The 36-year-old’s 14-year career started as a Boston Red Sox prospect, then he briefly struggled with the San Diego Padres, and finally became the heart and soul of the Chicago Cubs. Though the ending with the New York Yankees in his final seasons wasn’t a fairytale, Anthony Rizzo was all prepared. The former and legendary first baseman is now tackling a very different kind of lineup at home.

During his final playoff run, where the Yankees lost the 2024 World Series to the Los Angeles Dodgers, Rizzo struggled in that Fall Classic, getting just two hits in 16 at-bats. “Enjoy this ride,” Rizzo said, then to his wife and family. “I don’t know how much longer I have to give to the game.”

The first baseman did not find the perfect team for the 2025 season, but a much bigger life event changed his perspective. His wife, Emily, gave birth to their very first child in late June. “That made it so much easier,” Rizzo said. “I gave everything I had on the field and off the field. So when the right opportunities didn’t arise, and we had the baby, just getting to spend so much more time at home and have this summer off, it’s been amazing, and it just all came naturally.”

And the Cubs legend recently shared an update on his new life via an Instagram story. The adorable picture showed his child, a diaper pack sitting right next to a coffee can, with a perfect caption that read: “Sunday morning hit a little different now, Diaper and coffee run.”

Many forget that Rizzo started with the Boston Red Sox when the team drafted him out of high school back in 2007. He spent a few years developing in their minor league system and was then traded to the Padres as part of the deal for Adrián González. Rizzo debuted in the majors with the Friars in 2011. But the first taste of the big leagues did not go as planned. The young first baseman struggled in 49 games and 153 plate appearances, where he managed just a .141 batting average and struck out 30.1% of the time.

So, the Padres acquired Yonder Alonso from the Reds to take over first base and sent Rizzo and Zach Cates to Chicago for pitcher Andrew Cashner.

This trade started a new era for the Cubs

Rizzo blossomed on the North Side. Over his 10 seasons with the Cubs, he batted .272/.372/.489 with 242 home runs and earned three All-Star nods, won four Gold Gloves, won a Silver Slugger, and earned MVP votes in five consecutive seasons that featured two consecutive fourth-place finishes in 2015 and 2016 when he posted a combined .285/.386/.528 slashline and belted more than 30 home runs.

His biggest accomplishment was helping the Cubs win their first World Series in 108 years. Rizzo struggled in the 2016 NLDS but then dominated in both the NLCS and the World Series, where he hit .320 in the NLCS against the Dodgers and .360 against Cleveland in that Fall Classic with three homers and five doubles and an OPS over  1.000.

All good things must end, and it happened with Rizzo as well. The Cubs began rebuilding in 2021 and traded Rizzo, Bryant, and Baez as a part of that. Rizzo landed with the New York Yankees and hit 32 home runs in his first full season (2022) before having an average 2023 season and a struggling 2024 season when the Yankees played the World Series.

Following that World Series, the Yankees declined his $17 million club option for the 2025 season, which made Rizzo a free agent. The 36-year-old waited for a good opportunity that never came. Instead, Cubs chairman Tom Ricketts invited Rizzo and his wife to dinner, where Ricketts personally asked Rizzo if he would officially retire as a Cub. He also offered him a role of club ambassador alongside Andre Dawson, Ryan Dempster, Fergie Jenkins, Lee Smith, Billy Williams, Kerry Wood, and Ben Zobrist.

Rizzo, who was “pretty much done,” happily accepted the offer and celebrated his retirement, throwing a ceremonial first pitch to one of his former teammates, Ian Happ, before joining the fans in left field, where he nearly caught in Moises Ballesteros’ first career homer for Chicago. “There’s no more stress,” Rizzo said. “I just get to enjoy a baseball game. I’ll have a hot dog, I’m gonna have a beer and I’m gonna really just take it all in.”

He will finally get to take it all in. A perfect ending for a true Chicago legend. What is your favorite Anthony Rizzo moment from his amazing career? Let us know in the comments!