The Phillies will conclude their series against the Cubs on Sunday night, but at one time, Philadelphia’s biggest star nearly ended up in the opposite dugout at Wrigley Field.

Bryce Harper is still under contract with the Phillies after signing a 13-year, $330 million agreement in 2019, which features a full no-trade clause and no opt-out provisions.

Although the Cubs were once rumored to be interested in Harper during his free agency, budget limitations and existing roster commitments made a deal unlikely. Cubs owner Tom Ricketts has since admitted he regrets not being more aggressive in trying to sign Harper.

Harper remains a central figure for the Phillies, playing a major role in their recent success, including multiple World Series appearances. He is projected to stay with the team through the 2031 season.

Bryce Harper recently shared that the Cubs were once his top destination.

“Heading into that offseason, they were the No. 1 team on my list,” Harper told Patrick Mooney of The Athletic. “No question about it.”

It’s fascinating to imagine how different things might have been for both franchises. If the Cubs had pursued Harper — a six-time All-Star and the 2015 NL MVP with the Nationals — they might have been able to extend their competitive window.

Following a Wild Card loss to the Rockies in 2018, the Cubs stumbled to 84 wins in 2019, their worst record since 2014. This decline ultimately led to the dismissal of manager Joe Maddon. Team president Theo Epstein departed after 2020, and his successor, Jed Hoyer, eventually traded away cornerstone players from the 2016 championship team — Kris Bryant, Anthony Rizzo, and Javier Báez — during the 2021 trade deadline.

Could Harper’s presence have prevented the Cubs’ downturn during the 2021 and 2022 seasons when they finished under .500? It’s a plausible “what-if” that could have dramatically altered the past six years, during which Chicago hasn’t won a single playoff game. However, Mooney reported the Cubs never pursued Harper.

Part of the hesitation likely stemmed from financial constraints. Chicago already had Jason Heyward under contract for $23 million per season through 2023. Both Heyward and Harper were right fielders at the time, though Harper eventually transitioned to designated hitter duties in 2022–2023 before becoming a full-time first baseman in 2024.

Had the Cubs signed Harper to the same 13-year deal, it could have also impacted the construction of their current roster. Would Hoyer have still traded for MVP contender Kyle Tucker or acquired promising first baseman Michael Busch? Harper’s signing might have forced a very different set of moves.

While we’ll never know exactly how it would have played out, one thing is clear: Bryce Harper wanted to be a Cub, and MLB’s current landscape would likely look very different if that had happened.