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Hour 2: Ian O'Connor artwork

Hour 2: Ian O'Connor

The Michael Kay Show

October 13, 2026

Columnist for The Athletic, Ian O'Connor says that while Aaron Boone is a very good manager, it is time for the Yankees to bring in a new voice. Do the Yankees need to spend at all costs?

Speakers Michael Kay, Ian O'Connor, Eric, Cody, Fred, Steve

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2.02 in our two hour extravaganza. Michael Kay with you until 3 o'clock at that time, Don Haun and Rosenberg. Ian O'Connor over the last couple of weeks has written some columns that I wanted him on every single day.

But I said, let's wait till a couple of these columns coalesce and I'll get him on that one day. And today's that day. And you could read Ian in The Athletic, in my opinion, one of the finest columnists in the entire country. And he joins us now. Ian, how you doing?

Ian O'Connor (1:09)

Hey Michael, what's going on? How are you?

Michael Kay (1:11)

Not too much.

Obviously a topic of conversation here, Ian, a lot. Yankee fans, most of them want Boone gone. I was surprised after they got eliminated that you wrote a column that you thought it was time for him to go. Tell me why.

Ian O'Connor (1:26)

Well, listen, I think Aaron Boone is a good manager, sometimes very good. He hasn't been great with the Yankees, and I think at some point after nine years, you need great. And Aaron Judge is going to be 35 in April. And I just think it's time, in some ways, Aaron Boone has the perfect temperament for New York, much like Joe Torre did. But for some reason in the postseason every year, there are breakdowns with this team that sometimes are befuddling. And when you go 0-9 in the postseason for the Yankees, I think it's time for somebody else to take a shot at it, particularly as you're one of the greatest players in Yankees history. His prime is winding down. I know he's gone to bat for Boone, but I just wouldn't listen to a player at this point. I think that it makes sense when you look at other teams in New York that have made changes that at the time were a little suspect, particularly obviously with Jibbido and Mike Brown recently, they sometimes work out.

It's hard to ascertain why. Sometimes you just need a different touch, a different approach, a different style, and a different voice, and suddenly that can get a team over the top. It didn't make any sense really for the Knicks to fire Tibbs and bring in a guy who had never won a championship and been fired four times, much like Joe Tory was fired three times. And that didn't really make any sense either back in 1995

But it worked out, and I'm not saying it works out in every instance because it doesn't, but as much as I think Aaron Boone is a good to very good manager, he is a great representative of your brand with the dignity and grace that he carries himself with. I certainly wouldn't be the one to have to tell him that he's gone because I do think he's done a good job, and I do think he'll go somewhere else and win a lot of baseball games, but I also think it's time for a new voice to take a crack at this in the postseason with the Yankees. I don't think they'll do it. I think he'll get one more year, and then I think if he doesn't win it next year, they'll move on.

Michael Kay (3:29)

All right, so along that line of thinking, how do you then reconcile that Brian Cashman keeps his job after 17 years of no championship?

Ian O'Connor (3:39)

Well, for decades, Brian has, I think, put together a roster that is good enough to make the playoffs with, and I think in the playoffs, I don't think over the last few years, the Yankees have suffered from a talent deficit.

Look at last year, for instance, at the trade deadline, Cashman added all the things that look like that team needed, speed, athleticism, infield defense, bullpen help, and they still didn't win. It seemed to me at that point that there wasn't an excuse for the Yankees not to get back to the World Series. And frankly, after they embarrassed themselves against the Dodgers in the World Series, I thought that was rock bottom. I was pretty convinced they were going to come back in 25 and win the whole thing because the Dodgers not only beat them in five, but embarrassed them on the field, and also in the way they mock them publicly afterward, I thought that was rock bottom, and they'd come back and win it. They not only didn't win it, they didn't win their division, and they didn't win the division series, losing in four. They come back this year, don't win the division series again, losing it to a different opponent, and then get swept in three games. And yeah, I just think that despite what I said about Boone and the way I do appreciate his abilities as a manager and the way he carries himself, I think it's time for a change.

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