Some Insight from Billy Joel

by Paul Semendinger

July 17, 2026

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The legendary Billy Joel was interviewed on Rick Beato's youtube channel recently.

In this interview Billy Joel gave some sage advice for people who might have, at one time, been great at what they did, and might even be still loving what they do, but also not realizing that their time for greatness had come - and gone.

As part of the interview, they discussed Billy Joel moving on from performing at Madison Square Garden and also Joel's decision to stop recording studio albums.

The interview in its entirety is well worth listening to, but I am going to highlight just a few of Billy Joel's observations - ones I feel that relate to the way the Yankees are operated:

When asked why he stopped playing MSG, Billy Joel responded:

"I didn't want it to end, but I thought, I have been here for ten years, it's time to move over. Don't overstay your welcome..."

Later, Rick Beato asked Billy Joel about artists who keep recording past their primes. That exchange basically went like this:

Joel: I decided I wasn't going to do it any more (record albums) because I have heard artists who keep putting out records and they are past...

Beato: Do they dilute their catalogue in that way?

Joel: They dilute their legacy. Maybe they're not as good as they used to be - or they aren't motivated as they were. It ends of trailing off...

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Let's take a look at what Billy Joel stated in relation to one of my favorite musical artists of all-time...

Widely considered one of the greatest song writers of the 20th century, the great Paul McCartney had some solo albums that were tremendous.

For example, Band on the Run has sold over 7 million copies.

McCartney had eight albums in the 1970s that each has sold over one million copies. Today Macca is still recording albums, but they are nowhere near the quality of those first ones - nowhere close. McCartney's best selling album from this century, since 2000, Chaos and Creation in the Backyard (2005), hasn't yet sold even 800,000 copies.

The last time Paul McCartney had a number one single was 1983 - Say Say Say (with Michael Jackson). The last time he had a number one single on his own was 1978 (With A Little Luck).

Thank about that. McCartney has released eight LPs in the 2000s. As far as singles, he released eight after With A Little Luck in the 1970s, about twenty solo singles in the 1980s, fourteen in the 1990s, and more than 25 singles in the 2000s. That's a boat load of songs, all from a master artist, one of the best of all time, and one of the most successful, and yet, since 1978 none reached the top without the contribution of another artist on the same record. (Note - I am no expert on musical releases, my numbers might be a little off, I counted songs as listed in McCartney's discography on Wikipedia. Still, the bigger point remains whether the number is 18, 23, 25, or 29 singles in the 2000s - or whatever decade you look at.)

McCartney is still recognized as a person who wrote great songs, but very few consider him a person who still writes great songs. When one goes to a McCartney concert today, they go to listen to songs from long ago - not the newest songs he has written.

***

In a similar manner, Brian Cashman has served as the General Manager of the Yankees since 1998. He was the Assistant General Manager from 1995 to 1997. In short, Cashman has served as one of the highest (or the highest) ranking member of the Yankees' front office for over 30 years.

At the start of his tenure, Brian Cashman found great success. The Yankees won World Series in 1996, 1998, 1999, and 2000. After about a decade of falling short of the ultimate prize, Cashman's team won the World Series again in 2009. But since then... nothing. No World Championships.

Leaders have a shelf life. There comes a point when they no longer have the skills, the knowledge, the motivation, the insights, or the ability to lead the way they once did. This is, simply, a fact.

This also does not mean that they weren't great. It means that the time when they were great has gone.

It seems clear that this applies to Brian Cashman.

Just as recording artists dilute their legacies with bad songs and albums, Brian Cashman has diluted his legacy from a General Manager who knew how to build championship teams to a General Manager who cannot build an ultimate winner any longer.

Brian Cashman's greatest period was at his start. Those Yankees teams won World Series. He no longer builds teams that win championships. Over the last 26 seasons, he has only delivered one World Championship.

What was once a legacy of greatness has turned into a legacy of building teams that continually fall short.

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