The Yankees now have 2 teams to compare themselves to - the Dodgers and the Mets, both of whom can and do spend over $200 mil a year.
Yankees: made playoffs 6 years in a row, 0 WS appearances, 3 ALCS, 2 ALDS, 1 WC. Random odds say they should've been in the WS at least once in that stretch, but otherwise not horrid or great.
Dodgers: 10 straight playoffs, 1 WS title, 2 WS losses, 3 NLCS, 4 NLDS. About what one would expect, again within reason of random odds.
Mets: just made the playoffs (new owner finally spending like the team is in NY) but knocked out in the WC round. Last WS win still 1986 (2 Dodger titles, 5 Yankee titles since then)

So basically the Dodgers & Yankees are pretty much random odds once in the playoffs. The 2 of them have combined for 1 WS title, 2 WS losses, 6 losses in the CS, and 6 losses in the DS plus 2 WC losses in the past 10 years (Yankees lost both and missed the playoffs 3 times). 17 playoff appearances, lets ignore the WC round for now. So 15 DS with 9-6 record, 9 CS with a 3-6 record, 3 WS with a 1-2 record. A bit better than random in the DS, but worse than random in the CS. Nothing out of the ordinary, nothing that screams 'they just don't care' or that a manager/GM needs to be fired.

The big question is why Cashman hasn't been resigned already for a 3-5 year contract. The Yankees first cracked $200 million in payroll in 2005, based on inflation the Yankees should be spending $300+ million now but are projected to be just shy of $200 million at Cot's right now but that doesn't include any of their free agents (Judge, Chapman, Britton, Tallon, etc.) They could sign 2 Aaron Judge's and still be below what they spent in 2005 (inflation adjusted). That is the difference between now and then.

"Sad" as in Cashman refused to boost Judge's price by vowing to re-sign Judge no matter what it takes?

By incredibly wealthy, high-payroll, virtually guaranteed to make the playoffs every year unless they turn into the Mets (never let children inherit a business) standards, the Yanks are in a tough spot.

C -- Trevino was unexpectedly good and could easily go poof next year and is turning 30 even if he doesn't go poof.
1B -- Rizzo is FA and turns 33. Abreu 36 and Bell 30 are the other FA options
2B -- Torres is comfortable above-average but not the star folks thought he might be. 2 years control
SS -- IKF is better-suited to utility
3B -- looks old, 1 year left
UT -- LeMahieu turning 34, 4/$60 left which is not a burden and so far so good
LF -- nada
CF -- Hicks and nada
RF -- nada or $350 M for Judge
DH -- Stanton had a tough year, mostly driven by a horrendous BABIP. But hey, he only missed 1/3 of it. 6/$160 left with $30 of that paid by Marlins.

That is not a promising lineup.

Cole is still a top starter but has 6/$216 left. A team option on Severino, one year control on Montas, two on German, three on Cortes. Could use a second stud but not an emergency. The bullpen is anonymous.

The bright side is a bunch of guys in the top 100 prospects.

CF -- Hicks and nada

Liek I've done before, you forgot Bader.

Or ... :-) I kid, Bader and Hicks ... also Stanton has 5/$160 left (or 6/$175)

I think it is noteworthy that the Yankees have been in the playoffs so often despite not drafting in the top half of the draft since 1993. Their highest pick since then was 16th overall in 2017 & 2015. Not bad to keep going without keeping the budget at the insane levels it used to be ($200 mil isn't what it once was). IFA has a cap so everyone (in theory) has the same opportunity. The Yankees are quite smart on that - in 2018 they signed 109 players via IFA (none have reached yet of course - these kids are 16 when signed after all). I think Cashman deserves a lot of credit and should go to the HOF someday as winning with a massive payroll is still winning and he has done that.

Cashman took over the Yankees in 1998, the year they won 114 games and the WS (11-2 in the playoffs). They won the WS the first 3 years he ran them, since that initial burst (thanks in large part to guys the previous people signed) they have made it to the WS 3 more times (1 win), and to the playoffs all but 4 seasons. A pretty damn fine record imo even though I'm a Jays fan. We had a HOF GM in Pat Gillick and got 2 WS at the end of his time here (his only 2 titles) and 5 playoff appearances with the highest payroll in MLB at the end.

This Judge situation feels a lot like the Cardinals - Pujols situation in 2011. Home team icon. Management would like him back but doesn't want to break the bank. Have to show fans they are making an effort. If you see the Yanks make a 5/250 offer, you'll know it's over. I'd bet a lot he ends up with Arte Moreno.

Judge just had his best year but I'd let him walk and buy younger, cheaper free agents. Get Diaz, Rodon and Correa/Turner (or both ). They'll be happier with the result.

I think Correa should clearly be the Yankees top priority, but he also should have been last season.

Mets: just made the playoffs (new owner finally spending like the team is in NY) but knocked out in the WC round. Last WS win still 1986 (2 Dodger titles, 5 Yankee titles since then)

I certainly don't think the slight was intentional, but you kinda forgot that the Mets won the NL pennant in 2015. to use your terms, "1 Mets pennant, 0 Yankees pennants since 2010."

not only that, but the Mets did it by utterly dominating a good Cubs team in the NLCS - winning all 4 games by 2+ runs, and iirc never trailing once in the entire series. the Cubs, of course, won the World Series a year later.

these columns tend to be in line with the Yankee fan base expectations, whether you guys think it's reasonable or not. they want pennants - and especially they want to win World Series. given their history, that shouldn't be very shocking.

Judge just had his best year but I'd let him walk and buy younger, cheaper free agents.

By OPS+, Judge just had the best age-30 batting season of anyone in MLB history. You don’t let such players walk.

You don’t let such players walk.

As always, it depends on price. If someone is going to give Judge 8/350, you let hit walk.

IMHO, this team should be going for a majoring retooling. Signing Judge to big dollars locks them into $100M plus p.a. for a long time, to an aging trio of Cole, Stanton, and Judge. Hard to see building a championship team around that past the next year or two.

The Yankees can afford Judge. They owe big money to Cole (worth it) through 2028 and Stanton (good, but not worth it) through 2027; they owe medium money to LeMahieu (worth it) through 2026 and Hicks (not worth it) through 2025. That's the entirety of their future commitments past 2023.

If the year-to-year payroll matters, it's simple enough to start Judge at a lower salary and then bump it up in 2026 when Stanton gets cheaper, and again in 2029 when Cole is off the books.

E.g. 9/$360 structured as $30/$30/$30/$40/$40/$40/$50/$50/$50 with opt-outs after 3 and 6 years. That's likely to be an ugly contract at the end but it keeps the Cole/Stanton/Judge trio to $98m annually to start and never more than that.

By OPS+, Judge just had the best age-30 batting season of anyone in MLB history. You don’t let such players walk.

Jason Giambi and Dick Allen are not far behind. The A's did let Giambi walk, and he got 7/$115 from the Yankees and gave them 22 WAR and 9 WAA. Would you give Judge the 2023 equivalent of 7/$115 if you knew that was the production you would get?

Allen was a completely different story. He had 2 very good partial seasons in 1973-74, 6.7 WAR in 813 PA, but he was finished after that. Plus he famously quit on his team in 1974. Played his last game on Sep 8 with his team right around .500. Yet he somehow managed to win the HR title.

If you could get Judge at the rates being discussed last spring, sure, but he's going to be so pricey it might damage the roster long term. He feels like a perfect fit for Moreno or Cohen

Seems to me a good and very obvious comp for Judge is McGwire.

MM 25-29: 142 OPS+, 38 HR/650, 4.9 WAR/650
AJ 25-29: 154 OPS+, 42 HR/650, 7.3 WAR/650 (about half of that gap is defense)

Judge better but at 28-29 Mac was giving hints of what was to come with 51 HR and a 184 OPS+ over about a full season's worth. The problem for both of course was staying healty -- Mac 2500 PA over 5 years, Judge 2370.

Judge's age 30 of course was historic while Mac's was very much not. But Mac's age 31 was a 200 OPS+ and a 60 HR pace but in just 422 PA. More of that at 32 in 548 PA, then he was fully healthy from 33-35 (mysteries abound!) and history was made. But from spring 1993 through spring 1998, a common refrain was "what if Mac stays healthy..."

So that's the big question for teams interested in Judge -- how much playing time do they get in his 30s. If you use Mac as the projection, he had 34 WAR from 31-37 in about 5.5-6 full seasons -- which is pretty awesome for those ages but you need to slap a price tag of $10-11/WAR to get to the sort of historic contract totals folks are suggesting for Judge. And can we honestly say our expectations are 3500 PA of 183 OPS+ and 345 HRs?

Mac of course put a lot of butts in seats. And Judge has much more defensive value meaning he doesn't have to match Mac's offensive numbers to match that WAR value.

The A's did let Giambi walk, and he got 7/$115 from the Yankees and gave them 22 WAR and 9 WAA. Would you give Judge the 2023 equivalent of 7/$115 if you knew that was the production you would get?

I think the answer to that might be yes. I'm not sure what the 2023 equivalent of 7/$115 is but I'm not sure it's more than 7/$230 ... I'm pretty confident it's not 10/$400 or anything. (By the way, Cot's says 7/$120) It's the same contract Beltran got a couple of years later. By 2009, Teixeira got about $22 AAV but 3 years after that Adrian Gonzalez stilll got $22 on his 7-year deal. Bryant just got 7/$182 ... even if a team went overboard for Giambi, would it be moreso than Rendon's 7/$245?

Rendon is tied for 5th highest AAV, 14th highest total. Years are a means of deferring payment so some folks behind him on the AAV list such as Lindor, Seager, Arenado could arguably be said to be paid more than Rendon. (I'd like to do it by age which I think would still show Rendon out front of those guys but that would take too much work.) So the equivalent of Giambi's 7/$120 is probably around $240 -- way more than Bryant, way more than Freeman. For 22 WAR that would be $11/WAR which I suspect is probably still a bit high but not bad enough a team would be severely disappointed.

Average MLB salary:

2002 - $2.3 mil
2022 - $4.4 mil
Using these numbers, the equivalent of Giambi's 7/115 would be 7/220.

Minimum MLB salary:

2002 - $300K
2022 - $700K
Using these numbers, the equivalent of Giambi's 7/115 would be 7/268.


The other option would be to look at some of the other superstar salaries of the time:
ARod: 10/250
Jeter: 10/189
Manny: 8/160
Hampton: 8/121
Giambi: 7/115
Based on these, I think you're still probably looking at 7/low-to-mid 200s.