The Yankees and Cubs aren’t natural enemies. They don’t have the century-old grudges, the bench-clearing history, or the annual showdowns that define Yankees–Red Sox or Cubs–Cardinals. Their paths cross only a handful of times in a season. And for the most part, their stories unfold in separate corners of baseball’s grand stage. But sometimes, it’s not the schedule or the standings that bring two franchises into the same conversation; rather, it’s a player.
A name with enough history, loyalty, and star power to spark debate between fan bases who usually don’t give each other much thought.
Anthony Rizzo is one of those names. For nine seasons, he was the beating heart of the Cubs. He was the leader in the clubhouse, a cornerstone on the field, and a hero in the city that saw him help deliver a long-awaited World Series title. But baseball careers have chapters, and Rizzo’s latest one has been written in pinstripes.
Now, even as his presence on the MLB stage has quieted, Rizzo can still set off ripples through the sport, especially when his words hint at a perspective that might rub some the wrong way back in Chicago.
“I think for me, professionally and just the person getting traded was the best thing to ever happen. I love my time in Chicago, but I really grew into a man in New York,” Rizzo said in a candid chat with Johnny Manziel on the Glozy Daze podcast. “Chicago is like, almost a little bit of complacency… Then you get somewhere else and you have to earn those stripes again.”
Rizzo on his time with the Yankees#NYY #RepBX pic.twitter.com/h6O55vntBL
— Captain’s Corner (@Captain2Corner) August 8, 2025
Well, Rizzo came to the Bronx at the 2021 trade deadline. And ever since, he, along with Aaron Judge and other Yankees’ stars, has built a tight bond both on and off the field. They’ve shared dinners on the road, leaned on each other in the clubhouse, and stood up for one another under the bright New York spotlight. So, being a veteran of both the Cubs and Yankees, Rizzo’s voice carries real weight. “It was fun earning it, like that respect again. You are going to a clubhouse with Giancarlo Stanton, Aaron Judge, DJ LeMahieu, Gerrit Cole, all these superstars. You wanna show them why I was who I was,” the 36-year-old explained.
He’s a 3x All-Star and a 2016 World Series champ with the Cubs who’s played alongside some of the game’s biggest stars in the Yankees. And for Rizzo, those experiences shaped him into the player he is today. “108 years, you don’t really win anything, you’re not expected to win anything, and then you come to the Yankees, which is a team that expects to win it every single year,” the co-host stated.
“The expectation there(Yankees) to win every day is the best feeling in the world. That’s what you want… I think as I was older, I was in a perfect spot to be there and just always keep everything in perspective and really try to keep it as loose as possible because those pinstripes definitely weigh a lot heavier than any other uniform,” the 36-year-old admitted.
For decades, the Cubs’ culture revolved around resilience and hope in the face of a long championship drought. Fans valued loyalty and perseverance, and there was a romantic, almost underdog feel to chasing wins. However, the Yankees, on the other hand, operate under a culture rooted in tradition, legacy, and constant pressure to win it all. Anything short of a championship is considered a failure. That’s the challenge Rizzo cherished during his time with the Yankees.
So, Rizzo admitting the Yankees being the best thing that happened to him reflects his rigor and determination to face harder challenges!
The Yankees’ winning culture is a pioneer
“The thing that impresses me the most is how the Yankees present themselves. The culture that they have. It’s a presence unlike anybody else. It must be the pinstripes.” Pedro Martinez shared his thoughts about the Yankees’ much-talked winning culture.
So, while some teams celebrate breaking through for a single championship, the Yankees operate with a dynasty mindset. For them, winning once isn’t enough—the job is never done until another banner is raised in Yankee Stadium. And that philosophy has made them more than just participants in baseball history.
Well, the Yankees’ track record of 27 World Series titles isn’t just a statistic. It’s a blueprint for sustained greatness, proving that a culture built on tradition, discipline, and high expectations can stand the test of time.
“You take pride in being a Yankee. You know, when you come here, the No. 1 ultimate goal is winning a championship.” CC Sabathia once said about the Yankees’ winning culture, the same emotion shared by Rizzo.
For more than a century, the Yankees have built their identity on tradition, dominance, and an uncompromising expectation of success. In the Bronx, championships aren’t a lofty dream; they’re the baseline requirement. That relentless standard has shaped a culture where every player knows they are part of something bigger, where the pressure is constant but so is the drive to achieve.
However, the Yankees’ current third-fiddle act in the AL East might not be related to what they stand for. But fans still bet on their winning culture for a turnaround. The organization, being in the business for over a decade, surely knows the best!
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