while they were supposedly building him up to play a left field they never intended him to play, and he won't have the MLB career he should have.

2

u/Traditional_Half842 Dec 12 '25

I had to wonder why the OP didn't write "good" or "great" into the ones that didn't suck. Seems like a negative way to start out.

The main reason I didn't assess the "not bad" contracts is that I know people will still complain about Price, Lackey, heck maybe even JD Drew - while others would point to their WS contributions to say they were great contracts. I personally would agree more with the latter but didn't want to start that debate.

There was never such a thing as a bad contract for Dustin Pedroia. It was an unfortunate contract because fuck Manny Machado forever until the end of time, but signing Dustin was absolutely the right thing to do. He worked cheap, too.

I mean, the reality is that they didn't get a good return on that investment. The circumstances are irrelevant; they paid an aging player a big long-term deal, and injuries derailed his career. The Machado slide sucked but Pedroia also probably would've had a much better chance of recovering from that injury if it happened to him at 23 instead of 33. He already had knee issues before that Machado slide, so it was like the final nail in the coffin. So that is my point - the risk is greater for these older guys than when they're younger.

Sale was similar. I always thought he had an awkward motion and put a hell of a lot of strain on his arm, and there was a good chance he wouldn't make it through the contract intact, but I don't think anybody on earth would have predicted that run of wacko injuries that ruined the entire contract.

John Henry probably knew there was a good chance. He said as much all the way back in 2014.

“To me,” Henry told me, “the most important thing this study shows is that virtually all of the underpaid players are under 30 and virtually all the overpaid players are over 30. Yet teams continue to extravagantly overpay for players above the age of 30.” I asked Henry to compare the Sox’ approach to that of the New York Yankees, who spent $500 million in the off-season. “It is a wildly different approach,” he said. “We haven’t participated in this latest feeding frenzy of bidding up stars.”

18

u/Prestigious-Action65 Dec 12 '25

There’s a frustration with the team not spending, which I understand. But what’s being missed is that these contracts aren’t just overpays—they make the team worse by eliminating flexibility and athleticism. The idea that you pay for the good years and swallow a couple bad ones at the end doesn’t hold up: the contracts are generally bad almost all the way through, at least from age 33 and onward. That’s clear statistically, but the raw anger is real, and OP is about to feel that, just like Flemming and Carrabis have recently.

8

u/Traditional_Half842 Dec 12 '25

Couldn't agree more. A lot of this subreddit subscribes to this fallacy that if a signing doesn't work out they can/will just cut bait and move on. There are almost no teams that operate that way and it's never been the Red Sox - and even when teams do do that, they typically have to struggle through a couple years of terrible declining play before DFAing / dumping the contract.

People act like the Red Sox are run the way they run their teams in MLB The Show where they can just sign all of their favorite free agents every offseason and then just dump the guys that don't work out (while eating the money) and spend even more money the next offseason on more free agents to replace the ones they dumped. That is not how things work.

13

u/Adept_Carpet Dec 12 '25

The problem is that player behavior has changed. David Ortiz signed a two year deal at 29.

No future Hall of Famer is signing a two year deal at 29 anymore. Above average players won't even do that.

In 2002, Henry and FSG were ahead of the game in a lot of ways, but now they're refusing to adapt and it's costing the team.

If we don't get some of these guys that only cost money, then we are locking in a return to the basement in 5ish years and limiting what we accomplish in the meantime.

6

u/Ensiferum Dec 12 '25

I don't understand the point you're making though. Is it that all free agency signings to long deals are bad? Or is it that the Red Sox are bad at it?

0

u/Traditional_Half842 Dec 12 '25

No I am not operating in binary absolutes saying "all" of anything is bad or good. I am saying there is obviously a lot of risk here that the org is gonna consider and they're not just gonna hand these contracts out like Halloween candy. Alosno is an example of a guy where the FO clearly felt the juice isn't worth the squeeze. There have been and will continue to be different players where they do feel the risk is worth it and give the aging player a long deal. We may very well see it happen with Bregman.

5

u/Ensiferum Dec 12 '25

Yes, that is all true and also very obvious. It's not even about Alonso. It's that they have felt this way about basically every big financial commitment these last years. And so they spend and perform like a mid-market team while squeezing every dollar out of the fans.

5

u/Dinobot2_ Dec 12 '25

So, going by your own assessment here, it seems like sometimes the contracts work out ok, and sometimes they don't.

If your prescription is that the Red Sox shouldn't give out contracts to free agents that are 5 years or longer if they're close to 30, then I think that is a bad prescription.

2

u/Traditional_Half842 Dec 12 '25

They currently have 2 of these contracts on the team right now. And they notably would not have won in 2013 without getting the Dodgers to take two of these contracts.

3

u/Dinobot2_ Dec 12 '25

Again, what is your prescription? Never sign someone close to 30 to a 5+ year contract again?

2

u/Traditional_Half842 Dec 12 '25

No of course not, and that's not the Red Sox prescription either. They have Story, they have Yoshida, they are prioritizing bringing Bregman back. But there is a balance and they're going to asses these situations on a case-by-case basis. They never have and never will operate like the Yankees where over half of their payroll is bloated contracts for aging/declining players, and they operate super deep into the tax. There are other ways to improve this lineup without committing $155M over 5 years for what are likely to be the worst years of this person's career to this point. There's obviously a chance a guy like Alonso is one of those dudes that does age well, but it's a huge gamble.

-2

u/Dinobot2_ Dec 12 '25

No of course not, and that's not the Red Sox prescription either.

Then why are you pointing out contracts that have failed if your prescription isn't to stop giving out these types of contracts?

0

u/Traditional_Half842 Dec 12 '25

Why are you operating in binary absolutes? I am saying that they of course will give some of these contracts out but they are not going to give them out to everyone. I don't see how that is hard to understand.

0

u/Dinobot2_ Dec 12 '25

Oh please, you posted this clearly to insinuate that either signing these contracts is a bad strategy and shouldn't be done or to do "Well, actually, maybe it's good the Red Sox didn't sign Pete Alonso."

I'm not operating in binary absolutes, I just think you're being weaselly.

0

u/Traditional_Half842 Dec 12 '25

You are equating me suggesting there's a reason they didn't sign ONE player (Pete Alonso) to a 5+ year deal to

your prescription is that the Red Sox shouldn't give out contracts to free agents that are 5 years or longer if they're close to 30

Those are obviously completely different things and you are treating ONE contract they didn't hand out as a binary absolutism. You are the one being weaselly here. I have made my point very clear - they are going to scrutinize these deals for aging players a ton and not hand them out like candy. Alsonso was an example of a guy where they felt the juice isn't worth the squeeze. There are other guys and will be more guys where they do decide to sign them.

1

u/Dinobot2_ Dec 12 '25

Ok there Jordan Peterson. "I'm just going to point out all the negative instances of a strategy that will naturally lead to the obvious conclusion that they shouldn't do that strategy, and then when someone says 'Oh wow, seems like you think the Red Sox shouldn't do that then?' I'll go 'What, no! I'm not saying that at all! Why would you think I'm saying that?'"

7

u/JaylenBrownAllStar Dec 12 '25

Yeah ownership has a real reason to hate over 30 players and most of these contracts will be scams in the last couple of years

However the Alonso one is not horrible for this offseason and they should still try and trade for Marte

2

u/[deleted] Dec 12 '25

Renteria slashed .285/.343/.402/.745 during that contract and played pretty good defense. Despite playing for 4 different teams. If we'd kept him and let him adjust he'd have probably played better.

As it was we flipped him for one of the best prospects in baseball and in turn flipped that prospect for a starter and multiple role players that helped us win a World Series.

Did Renteria work out in Boston? No. Was it a bad contract? Hardly. Leading off with a big miss puts the rest of the list in question.

2

u/theydoitforfreeXD Dec 12 '25

Gee I wonder if the Dodgers will be worried about how the Ohtani or Betts contracts look 5 years from now.

2

u/justaguynb9 Dec 12 '25

Lol at some of those numbers.

2

u/patricebergy Dec 12 '25

Statistics and projections of future value and player worth by salary are important, but you’re still missing the point that you have to spend to win. How many chips has this team won? How many have we missed out on by punting on good players rather than paying them? Mookie, Devers, etc.

The strategy you’re advocating for is smart, but that doesn’t mean you don’t occasionally burn some cash, especially when you have a top 4 revenue team, and are spending like a middle of the pack team a majority of the time. That is a detriment to the way this team could be run. The team shouldn’t explicitly be treated like John Henry’s investment portfolio, even if using those strategies does help prevent you from overpaying on the back end of contracts.

3

u/mosi_moose Dec 12 '25

Agree. The objective isn’t winning the most $/WAR title. It’s making the playoffs and advancing in the playoffs. There’s overlap in roster efficiency and winning for sure but like in any system if you run too lean your upside is limited.

3

u/Bostnfn Dec 12 '25

I'll add that the Drew, Dice-K, Lackey, Price, and JD contracts helped you win World Series, so I would rank those as good.

2

u/Traditional_Half842 Dec 12 '25

Yep I don't have any issue with any of those contracts - although there are definitely some folks who would still criticize the Lackey, Dice K, and Price signings.

My point is that these signings tend to be 50/50 at best - and even the good ones come with some drawbacks (the ones I mentioned). I think those contracts are still worth it - but you need to be selective and can't fill your whole roster with them.

2

u/mosi_moose Dec 12 '25

I appreciate the effort to list out the contracts and evaluate them. I think the right side of the ledger needs a lot more parameters to assess the outcomes. I’m not asking you to do this, but I’d be looking at metrics by age season like:

  • $/WAR vs league average
  • Key contributor to playoff run, WS win?
  • PAs or IPs
  • Days on IL

It’s also probably worth looking at trade vs FA acquisitions and extensions.

2

u/escapefromelba Dec 13 '25

Xander was a 5+ year deal but with player opt out. Don’t see Devers on here who was locked through his peak age range

1

u/Traditional_Half842 Dec 13 '25

It doesn't include extensions that bought out arbitration years.

1

u/escapefromelba Dec 13 '25

Devers deal didn’t buy out his final arb year  - he had a separate one year deal that did that.

1

u/Traditional_Half842 Dec 13 '25

I guess this is correct, I was thinking it was an 11 year deal but it was a 1 year deal immediately followed by an extension. But he's only 3 years into a 10 year deal, so we can't really judge it for this exercise anyway.

6

u/Snelly1998 Braised Beef Dec 12 '25

I know all i need to know from this one row

Dustin Pedroia 30 8 $110M Pretty Bad

6

u/Traditional_Half842 Dec 12 '25

What is that? He played a total of 9 games in the final 4 years of this contract, putting up 10.6 fWAR over 8 seasons.

1

u/Stercules25 Dec 12 '25

So he put up 10.6 fWAR at 2nd base over 4 seasons for $110M not terrible would be an overpay but wouldn't describe it as pretty bad lol

1

u/Traditional_Half842 Dec 12 '25

I wouldn't describe any contract where a player doesn't play at all for half the deal / 4 years as "good".

0

u/CryptographerFlat173 Dec 13 '25

Any career can end in a freak injury, sports contracts are all inherently risky, that’s not some great revelation. 

5

u/ectoboi20 Dec 12 '25

THANK. YOU. Yes, it’s exciting to sign guys and build the team, and it’s really annoying to hear we’re interested in everyone. However, you can go back through this Reddit and see people complain about each one of these contracts. People in baseball just age poorly sometimes, every team has these, but history shows when we do, it isn’t always wise.

2

u/stoolhandle Dec 12 '25

This doesn’t justify blowing up the core of Betts, Devers and Boagarts and getting nothing in return simply because you didn’t want to pay them

0

u/Traditional_Half842 Dec 12 '25

They didn't trade Bogaerts and the comp pick they got when he signed with SD was Kristian Campbell. Are you saying you'd rather the Red Sox have Bogaerts under contract for another 8 years and $200M?

3

u/stoolhandle Dec 12 '25

He hasn’t been great but if that means you don’t sign Story and Yoshida then fine he’s just as productive for the same cost. Compared to how big misses the other two are it’s not that big a win.

3

u/Pedrojunkie Dec 12 '25

When they were dishing out these contracts the Sox were consistently winning for decades. Since they stopped, they have been anything but consistent.

Causation or Correlation?

1

u/aceking555 Dec 12 '25

The Atlanta Braves basically never sign older players to long deals, but spend their money extending younger players. I think that’s what the Red Sox are emulating.

1

u/_drjayphd_ Dec 12 '25

Okay, but what if we regress all of the good long-term contracts to the mean?

2

u/wcgravy Dec 13 '25

Finally someone who doesn’t have faux rage

1

u/foxjohn2 Dec 13 '25

I think an inherent bias here is the fact that MLB's service time/arbitration rules basically make it so (unless you're Juan Soto with an OBP over 400 before you turn 20) you're not really hitting FA until you're 28/29 for the first time.

I agree with the idea that older players are more hit or miss and more injury prone, but this aint a real free market where you can go and just outbid the pirates for Skenes with a fatter wallet. Our only choices in the market are these older guys.

And I'll say it again, John Henry has more than enough capital to make this team a Dodger's style Death Star. Not doing so is a personal financial decision on his part.

1

u/MoeSzys Dec 13 '25

It's not just the Red Sox. Ever since Kevin Brown signed the first 9 figure contract back in the 90s, very few have worked out.

1

u/Illustrious-Yam-8722 Dec 13 '25

Hindsight is 20/20, but at the time I was just happy they weren't going to lose both Mookie & Sale.

I wasn't a big fan of giving Sale a long term deal at 31, but I also didn't think he'd basically be injured from the day he signed the contract until they traded him.

2

u/CryptographerFlat173 Dec 13 '25

But he had already missed the final 2 months of the season before they extended him a year early and always had a history of fading down the stretch, it was a bad idea from day 1

1

u/Jpgamerguy90 Dec 12 '25

Any deal can be a bad deal but that’s the way the cookie crumbles nowadays. You can’t be risk averse all the time and expect to win championships. When it comes to free agents they’re all more than likely gonna be at or approaching 30 so unless you never want to sign a premium free agent again (basically becoming a team that is no longer a real title threat) or are ok handing out 10 year mega deals to the occasional 25/26 year old who manages to make free agency you gotta take a risk.

Hell factor in all the money they pissed away on bad 1 years deals they could have another legitimate starter in their rotation or another big bat. By playing “smart” the Red Sox have still been foolish

5

u/Traditional_Half842 Dec 12 '25

They aren't totally risk averse, but they are never ever gonna operate like the Yankees where they have a bunch of bloated contracts for aging players on the books and are super deep into the tax. They never have operated that way and never will. They do spend some money on aging players - they have a good amount of money allocated to Story and Yoshida, and they are prioritizing bringing Bregman back. So if they're gonna spend a ton of money on an older free agent, they're gonna be very selective and only do a couple of times. There are other ways to improve this lineup without committing $155M over 5 years for what are likely to be the worst years of this person's career to this point. There's obviously a chance a guy like Alonso is one of those dudes that does age well, but it's a huge gamble.

1

u/cntodd Dec 12 '25

Pedroia would have been just fine, if not for douche McGee.

1

u/Traditional_Half842 Dec 12 '25

But the reality is that he wasn't and that aging players have a harder time recovering from injuries like that than younger guys. Pedroia had already had knee problems before the Machado slide (again - something that is much more common for 30+ year olds).

If ifs were fifths then we'd all be drunk. I am just posting about what actually happened with these contracts.

1

u/ltdm207 Dec 12 '25

Now compare this to the players you excluded. You don't have a control here to compare to. Perhaps the proper conclusion isn't "contracts for guys over 30 are bad", but rather "projecting future performance is volatile, and most players decline over a 5 year window".

2

u/Traditional_Half842 Dec 12 '25

I included a detailed study that shows player performance peaks in the 20s - and the descent when a player enters his 30s is much much more rapid than the ascent in his 20s. Player production steadily increases around ages 21-27 and peaks at age 27-28. On average by the time a player hits 31, he is less productive than he was at 21 (his least productive year in his 20s).

1

u/Extreme-Balance351 Dec 12 '25

Anytime you sign a 30 year old player to a 5+ year deal you know there are going to be bad years. But you are banking on the first few making it worth it. That is the price of doing business. Noticed you didn’t mention that 8 of these players were key contributors on World Series winning teams

1

u/Traditional_Half842 Dec 12 '25

Noticed you didn’t mention that 8 of these players were key contributors on World Series winning teams

Only 6 of them were - Varitek, Drew, Dice K, Lackey, Price, and JD Martinez. Pedroia and Sale won all of their WS before the deals listed here and they weren't very impactful across these deals. Chris Sale's deal was one of the 3 worst contracts in all of baseball for the 4 years he was in Boston.

So even if we exclude Story/Yoshida, it's 6 of 12 players listed or a 50/50 gamble. And I'd bet that's one of the better ratios of any team in the league considering how many WS the Red Sox have won in this timeframe.

1

u/Stercules25 Dec 12 '25

We have a bad hit rate on our longer deals, that is more than fair, but I couldn't disagree with you or Bill James more regarding that quote you added. For proof I'd say look at the home run leaders this past season and their ages (outside of Cal).

If we aren't willing to give players an extra year(s) then we have to give them more AAV but we aren't willing to go deep into the CBT so we won't do either. The Red Sox could have signed Pete Alonso (or maybe even an older Schwarber) on a 1 year deals if they wanted to pay ~1.5-1.75 years of salary for the 1 year. We aren't willing to do that. So don't know the point you're trying to get at

1

u/Traditional_Half842 Dec 12 '25

I couldn't disagree with you or Bill James more regarding that quote you added.

I mean the empirical data agrees with Bill James and disagrees with you.

1

u/Stercules25 Dec 12 '25

What's the empirical data of modern day

1

u/Traditional_Half842 Dec 12 '25

The study I linked is less than 2 years old. This is more of a gut feeling but it seems like the aging curve is only becoming more prominent - not less. Copying from this post yesterday:

In 2025, there were one hundred and thirty seven position players who logged 2.0 or more bWAR. Not a crazy benchmark. How many of those players were aged 35 or higher?

Three. George Springer, Freddie Freeman, and Miguel Rojas---that's it. In other words, it is a virtual guarantee that a position player aged 35 or higher will not perform at a high level in the majors.

Maybe you think I'm cutting off too high. Okay, how about aged 33 or higher? Only thirteen achieved 2.0 bWAR. And of those thirteen, only one was in the top twenty five: Aaron Judge.

2

u/sktchld Dec 12 '25

Putting Dustin as bad isnt really fair.

-1

u/Traditional_Half842 Dec 12 '25

He played a total of 9 games in the final 4 years of this contract, putting up 10.6 fWAR over 8 seasons. I wouldn't call that a "good" contract. Would you?

2

u/sktchld Dec 12 '25

Take all context out of it sure. It was a bad deal. He didn't ask for Machado to end his career and you don't plan for it during negotiations. Dustin would have lived up to it.

-2

u/Traditional_Half842 Dec 12 '25

I mean, the reality is that they didn't get a good return on that investment. The circumstances are irrelevant; they paid an aging player a big long-term deal, and injuries derailed his career. The Machado slide sucked but Pedroia also probably would've had a much better chance of recovering from that injury if it happened to him at 23 instead of 33. He already had knee issues before that Machado slide so it's disingenuous to pretend that that was his only issue - it was more like the final nail in the coffin. So that is my point - the risk is greater for these older guys than when they're younger.

-3

u/Enough-Remote6731 Dec 12 '25

The hive mind here is that none of this matters.

5

u/Dinobot2_ Dec 12 '25

The hive mind is correct.

0

u/Enough-Remote6731 Dec 12 '25

A lot of knowledge here.

-1

u/OkGo_Go_Guy Dec 12 '25

Story has been a fine contract.

3

u/CryptographerFlat173 Dec 13 '25

2 lost seasons, one pretty good season and the first one was half lost as well, it has not been a fine contract 

0

u/MoeSzys Dec 13 '25

All anyone remembers about Price is the 2018 post season. That contract was a huge bust. 11 WAR over the entire 7 years. At his best he was a good middle of the rotation, 5 of those 7 seasons he either didn't pitch or didn't pitch well

2016 - ate innings but with 3rd starter stuff at best 2017 - solid, but only 72 innings 2018 - pretty good, not even close to an ace 2019 - mediocre 2020 - didn't even pitch 2021 - lousy 2022 - mediocre out of the pen

1

u/Traditional_Half842 Dec 13 '25

The way I look it as that all long-term megadeals like that come with a lot of risk and there's a good chance the back end will be bad. But the goal of the deal is to have the guy help your team win a championship in his first few seasons while he's still in his prime. Price did that and was literally their best pitcher for the entire 2018 playoffs. That makes the contract worth it. Why else do you give a player a big contract other than trying to win a World Series?

0

u/MoeSzys Dec 13 '25

But he wasn't very good on the front end either. He had one pretty good season

Even in the post season he wasn't a wizard. He got shelled in the ALDS, and was pretty good in the ALCS. His World Series line is very good, but a lot of that was luck because his FIP was double his ERA

1

u/Majestic_Seagull_87 Dec 13 '25

Sorry, but Chris Sale won a Cy Young on that contract...

0

u/Traditional_Half842 Dec 13 '25

He was never healthy for October baseball a single year on that contract.