Anthony Rizzo still gets that feeling when he thinks about walking into Petco Park for the first time. A 21-year-old rookie with a lot to prove and everything about the experience felt huge. The Padres’ uniform was more than a jersey. It was his ticket to the major leagues. But the excitement of it all didn’t last long. Those endless flights and the hollow feeling of being far from home all started to take a toll on him. He’d look at the clock. Think, ‘It’s already 1 back home.’ It was a harsh reminder that he was really on his own out there. For a kid who’d grown up on the East Coast, San Diego might as well have been another planet.

It wasn’t just the lifestyle. On the field, Rizzo’s bat went cold. Fastballs over 90 mph ate him alive. The California sun wasn’t living up to its reputation. It felt like he was barely keeping his head above water. “I got called up in San Diego and I sucked,” he said recently. For the first time in his life, baseball felt like a grind he wasn’t winning.

“I’m an East Coast-biased guy. I don’t love the West Coast,” Rizzo admitted on the Glory Daze podcast. “I mean, I do now as I got older, but when I was in San Diego, I was like, I’m three hours away from home, I’m done with the game. I can’t call home, it’s one o’clock in the morning.”

That’s why the call from Theo Epstein to bring him to Chicago was more than a trade; it was a lifeline. In Wrigleyville, Rizzo didn’t just find his swing again; he found a purpose. He challenged the Cubs’ “this is how we’ve always done it” mantra, pushed for a winning mindset, and became the cornerstone of a core that ended a 108-year championship drought. For nearly a decade, he embodied Chicago baseball. His number was on kids’ jerseys, his name was in chants, and his smile was plastered across the city.

And then came 2021. The Cubs, facing a roster teardown, shipped their heart-and-soul first baseman to the Yankees. For some, it was a gut punch. For Rizzo, it became a career-defining pivot. “Getting traded was the best thing to ever happen,” he said. “I love my time in Chicago, but I really grew into a man in New York.”

That’s where the Cubs snub lives. Not in bitterness, but in contrast. Chicago was history, family, and triumph. New York is a place where you’ve got to earn your stripes and prove yourself every day. Rizzo appreciates walking into a clubhouse with stars like Aaron Judge, DJ LeMahieu, and Gerrit Cole. He knew his past achievements meant little now until he earned them again.

“The expectation there to win every day is the best feeling in the world… Those pinstripes definitely weigh a lot heavier than any other uniform,” Rizzo said. And in saying that, he drew a line between the two cities. The one that turned him into a champion and the one that taught him to be tough.

For Cubs fans, it’s a reminder that Anthony Rizzo’s most developmental baseball years may have been in Chicago, but in New York, where his passion for the game really comes alive. And for Rizzo, there’s no walking that back.

Anthony Rizzo from trade bait to Bronx savior?

For Cubs fans, watching Anthony Rizzo get shipped out of Chicago felt like more than a roster move; it felt like a breakup. Here was the guy who carried a .272/.372/.489 slash line, launched 242 homers, and stood at the heart of the 2016 curse-breaking championship. By mid-2021, though, the numbers weren’t as kind. His OPS dipped under .700, strikeouts piled up, and suddenly, the face of the franchise was treated like a piece that no longer fit. One moment, he was a city’s MVP-caliber anchor; the next, he was on the trade block.

The Yankees didn’t see damaged goods; they saw opportunity. And Rizzo wasted no time proving them right. In his first six games in pinstripes, he drove in at least one run every night, something no player in Yankee history had ever done. By the end of 2021, he was hitting 249 with a.340 on-base percentage and.428 slugging percentage. Let’s not forget the 8 home runs and 21 RBIs he managed in 49 games. That’s not filling a gap, that’s stepping in and grabbing the lineup by the collar. In a clubhouse full of sluggers, Rizzo quickly became the steady heartbeat.

And his value only grew with time. In the 2024 ALCS Game 4, after two rough defensive days, Rizzo walked up in the ninth against Guardians closer Emmanuel Clase, the kind of high-90s heat that once haunted him as a rookie, and a go-ahead single that flipped the series momentum. That’s not just redemption, that’s leadership in real time. Around younger Yankees like Oswaldo Cabrera, Rizzo wasn’t just a teammate; he was a mentor. He once compared Anthony Rizzo to Mr. Miyagi. You know the wise coach from Karate Kid. When things got tense, Rizzo was always calm. In a city where pinstripes can crush you, Rizzo’s presence has kept the Yankees standing tall.