The Value of Leadership

November 10, 2025

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Last week, our Editor-in-Chief, Paul Semendinger published the first article in his series looking at how all the Yankees World Series Championship teams were built.

The following was sent to SSTN by a reader (who wishes to be unnamed, but gives permission to share these thoughts on the site):

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I like your articles because you mention both past and present Yankees teams and players. Most baseball talk shows and tv shows, hosts, media people, etc. don't know much baseball history that took place back in the day.

Your recent article about how the Yankees built their dynasty was interesting. I just want to add some comments about this topic: First, the Yankees Dynasty, starting in 1921 was made possible because for the 1915 season, Jacob Rupert and Tillinghast L'Hommedieu Huston became the owners of the Yankees. The Yankees were going nowhere fast for many years with their previous owners. This is one of many examples throughout baseball history that shows what an incredible difference competent ownership makes.

Ruppert's willingness to spend huge amounts of money in the Yankees was all the

 more remarkable because this was during Prohibition and Ruppert's business(income) came from the beer (brewery) business. To invest huge sums of money during economic uncertainty (Prohibition), indicated how much dedication Ruppert had in building a winning team. 

Ruppert sold his personal items, rare books, and other items to pay expenses. Ruppert poured almost all of his team's profits back into the team and organization, by far a much higher percentage than any team in MLB. From a SABR article, "Furthermore, Ruppert was not taking distributions from his franchise; he was reinvesting all the profits. " The article said the Yankees poured in $ 1.6 million+ in profits back into the Yankees, far more than any other team.

Unlike Hal Steinbrenner who has said he really has no interest in baseball, and who inherited the Yankees, Ruppert had a strong passion for baseball as a youngster. He built the Yankees empire, he didn't inherit it like Hal Steinbrenner.

The key thing that often flies under fans' radar is this: While most of fans' focus is in the Yankees spending more money to acquire players, this should not be the first priority of the Yankees. Ruppert built a dynasty because he did things in the correct sequence, First, he hired  Miller Huggins as manager. Huggins' first season as Yankees manager was 1918, Ruppert got the leaders in place as his first priority. Huggins was a great manager, who started the Yankees dynasty, winning 3 world championships and 6 pennants in the 1920s. Huggins would later get a Monument in Yankee Stadium, and be elected to the Hall of Fame.

A big key to the Yankees success was hiring  Ed Barrow who had many titles( Executive/ GM, was perhaps the most influential person in the Yankees organization. He was the architect of the Yankees dynasty from 1920-1945. During that span, the Yankees won an amazing 10 world series and 14 pennants. The Yankees brought over Barrow from the Red Sox. Barrow was Red Sox manager for 3 seasons prior to joining the Yankees. Barrow had just about every job one could have in baseball: team owner, manager, league president, executive, GM).  

Branch Rickey, who had one of the highest baseball I.Q. in history, and one of the most influential people in baseball history, said this about Ed Barrow: " I say there has never been a smarter man than Mr. Barrow. He knows what a club needs to achieve balance, what a club needs to become a pennant winner. I perhaps, can judge the part, but Mr. Barrow can judge the whole." Barrow is honored in Monument Park in Yankee Stadium and has been elected to the Hall of Fame.

In addition to getting Barrow to join the Yankees from the Red Sox, Paul Krichell, a scout for the Red Sox, joined the Yankees for the start of the 1921 season. Barrow convinced Krichell to join the Yankees. Krichell has the credentials to be quite possibly the greatest scout in history. He is credited to have signed or discovered players such as Lou Gehrig, Red Rolfe, Charlie Keller, Vic Raschi, Whitey Ford, Phil Rizzuto, and other significant Yankees players. Krichell made a significant contribution to every pennant winning Yankees team from the early 1920's to the 1960's. 

The key point is that Rupert's huge spending would not have done much unless he had the great infrastructure in place, by getting Huggins, Barrow, Krichell, and others to join the Yankees. Many fans and many in the media talk about how the Yankees bought many of the Red Sox players which was a huge part in creating the Yankees dynasty.  That is true, but the most significant factor in the Yankees creating their dynasty was acquiring the non-players from the Red Sox,( Barrow, Krichell), and manager Huggins from the NL.

Throughout history there seems to be a common trait of all world championship teams. It seems that teams acquire other teams best front office people. In addition to my previous example with the Yankees and Red Sox, there are other examples:

The Cubs broke their curse when they acquired Theo Epstein from Boston to become Cubs' president of baseball operations. The Giants 2010, 2012, 2014 world championships were mostly built on an incredible amount of ex-Yankees who left the Yankees organization and joined the Giants. Brian Sabean( GM), who was influential in the Yankees 1990s-2000s dynasty, along with Dick Tidrow, Director of Player Personnel, assistant to GM for the Giants, Dave Righetti ( who became Giants pitching coach), and more than 10 people, who were once in the Yankees organization, left, seemingly en masse to join the Giants' organization. Most of these scouts, player development personnel, coaches, advisors, etc, were in the Yankees organization when the Yankees were winning world championships and pennants from 1976-1981. The Giants acquired these people and by doing so, they acquired people who had experienced a winning culture from the Yankees. These people brought to the Giants the know-how, what-it-takes experience to bring a world championship team to San Francisco.

When the Astros had great success in winning 2 world championships and 4 pennants since 2017, they accomplished this mainly by acquiring many key front office people from the Cardinals. Only after the Astros acquired the Cardinals top front office people such as Jeff Luhnow, Sig Mejdal, Mike Elias, and others, did Houston start spending the necessary amount of money to build a winner. Luhnow, Mejdal, Elias and others made the Cardinals one of the best, if not most successful teams right before they left to join Houston.

The St. Louis Cardinals were a team going nowhere and had not accomplished much in the 20th century until they acquired Branch Rickey from the St. Louis Browns .

With Rickey as Cardinals GM, the Cardinals became a NL powerhouse as the Cardinals won 6 world championships and 9 pennants from 1926-1946. Even though Rickey was with the Dodgers when the Cardinals won the last few of those pennants, Rickey had brought many of those players to the Cardinals before he left for Brooklyn.

When Rickey left the Cardinals and went to the Dodgers, the Dodgers easily became the most dominant NL team throughout the late 1940s -early 1960s.

The Dodgers current dynasty started to be created when Andrew Friedman became president of baseball operations from the Dodgers in 2015, Since then, the Dodgers have won 3 world championships and 5 pennants, and win their division almost every season. The Dodgers organization, now the best in MLB, became the best franchise soon after Friedman left the Tampa Rays to go to the Dodgers.

Every world series winning team became champions by getting other excellent front office people, scouts, managers, player development people, coaches, etc. to leave their teams to join their new team. The new team then became champions.

Steinbrenner and Cashman don't ever seem as though they will leave the Yankees. So what can the Yankees do to finally win a title besides spend more money?

Here's my suggestion: First, coaches constantly switch teams, they go from team to team. One pitching coach, Carl Willis, of Cleveland, has been one of the most successful pitching coaches in MLB, one of the best in history. He has produced about as many CY Young Award winners as anyone, and despite a low payroll, Cleveland more times than not, seem to have one of the best team e.r.a. in the league. This is even more impressive when Cleveland usually doesn't sign big name pitchers, they instead develop them. Willis has coached a number of MLB  teams before. 

Did the Yankees ever seriously inquire about Willis' availability, and if he is willing to leave Cleveland?  Ex-Yankee, Chili Davis, produced excellent results, in his MLB batting coaching career. The Yankees, I believe, would benefit greatly from his coaching. His approach of hitting to all fields, not always trying for homers, would be a nice change in philosophy, He was a switch hitter, so he can teach all hitters. He played on several world championship teams,  and therefore brings along a winning culture. He had an excellent playing career. Is he even interested in coaching at this point? If he is, the Yankees should have shown interest in him.

Hal Steinbrenner will never fire Cashman, no matter how many years the Yankees go without winning a world series. This would be an acknowledgement that Cashman has failed, and Steinbrenner and Cashman will never tell fans and the media that Cashman has not done a good enough job. However, there is an easy solution to this. 

Steinbrenner doesn't want to fire Cashman, that is obvious. However, instead of firing Cashman, all the Yankees have to do is " promote" Cashman, give him  title such as " President of Baseball Operations" and then hire a competent GM to fill the GM role. This way, the Yankees don't publicly acknowledge what most Yankee fans already know, that Cashman is far from the best GM. A new GM could hire a new manager. This would be addition by subtraction, getting rid of both Cashman and Boone. 

"Promoting" Cashman opens up a world of possibilities. Does assistant GM Brian Sabean, a proven winner and someone, I believe, who should eventually get elected to the Hall of Fame, take over as GM? Would Theo Epstein be interested in being Yankees GM? The Yankees would have so many more possibilities available to them if they " promote" Cashman.