Bryce Harper in Chicago is widely seen as the one that got away. Owner Tom Ricketts said in an interview with CNBC that the Cubs “spent a lot of time thinking about what Harper’s worth as a free agent.” The Cubs never initiated anything serious, and Harper ended up signing with the Phillies for 13 years and $330 million.

They are still kicking themselves for not seriously pursuing Harper. And if free agency went exactly as Harper planned, at least early on, he would have signed with the Cubs.

In an interview with The Athletic‘s Patrick Mooney over the weekend, Harper said that the Cubs were “without a doubt” the No. 1 team on his list. Chicago was three years removed from breaking their 108-year World Series drought. Their core players, Anthony Rizzo, Javier Baez and Harper’s childhood friend Kris Bryant, were all getting closer to free agency. It seemed liked the right time for the Cubs to make a big splash, but ownership thought otherwise. The team across town, the Chicago White Sox, actually got more involved in Harper’s free agency than the Cubs.

“It was definitely something that I talked about — wanting to play in Wrigley, wanting to play in Chicago,” Harper said. “One of the better meetings I had was with the White Sox on the other side (of the city). It just didn’t pan out that way.”

Harper has talked in the past about having to warm up to the idea of signing with the Phillies. He had spent his entire career playing against them in the National League East. They had not made the playoffs since 2011. Harper enjoyed being the villain in Philly.

“Philly came in. I’ll tell you, they came in and I wasn’t very excited,” Harper told Barstool Sports in 2020. “I was kind of like ‘I played against you guys,’ and I told them this flat out: ‘We kicked your ass for the past couple years.’ I flat out said that to them.”

But the Phillies ended up being the team that made the winning offer, and it has worked out for Harper. Managing partner John Middleton has largely kept his promise of spending to build around Harper. Harper has also reached the World Series and made three playoff appearances with Philadelphia. The Cubs have not won a postseason game since Harper signed with the Phillies.

“But it’s one of those things,” Harper said. “Looking back on it, it could have been really good, or it could have been really bad, right? You never know. I never fault any organization for not getting a player or not going after a player.”

It’s an interesting conversation considering the context of the Cubs’ season. They paid a steep price to land superstar outfielder Kyle Tucker via trade for a year, and the team’s track record with free agents leads many to believe that they won’t retain him after this season. Tucker could cost over $500 million. Jayson Heyward’s eight-year, $184 million signed before the 2016 season still stands as the largest guarantee the Cubs have ever handed out.

Since Harper’s arrival, the Phillies have handed out seven contracts worth at least $100 million.

“Obviously, I’m extremely happy with where I am in Philadelphia,” Harper said. “I would never change it for the world. I love the fan base, city, everything. It’s a blast. But pre-2019, going into free agency, the Cubs were at the top of my list.”