top of page
  • Cary Greene

How Far Away are the Yankees from Becoming a Contender?

by Cary Greene

August 31, 2023


After MLB crowns a 2023 World Series champion this season, one very good team will be sitting on top of the mountain and from Hal Steinbrenner's and the Yankees' vantage point, they’ll have to sit at the base said alp and gaze upwards, hoping for clarity of visibility so that the summit of the mountain can be brought into focus. He’ll have time to enjoy the sounds of the seagulls and dip his toes in the cool autumn waters that lap against Mount MLB and the first order of business will be to properly navigate the Rule 5 Draft.

Hal will have to hope his leadership team can avoid squandering away internal talent as they begin to assess what went wrong in 2023. Indeed, focusing is what Hal Steinbrenner will need to do prior to deciding to hit whichever button he’s contemplating pressing this offseason - be it the green restock one he hits every year or possibly the red rebuild one encased in glass that requires a fireman’s ax and the blessing of the Pope to approach and then shatter.

Objectively, the Yankees are MILES away from being prepared to climb the foreboding slopes of Mount MLB right now. There are treacherous crags covered with cawing Orioles and cackling Blue Jays blocking the vectors the Yankees might use on their next climb, not to mention formidable Rays are also waiting to try and slap them from their climb and send them spiraling into the frothy sea below.

What needs to be addressed and how much change needs to occur for Hal Steinbrenner’s marketing department to be able to sell the average Yankee fans and more importantly, the many important corporate sponsors, that the brand is one worth shelling out big bucks to support. Will the 2024 Yankees be a product fans and sponsors alike will want to be affiliated with? Or, is Hal Steinbrenner going to run the last place Yankees into the ground further?

Yankees fans have all offseason to contemplate the proper maneuvers the now irrelevant Yankees need to make in order to become relevant once more. Let's put into perspective how much change needs to occur and also, let’s set the bar where Hal Steinbrenner clearly hasn’t thought of positioning it. The Yankees goal shouldn’t revolve around limiting payroll in the name of maximizing profitability, as the brand was built because of how many championships the Yankees won. Without winning championships, the support base of the franchise will gradually wane.

Something Steinbrenner should rethink is that he should be doing everything he can to help increase the Yankees chances. If he doesn’t want to spend a lot of money, then he should hire a GM who can use the MLB Draft and the International Amateur Free Agency signing period to build a stronger farm system. Under Cashman, the Yankees farm system has slipped into the bottom third in the League.

Steinbrenner has been willing to spend big, but only here and there. He hasn’t grasped the importance of filling in a roster with quality balance and under Cashman, the Yankees haven’t traded well enough and they’ve done a poor job with free agency. With CBT penalties factored in, Cashman has created a last-place roster that requires Steinbrenner to pay a shade over $322.1 million. Suffice it to say that Brian Cashman is dramatically over-spending for the on-field results his cast of characters has delivered this season.

The Tough Questions

To put the current state of the Yankees in perspective -there are a number of questions to ask when determining how much the Yankees need to improve on both sides of the ball, in order to be a contender. The first two questions that needs to be asked are:

1. Does Brian Cashman truly understand the importance of pitching?

2. Will Hal Steinbrenner spend enough to fix Cashman’s mess?

I’ve written often that winning a championship starts and ends with pitching, so the answer to the questions above begin with who’s on the mound, not who’s on first! <chuckling> Since 1903, World Series champions have averaged a 113.48 ERA+ during the regular season. This year's team has put up a 105 ERA+, season to date.

Cashman’s Curious Strategy - A Repeating Theme

Cashman’s curious strategy has been to spend exorbitantly on two front-line starters, Gerrit Cole and Carlos Rodon, while also betting on the likes of Luis Severino and Nestor Cortes. Injuries have of course wrecked Cashman’s plans, as the starting rotation has largely failed the Yankees this season. Cashman has never been known for putting together fearsome starting rotations and it’s been a major stumbling block that has prevented Yankees teams of the past 14-seasons and counting from winning a championship.

Apparently Cashman favors a strategy of signing a few big stars and cobbling together the rest of the roster. This strategy isn’t working. The Yankees lineup is another example of Cashman’s philosophy, with stars like Aaron Judge and Giancarlo Stanton surrounded by below replacement level players at many positions.

Effect of a Decent Bullpen was Minimized

The bullpen, which has been arguably the fifth best in the game collectively, has only managed 65 Holds, season to date, which isn’t impressive but it’s likely related to not having to protect very many leads. This couples with Yankee relievers having a fairly low total of only 16 Blown-Saves. While a good closer would have helped the Yankees, it’s not like the Yankees had very many save opportunities, having recorded only 32 Saves thus far (19th in the League).

Starting Rotation was Knocked Out All too Often

What is apparent is that the Yankees starting rotation hasn’t been able to last deeply enough into their starts this season and they rarely gave the bullpen opportunities to protect leads. 21 percent of the Yankees payroll is committed to Gerrit Cole and Carlos Rodon, while only 6 percent of the payroll is committed to the Yankees other starters. The Yankees starting rotation has posted a 15.1 K-BB percentage (18th in the league) so they don’t strike out as many batters as they need to and they put too many runners on base due to walks and that’s given opposing batters too many chances to hit with runners in scoring position.

Breaking Down the Spending Problems

Factoring in the $17.7 million cost of the Yankees bullpen this season, which accounts for 6.3 percent of the Yankees overall payroll, Cashman is spending 33.2 percent (92.7 million) of the Yankees payroll on pitching. Glancing around the League, the Yankees spend the 5th most on pitching, trailing only the Rangers, Blue Jays, Astros and Padres.

Fangraphs rates the Yankees entire pitching staff 24th in the League having only amassed a cumulative 7.9 fWAR, they calculate that Yankee pitching has performed to an overall value of $69.4 million. Unfortunately for the Yankees, Cashman has spent 92.7 million on pitching, which means that Hal Steinbrenner has overpaid by $23.3 million for the results that Yankee pitching has produced on the mound this season.

Out in the Bullpen, Yankee relievers have performed to the tune of $24.7 million f-Dollars, with Cashman “only” spending $17.7 million on his relief corps. Therefore, the bullpen has more than done their job as they’re overperforming to the tune of $7 million.

What’s really hurt the Yankees rotation is of course injuries, but what has also been a nightmare is the lack of left-handedness. It’s difficult to win with a short porch in right field with a predominantly right-handed group of starting pitchers. The Yankees rotation has posted a 112 ERA Minus, which is an ERA stat adjusted for ballparks where 100 is average and lower than 100 is better. According to ERA Minus, the Yankees have the seventh worst rotation in baseball.

The Yankees pitching staff has allowed the fourth most home runs to left-handed batters in MLB this season. Opposing teams are stacking left-handed hitters in their lineups when visiting Yankee stadium, as it’s been a commonly themed game plan that opposing managers use the Yankees home field advantage against them. The Yankees starters have also given up the fifth most home runs in MLB this year (113) and that’s been a really big problem. The 334 earned runs that Yankees starters have given up ranks 17th in the League as well so it’s not possible to give Brian Cashman high marks for creating a championship caliber starting rotation this season.

Cashman often blames some of the Yankees woes on injuries and with the Yankees key left-handers, Nestor Cortes and Carlos Rodon missing the bulk of the season, there’s no doubt that Brian Cashman’s reliance on pitchers with injury risks has yet again left the Yankees dead in the water.

Not Enough Bang for the Buck

Breaking down the performance in the pitching department reveals that the performance of Yankees starters has been worth $44.7 million this season, which has only been worth 5.7 f-WAR to date. Yet Cashman has spent $75 million on starting pitching, which reveals a $30.3 million overspend on Cashman’s part. This means that the Yankees rotation is in dire need of multiple, high end free agent starters this offseason, if the team is to have any chance of becoming relevant enough to contend for a world series championship.

Because Cashman hasn’t built a rotation that’s not only worth the spend, but is durable enough to navigate a regular season, he’s not been able to give the Yankees stability where it matters most and this is reason number one that the Yankees have failed so miserably this season. I’ll write the words again: Pitching Wins Championships. Season after season, Cashman acquires too many starters with significant injury concerns and as an organization, the Yankees simply fail to produce high end help.

A Change in Philosophy is Needed

Given that the Yankees rotation always seems to suffer multiple injuries, perhaps it’s time for Cashman to consider shifting to a six-man rotation. That said, the Yankees probably need to invest in at least two, maybe three left-handed starters and they shouldn’t be shy about spending in order to bolster what is the most important area of the team.

Not only has the Yankees system has failed to produce quality starting pitchers, but Brian Cashman has weakened the Yankees rotation with poor trades, so the Yankees pitching depth has been scuttled by Cashman’s ineptitude.

The Yankees also need more left-handers in the bullpen and once all that is addressed, obtaining a solid closer might also help, but it’s hard to really fault the Yankees bullpen this season, they’ve been the lone bright spot on the team.

Free Agent Starters to Target

Starters with high ceilings are potential difference makers, but injury red flags need to be thoughtfully considered. A couple of attractive higher end left-handers headline the free agent class this offseason, in the relatively durable 30 year-old Blake Snell and the often injured but youthful 27 year-old Julio Urias. Jordan Montgomery is also available and he’d make a very solid back of the rotation starter if reunited with the Yankees.

It's very clear that Brian Cashman needs to really focus on left-handed starting pitching to give the Yankees a rotation that’s capable of making a deep postseason run. Hal Steinbrenner ought to insist on at least two left-handed starters being the top priority of the offseason. Free agent signings won’t fix the Yankees pitching issues, but using free agency to upgrade the rotation makes a ton of sense.

Meanwhile, the organization desperately needs to focus on converting pitching prospects into viable relievers. It would also be a tremendous help if the Yankees could draft or sign an international amateur or two who could become ace-level Big League pitchers. So far, the Yankees haven’t been very successful at doing this, which is why Brian Cashman will need to fix the systemic pitching deficiencies in the organization by utilizing free agency. With so many Yankees pitching prospects simply not being able to impact the team at the big league level, it’s kind of time for the Yankees to press the reset button with their farm system.

2024 Starting Rotation

1. Gerrit Cole

2. Julio Urias

3. Carlos Rodon

4. Blake Snell

5. Nestor Cortes

6. Clarke Schmidt

Positional Focus

Moving on to the positional side of the equation and speaking of moving on, finding a new home for Giancarlo Stanton and his full no-trade clause would be in my mind, offseason goal number one. Achieving a full salary dump would be the best case scenario if the Yankees want to focus on a left-handed bat or two. Even a partial salary dump would be fine in my book, as it would benefit the Yankees to part ways with the all too often injured Stanton as he enters the later years of waning career.

With Shohei Ohtani likely facing a second Tommy John surgery and given the Yankees disastrous issues with constant injuries to key players, I can’t fathom a scenario where the Yankees spend huge on Ohtani. Besides, the Yankees don’t need to add another single star player at the expense of rounding out their very one-dimensional, right-handed hitting roster.

Only 28-years old, Cody Bellinger makes a lot of sense if the Yankees pass on bringing back Harrison Bader, which they clearly ought to do. Amazingly, 26 percent of the Yankees payroll is spent on two outfielders (Aaron Judge and Giancarlo Stanton) while only 2 percent has been spent on the rest of the Yankee outfielders. This kind of spending is just utterly lopsided and not worth it, especially considering neither Judge nor Stanton can really stay healthy consistently - it’s simply a recipe for recurring disaster.

What the Yankees need is lineup balance. Opposing managers are throwing right-handed pitching at the Yankees at a near record clip this season. In fact, this has become a standard game planning mantra when facing the Yankees, since the Yankees have little to no left-handed hitters. Yes, the Yankees do have several outfield prospects like Everson Pereira and Jasson Dominguez, but the Yankees could surely use a couple of dependable reinforcements in the outfield.

Another available free agent who might make sense for the Yankees is Teoscar Hernandez. He’s an above average right fielder with good power. Granted, he’s a bit of an adventure when playing left field, but he could be a helpful veteran presence. If Cashman can move Stanton, he could pass on bringing back Bader and reshape the lineup a bit with the addition of both Bellinger and Hernandez. Coupled with Pereira and possibly a mid-season call up of Dominguez, the Yankees might look a whole lot better in the outfield next season.

Making a Trade or Two

Figuring out what to do with the few tradeable players that the Yankees have is another conundrum for Cashman to look at during the coming offseason. Any moves the Yankees make will probably be designed with an eye towards rebuilding the depleted farm system. This would be a dramatic jibe for Steinbrenner’s schooner to make, as in recent years it seems most trades wound up further depleting organizational depth in the name of acquiring players with one or maybe two years of team control remaining in attempts to win now. It’s time for a new course and a new way of thinking.

With diminishing team control factored in, the Yankees missed an opportunity to trade Gleyber Torres this season, but with a current $10.2 MTV per Baseball Trade Values, I don’t expect Cashman to continue to cling to Torres this winter as he could be used to add a quality prospect to the sagging system.

Along with the two key free agent signings above, the Yankees could certainly infuse the roster with some youthful exuberance next season. In addition to promoting Pereira, the Yankees will probably look to accelerate Austin Wells, Trey Sweeney and the aforementioned Dominguez. The second half of next season is a realistic time table to accomplish this, so the Yankees lineup might look a whole lot different in the not too distant future.

2024 Lineup & Bench

1. LeMahieu 2B

2. Dominguez LF

3. Judge RF

4. Bellinger CF

5. Hernandez DH

6. Rizzo 1B

7. Volpe SS

8. Wells C

9. Sweeney 3B

BENCH: Trevino C, Pereira OF, Florial OF, Peraza UIF



Sep 01, 2023

As has been said before, Hal thinks good enough is good enough. That's OK for any other team, but not the Yankees. Team needs to be SOLD!

Cary Greene
Cary Greene
Sep 01, 2023
Replying to

We can only dream about that! Cohen should sell the Mets and buy the Yankees.


Alan B.
Alan B.
Aug 31, 2023

This xite continues to crap out on me. Maybe I'll try later. Having 75% of my comment written twice, but site crashed is to watch the minors. Ben Rice already 1-1' R

Alan B.
Alan B.
Sep 01, 2023
Replying to

Trying this again. The free agent/money way is only a band-aid, does nothing to really solve the issues.

1) Make analytics a back seat driver, not a co-pilot;

2) On that theme, get real coaches who can teach real baseball stuff, not be a devoted disciple to the analytics;

3) The strength & conditioning guys have been here for 4 years, Cashman said not to bite their heads off in Year 1, but after no real change in Year 4, time to go. You know its bad when players (and former players) are openly talking about not telling the club about their injuries, and it's not being a tough guy thing;

4) Pitching in AAA has pretty much been a…


Aug 31, 2023

Nice piece Cary. Lots needs to be done. I Like some of your ideas. I am for keeping Gleyber. But overall, we are on the same page. Good info!

Cary Greene
Cary Greene
Sep 01, 2023
Replying to

Thanks EB. Regarding keeping Gleyber, my concern is that the Yankees badly overextended on DJ LeMahieu. I personally think it's time to play him at his natural position, which is and always has been second base. He can change games with his abilities at the kaystone and he's locked up long term. I don't think using him as a super utility player makes sense any longer, not with Orlando Cabrera around. Start LeMahieu and bat him leadoff or preferably, #2, hitting behind Dominguez in the second half of the 2024 season and yes, that means batting Judge 3rd where he belongs, not 2nd.


Aug 31, 2023

I would hope you Air-Mail this article to Hal Steinbrenner asap and I hope he reads your article and realizes Yankees can be fixed and still generate and give the faithful HOPE.... obviously Cashman is the problem as everyone but Hal knows. How does a outfield of Soto, Dominguez, Bellinger and Judge sound to you and Yankee fans? or lets get really creative.... by addition you have to subtract so Stanton, DJL Torres, and Schmidt, along two high prospect for Soto. The key is eating about 60% of Stanto'ss contract to movie him in the trade. He'll agree to and SD would be a perfect fit for him and Padres.

Cary Greene
Cary Greene
Sep 01, 2023
Replying to

Thank you JJ, we'll have to see what the heck the detached Steinbrenner does. He doesn't exactly make baseball decisions, but SOMEONE ought to at least advise him on what he's really getting for what is truly a substantial spend. Based on what he's paying for, theres very little bang for buck.


Aug 31, 2023

Great analysis, Cary. It comes down to two factors. We play half our games at Yankee Stadium. The ballpark screams for left handed batters to take advantage of the configuration and for Yankees' left-handed pitching to neutralize opposing teams' left-handed hitters. Cashman has ignored both historical compelling factors. Beyond that the rot in the minor leagues leaves us with no choice but to see if our best young players can perform in the majors. I like the idea of promoting Wells, Pereira, Sweeney, and Dominguez and giving them a large enough sample size to see if they belong. Don't Florial these four guys. Give them a real shot. Help them by replacing Boone and his coaching staff with former…

Cary Greene
Cary Greene
Sep 01, 2023
Replying to

Very good points Alan.

dr sem.png

Start Spreading the News is the place for some of the very best analysis and insight focusing primarily on the New York Yankees.

(Please note that we are not affiliated with the Yankees and that the news, perspectives, and ideas are entirely our own.)


Have a question for the Weekly Mailbag?

Click below or e-mail:

SSTN is proudly affiliated with Wilson Sporting Goods! Check out our press release here, and support us by using the affiliate links below:

Scattering the Ashes.jpeg

"Scattering The Ashes has all the feels. Paul Russell Semendinger's debut novel taps into every emotion. You'll laugh. You'll cry. You'll reexamine those relationships that give your life meaning." — Don Burke, writer at The New York Post

The Least Among Them.png

"This charming and meticulously researched book will remind you of baseball’s power to change and enrich lives far beyond the diamond."

—Jonathan Eig, New York Times best-selling author of Luckiest Man, Opening Day, and Ali: A Life

From Compton to the Bronx.jpg

"A young man from Compton rises to the highest levels of baseball greatness.

Considered one of the classiest baseball players ever, this is Roy White's story, but it's also the story of a unique period in baseball history when the Yankees fell from grace and regained glory and the country dealt with societal changes in many ways."


We are excited to announce our new sponsorship with FOCO for all officially licensed goods!

FOCO Featured:
carlos rodon bobblehead foco.jpg
bottom of page