Greatest owner ever…? Hardly.

George Steinbrenner (left) and Billy Martin (right) didn't always get along

They say that money can’t buy happiness. Well try telling that to New York Yankee fans.

In 37 years under George Steinbrenner, the New York Yankees won 7 World Series titles and 11 pennants. In 1973, Steinbrenner turned a $10 million investment into a franchise that is now worth an estimated $1.6 billion.

Following his death yesterday, the baseball world has been buzzing at the tragedy but also about the legend that is George Steinbrenner. Despite the fact that Steinbrenner made the Yankees into perennial contenders, there is much reason to believe why he should not be considered one of the greatest owners in the history of sports.

George Steinbrenner is probably best known to the casual sports fan for his outrageous spending on top flight players. But he is also well-known for his constant hiring and firings of his employees.

7 World titles in 37 years seems like a lot of championships, but when you think about it, with that much money being thrown around they probably should have had even more.

As I mentioned above, George Steinbrenner is not one to shy away from spending his money. To this day, the Yankees do not care about spending above the “salary cap” and paying a bit of a luxury tax. They are willing to trade money for championships and that is something that you have to give George Steinbrenner a lot of credit for. It is a path that should be taken more often by owners because what is really the difference between having $300 and $200 million?

It is frequently overlooked that the Yankees had a championship drought for 17 years (1979-1995), which goes to show that ludicrous spending and instability in a franchise is not always going to be the answer to winning championships.

If you look at the years when the Yankees started winning again, it was not just because they were buying all their players. It all started again when the front office decided that the Franchises insufficient development of talent through their system was not getting the job done, and it was time to start bringing up players through the minor league ranks.

Think about it, throughout the last 14 years there have been four core players that are still to this day high quality major league players. Derek Jeter, Mariano Rivera, Andy Pettite, and Jorge Posada. What you have there is the four most important pieces of any team. You have a starting shortstop, starting pitcher, closer, and first-string catcher.

Those four guys have been a constant among the Yankees organization and are the primary reason why they have won so many championships. Let’s not forget Bernie Williams who was the starting center-fielder for the better part of ten years.

I do realize that the money that the Yankees are able to spend allow them to surround this nucleus of players with other star guys. When you get star players like Hideki Matsui, Jason Giambi, Johnny Damon, and Alex Rodriguez it is going to be difficult to lose, but the fact of the matter is that the Yankees had a core of guys that they could build around. The Yankees winning formula does not alone stem from George Steinbrenner and his massive spending ways, but it sure doesn’t hurt.

It’s not like the Yankees didn’t buy players when they weren’t winning championships. They brought in guys by the names of Ricky Henderson, Steve Sax, and Dave Winfield who were all unable to deliver the city of New York a championship.

Do you seriously think that Yankees are going to win the same amount of games without the best closer of all time or without the clutch play of Derek Jeter?

Speaking of stability, Joe Torre was only around for oh…11 years, which is the longest tenure for a manager during the George Steinbrenner era.

Contrast that to Steinbrenner’s first 23 seasons as Yankee owner where he changed managers a total of 20 times, which included Billy Martin being fired and rehired 5 times. He also switched general managers 11 times in 30 years. Please do not try to tell me that that kind of instability is not going to hurt a team.

What if you had an owner who had the exact same spending style as George Steinbrenner without all the craziness to go along with it? What if that same owner decided that he was not going to meddle in the affairs of his front office? What if this bizarro Steinbrenner was instead the owner of the New York Yankees?

What you would have is a New York Yankees franchise that would have, in those same 37 years, a greater than or equal amount of championships than the real George Steinbrenner has brought to the Big Apple.

George Steinbrenner may have done a lot of great things for the New York Yankees but he is by no means the greatest owner of all-time.

Agree? Disagree? If you have any questions, comments or suggestions, please feel free to reply in the comments section below. Or you can e-mail me at I’m now on twitter follow me @paintstheblack and I will gladly return the favour.

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About Chris Ross
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32 Responses to Greatest owner ever…? Hardly.

  1. kramerj7 says:

    Very well written post. But I disagree. 7 championships in 37 years is pretty darn good. Name me a team during that 37 year span that has won more than 4 World Series..

    The man will be sorely missed and he is the one who made Derek Jeter a Yankee and made him the greatest winner of generation. But you are right in his outrageous spending and the playoff drought. Nobody can argue with the results since 1995 though. He started out well, and then had a major drought. But boy did he finish strong.

    George, probably the most well known professional sports owner of all time will be missed.

    Check my blog at


  2. kwsports says:

    im not too big on baseball, but your title makes you look very anti-Steinbrenner. The man died with a legacy. I’d let him have that. On the other hand, like I said, I don’t know much about baseball, but 7 championships during his run sounds like a great number.. My main concern is your title.. “Greatest owner ever?… Hardly” makes it seem as if you don’t think he was a decent owner at all.

    The writing was great, but I’m not too sure if I agree with your post or not.
    Keep it up though.. I’ve been busy so I haven’t posted in awhile, but I’m back now.

    Check it out later on, at like 7ish

  3. Steve says:

    I have to disagree with KWSPORTS.

    The title is what draws the reader to read more, especially if you disagree. Steinbrenner fans will immediately look to see what you are saying about the legend. People who are anti-Steinbrenner will come to see what arguments that they can add to their arsenal.

    But, there is more to the article than the title and I enjoyed it. Some might say that they won in spite of George, because during his banishment, the methods used by the Yankees changed from the buy everyone approach to attempting to develop some home grown talent.

    That and Seinfeld….

  4. tophatal says:


    Steinbrenner duped the citizens of New York. How many of the residents there can actually afford to attend the games let alone purchase tickets and concessions ? The one thing I can’t doubt the guy for was his heart in terms of his philanthropic efforts as it concerns kids, the families of fallen police officers and military servicemen .


    Alan …….. 🙂

  5. Chris:

    Nice blog. The Steinbrenner big buck approach to winning is being copied by virtually any owner who can do it. Look at the NBA. The LeBron “decision” is indicative of the need for any good team to have a core of 3 big stars no matter the cost. In the NFL, Dan Snyder tries to emulate Steinbrenner but is not as good a judge of talent. Sports are definitely big business — but still alot of fun for alot of people.

    Keep up the good work.

  6. swithbeatz says:

    I think Steinbrenner’s greatest gift has been his willingness to spend. He’s shed light on the fact that many of these owners pocket many of the profits that their big league team brings in and never reinvests it in their own franchise. Steinbrenner wanted to win just as badly as you or me and that’s why he was well remembered. Its the other things that made him a jerk but you can’t discount what he did.

    Good job Chris.

    I wrote about this as well.

  7. redtreetimes says:

    Good post. While I disagree that 7 titles in 37 years is not great achievement, you are absolutely right in how Steinbrenner assembled the core of his his most prolific group–Jeter, Mariano, Posada, Pettite and Bernie. He spent an awful lot of money on keeping these players, probably more than their true market value. But he knew something, a lesson learned from his past failures such as the 16 year drought, that it was important to create a new tradition. A tradition based on settling for nothing less than being number one. And getting the players and fans to believe that they deserve it. And that’s what these guys have provided to the team and fans.

    That being said, who is a better owner in baseball?

  8. Seriously, Chris? You’re fighting a losing battle with this one. He kick started his NYY legacy with big spending (Hunter, Jackson) and put the crowning touches on it the same way. In between, as you say, he built a dynasty from within – he deserves credit for this, too, as it happened on his watch.

    Seven championships and 11 WS appearances in 38 seasons. He also forced renovations at the old Yankee Stadium, built the new one, and oversaw the creation of the most culturally influential juggernaut in sports… Suggesting that he underachieved in some way is just ludicrous.

  9. DukeofWagner says:

    Chris, thanks for reading my tribute to the Boss. You make a great case and cite a lot of facts that I can’t argue with. Obviously, I have a different viewpoint. I wrote my post for all the people that see the Boss as you see him. Its like all the Boss haters out there think there is a salary cap in baseball. Well just like steroid testing in the 1990s, it doesn’t exist. So we can all speculate about how the Boss would have done with a cap just like we can all argue about who the real stars are vs. the chemically aided stars. In both cases you have to deal with reality. And the simple fact is, the Boss was just better at it than anyone else working within the system that existed at the time. That’s all that matters.

  10. iammattfried says:

    Hey Chris:

    Good points made, but I would also argue that, yes – the farm system is what ultimately made the Yankees great; however, it would not have gone in that direction without final approval of the owner. Steinbrenner’s first stint as owner (which I call The Iron Curtain Era) was riddled with power struggle, and contributed heavily to The Yankees decline, as well as 1 year ban in 1992. It was only after he learned how to loosen the reins (and solidify his executive role) that the farm system improved, and allowed players like Jeter, Posada, and Rivera to develop. Once he finally figured out how to make the most of his owner role, without creating a corporate autocracy, THAT was the key to the Yankees’ consistency. That’s also a lesson that guys like Dan Snyder still don’t get it.

    Keep it going, dude.

  11. yahdigg says:

    great read! i have to disagree somewhat though, respectfully. what he did with the yankees, i don’t think any other owner for any other sport would have even come close. the yankees hold the sole spot as being the team in ALL of history in ANY sport to have TWENTY-SEVEN world titles, if you ask me that’s a pretty big accomplishment! not the Lakers, not the Jets, no other team in any sport even comes close. people will always disagree with any boss of any company, but at the end of the day, what people have to realize is that that boss created a “something” from “nothing”. I’ve experienced it with my dad ever since i was little. sure, there were people that hated him and thought that he cared too much for his business, but the bigger picture was that he made his business SUCCEED and if he didn’t care, then who else was going to? and that’s what George Steinbrenner embodied. as they say, “when you’re at the top, not everybody’s going to like you!”. people all over the country know what George stood for, and how hard he worked to build a team that could win championships and be the pride of New York. even people that weren’t into baseball, you would mention George’s name and they would immediately say “Yankees”. my grandma, who’s too old to watch sports, even know who he is and what he stood for! & as far as other teams in baseball always hating him for taking the good players because of the elasticity of his bankroll, George WORKED for it! It’s not like he won the lottery and was just pulling playing for the hell of it not even knowing their stats! i have great respect for that man. fine business man. to find another like him in our lifetime is going to be hard! he makes me proud to say i’m from Newww Yorrkkkk! long live The Boss! Once again, i commend you on this fine post! 🙂

  12. Nice one.

    Whether he’s the greatest owner of all-time or not will always be debatable—somethings can’t officially be determined. I’d put him in the top 3 though—right behind John Henry and Rachael Phelps (Owner of the Cleveland Indians in the film, Major League)…


  13. I think what separated him from other “tyrannical” owners (say, Jerry Jones) was his ability to create a fine balance between the strength of his ego and the demands it imposed on others–typified by the lion’s share of his championships coming near the end of his reign. Sure, there was plenty he did to “buy” those victories (tophatal alludes to high ticket and concession prices), yet the results are what they are.

  14. Andrew Sharp says:

    Good point at the end. I’d say the players won the championships and George the owner caused a lot of chaos. A better owner would sit back and let the GM run the office.

  15. nycpenpusher says:

    Hi Chris.

    Certainly your lament about how Steinbrenner was just trying to “buy” championships isn’t anything new. And maybe those sorts of comments are justified in a way. But let’s look at it from the perspective of the sport as a whole.

    Owners are earning money from their franchises because people are willing to buy tickets, merchandise, and food at their parks. But if the fans don’t come, the sales don’t get made. Steinbrenner was not just about winning, he was about making lifelong fans. He wanted to have the best players because it meant people would be enthusiastic about the team! And so he was willing to shell out more because it meant more excitement!

    Sure, everything could have stayed the same, with owners skating by with their talent at average levels, but Steinbrenner was investing in the sport! When the Yankees come to town, whatever town you’re in, you will see stars. That boosts the gates for all teams. That also increases interest in the sport itself, which makes more profits for everybody involved. So don’t think that the Yankees were the only ones to profit. If the other owners were all that against it, they would have stopped it long ago.

    Steinbrenner had a flair for the theatrical, and back in the early days didn’t mind making a lot of noise, and shaking things up if he didn’t like what he saw. And he knew that would get headlines, and it all worked towards making more people interested in everything baseball. Ultimately, I see him the same way as Bill Veeck and Charlie Finley… all of them had an element of P.T. Barnum in them, and all of them are, to my mind, legitimately great.

    And if you want MY take on Mr. Steinbrenner, you can find it here:

  16. chappy81 says:

    I think Steinbrenner was good for the game in some respects but bad in other ways. I think every league needs a villain, and he made the Yankees that. I think we have a new villain in the NBA now with the Heat or at least for the time being 🙂

    For better or worse he changed the game and should be remembered for only accepting perfection even though if he ran his team like a communist. Keep up the good work man!

  17. Sriram says:

    He put money into the product. He spent, but he also invested. The growth of the Yankees brand was due to him. Beats Charlie Finley trying to sell his players for nothing. The Yankees used their biggest advantage – being the New York Yankees – to great effect. That his baseball people have developed the franchise since the fallow days was a happy accident. His values as an owner were unparalleled. I hate him – but his print on the game needs no explanation.

  18. popularjunk says:

    As I stated before. He was definitely a mogul in the city of New York. Everyone has their time. The thing is, if everyone is prepared for it. I will definitely check out you site. and give you my opinion, keep visiting mines i always have a good word for you there. http://WWW.POPULARJUNK.WORDPRESS.COM

  19. dday02 says:

    Hey Chris,

    I think the real “legacy” that Steinbrenner created is being missed by the common reactions.

    The real enduring legacy that George forwarded was his business acumen and ability to turn the Yankees into a lasting product and financial powerhouse. People scoffed at the very idea of a major TV network being owned, operated, and dedicated (largely) to one sports team. However, the YES Network has proved to be the most successful regional sports network in the country. Obviously, there are small markets where this can’t be a viable option, but without YES, does NESN exist as it does currently? I doubt it.

    When Steinbrenner bought the team (after failing to convince Cleveland to sell) it was worth less than $10 million. Now, on an auction, the Yanks are worth $3 billion PLUS. Turning the Yankees into a global brand and the preeminent sports franchise of the last 30 years was not a given back in the ’70s.

    Yes, George till plenty of crazy things and some of the glowing obituary pieces are a little too nice, but you can’t sleep on the financial clout of the Yankees. Bitch at ticket prices and concessions all you want (and I do, because I can’t afford them), but they are under no directive to lower these prices since they are amongst the highest in ticket sales, and directly own their concessions (I think the Cowboys do as well, little shaky on this though).

    Here’s an interesting related piece for side viewing:


  20. jayallure says:

    very nice post, R.I.P to the “BOSS”

  21. howigit says:

    I agree completely. Sure, Steinbrenner won a lot — he had some great teams. But he was a complete ass, had the 17 year gap in championships, and in the 10 years between 2000 and 2009 spent about 700 million dollars more than any other team and didn’t come up with a championship. In other words? For spending the amount of money he did, he was wildy inefficient.

  22. Tom says:

    I don’t think there are too many owners that can show better results so in my mind he remains the greatest owner. But beyond the titles he built the YES Network, the Stadium and all that comes with the Yankees and that is as much a part of being a great owner as the titles and the droughts. In the end the man was a human like us all first and foremost. That means he made mistakes and as we can see as life moved on and he grew older, he learned from those mistakes. As a leader and a businessman he was outstanding. I get to work with many leaders in my job and liken sometimes to GMS III, but I watch to see how they learn from their mistakes and many do not while George did.

    That is the part of the legacy and why the finish from 1995 on is what it is. The core four STAYED in NY because he made the team win and made sure they stayed as best he could (Andy’s Houston sidebar was family driven but he learned from his mistakes too).
    To me listening to the players and like talk about him they all state his tough side, his rough years but the soft side as well. That’s the part that makes him great.

    in the end the large money, the inefficient use of money and bad contracts, well if you have a billion and you earned a billion you can do what you want with it. And thus George had that right. I think if we all had a billion to spend on a franchise I gather we’d make mistakes too.

    So I respectfully disagree with the post title. and ask you list who was a better Yankee owner or other owner and why. in some regards that will be hard to do since between titles or dollars spent there are not equals but we can wait and see.

  23. dabsportstalk says:

    I like the blog Chris. The title is misleading as others have stated but overall you did well

  24. Rhino Rant says:

    Absolutely wonderful post! I’m glad someone wasn’t afraid to post the negatives of the Steinbrenner era that so many main media outlets were. A 17 year droubt in a 37 year period? Besides, is 7 titles in a 37 year period really that great considering the money pumped into that organization? Plus, Steinbrenner took over a winning team, not a bad team. And he was nowhere near the first to develop a media empire as Ted Turner created a television network for the Braves nearly 30 years before Steinbrenner’s YES network. I totally respect Steinbrenner’s will to win but to call him a visionary or baseball figurehead is asinine. If he makes the hall of fame with two baseball suspensions (and remember, his own advisors had to tell him there were no takers for Bernie Williams) how does Pete Rose not make the hall?

    Great article.


  25. mikekrumrei says:

    Nobody hates the Yankees like I do. But George Steinbrenner, the polarizing figure he was, epitomized the N.Y state of mind. He demanded results and he demanded them now. He was a perfectionist that was not afraid to burn bridges with his staff and the rest of league to bring his team the glory and accolades he demanded of them.

    Was he a saint? Not even close, the Dave Winfield incident that got him banned from the league for two years was a debacle of the highest owner. He served his time, got back behind the desk as started rattling off pennant wins and championship rings.

    Steinbrenner revolutionized the way Major League Baseball owners run their teams. I would love to sit here and spout off about how there is a line of Red Sox fans ready to piss on his grave, but that is not the point.

    Here is the last thing I’ll say, every owner in the league would follow the Yankees model in a heartbeat if they had the money and foresight to do what Steinbrenner did in building the Yankee’s brand and media exposure.

  26. verdun2 says:

    Steinbrenner, to me, is a certain Hall of Famer, but I agree he isn’t the greatest owner in Baseball history. Heck, he’s not even the greatest owner in Yankees history. I give you Colonel Jacob Ruppert who brought Babe Ruth to NY, picked up Lou Gehrig, Bill Dickey, Joe DiMaggio, and Joe Gordon (among others). Top that crew, Georgie.

  27. agent_99 says:


    A link from a link from a link got me to this blog, and I am grateful because I found your article interesting and insightful. Taking in your article and all of the comments made to this point has helped me gain a greater understanding of Steinbrenner and his influence on baseball, New York, and sports in general. I think Steinbrenner’s personality type, while uncommon in the population at large, is very typical among those who achieve any measure of success and/or greatness in life, and is driven by a strong desire for validation, which, in turn, produces results. In Steinbrenner’s case, division titles and championships. But this same personality type comes with its own destructive baggage, which your article nicely articulated.

    Steinbrenner: best owner ever? That is a debate that will continue for as long as sports remain relevant to our society, and this blog has made a valid contribution to that discussion.

  28. Vince V. says:

    Chris, excellent post. What Steinbrenner did for not only baseball, but sport in general, is set a measurement that all others are judged by. Look at what the Miami Heat did in the past few weeks. We forget that baseball is a business. The owners are in it to make money. If there was no profit to be made, half the owners in sports wouldn’t invest in a team. Steinbrenner invested in his team as others here have mentioned.

    Look at the brand that is the New York Yankees. We see people in developing nations wearing Yankee tees and hats. Say what you will about the man as a leader or his meddling on and off the field (Billy Martin anyone?) but he remade the Yankees into a global organization.

    I do agree he wasn’t the most efficient from an investment standpoint, but 7 championships is something to be proud of.

  29. LawLadle says:

    The stability angle is an interesting spin; I wonder if statistical data supports your theory?

  30. dobiemaxwell says:

    Hi Chris,

    Solid post, packed with facts and valid points. Thanks for reading my blog, I am a comedian and touring constantly and don’t always check my comments, etc. If you’d like a copy of my comedy CD, send me a mailing address and I’ll ship one out. THANK YOU for your comments. Keep up the good writing, I enjoyed the post very much.



  31. phoenixinquirer says:

    Greatest Owner? No. But I think you discounted the effect of having too many egos around. Anyone can buy talent, but it does take the right manager to make it coagulate. The Yankees really didn’t reach their current plateau until Joe Torre arrived and kept everyone’s talents in check. The 1977 and 1978 titles were merely getting lucky, even though those teams were swarming arguably with even more talent than their 90’s counterparts.


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