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Before the MLB lockout, the Chicago Cubs looked like they were in perhaps the strongest position to sign megastar free-agent shortstop Carlos Correa to a long-term contract. But when free-agent negotiations resumed after MLB and MLBPA agreed to end the lockout, the North Siders never made a big pitch, and Correa ultimately shocked the baseball community by signing with the Minnesota Twins.

What happened?

For starters, the Cubs moved fairly quickly to sign veteran shortstop Andrelton Simmons, then signed Japanese outfielder Seiya Suzuki. But they may have done that in part because of movement in Correa’s camp. The team reportedly submitted a lucrative offer to the 27-year-old. However, Correa changed agencies and hired Scott Boras in the middle of January.

That changed everything. Chicago’s initial offer apparently never made its way to Correa, and the Cubs missed out on the prize of the 2021-22 MLB free-agent class.

Carlos Correa seemed like an ideal fit for the Cubs’ retool

After a six-plus year run that saw them break a historic World Series drought but never quite birthed the dynasty some expected, the Cubs entered a transitory phase at the 2021 MLB Trade Deadline.

Chicago traded all of Anthony Rizzo, Javier Baez, and Kris Bryant, cutting ties with three of the most eminent faces of the franchise and preparing to start anew. But while the Cubs floundered from July to October, they came into the offseason with deep pockets and a loaded farm system.

Given that president of baseball operations Jed Hoyer refused to say the word “rebuild” and the space on Chicago’s payroll, the North Siders had every reason to pursue Correa.

At 27, the former Houston Astros star had only just entered the start of his prime. Correa is a five-tool shortstop with tremendous defensive instincts, a cannon for an arm, and quite a bit of pop at the dish. He hit .279 with 26 homers and a 131 OPS+ in 2021, also winning the Gold Glove at shortstop and ranking 12th in Baseball Savant‘s outs above average (OAA) metric.

The Cubs needed a guy they could say they were building around — respect to Willson Contreras, but a catcher is rarely the franchise cornerstone — and Correa could have been that individual. Indeed, Chicago reportedly had a legitimate interest in Correa.

Even after the lockout ended, the Cubs had the inside track. Or so it seemed.

Chicago reportedly offered Correa a big deal, but it never reached him after his agent swap

Although the Cubs signed Andrelton Simmons shortly after the lockout ended, they still had ample room to offer Carlos Correa a sizable contract. However, the North Siders made very little noise in his market.

What’s with all the crickets? Did the front office suddenly lose all interest? Well, not exactly. In actuality, the Cubs might have gotten unlucky.

Stephen Nelson of MLB Network spoke about Chicago’s pursuit of Correa on Wednesday afternoon during an appearance on 670 The Score. He said “representation issues” reportedly got in the way of a deal, then added more clarification on Twitter.

According to Nelson, the Cubs offered Correa a seven-year deal well north of $210 million. However, because of the “complicated nature of Correa’s agent switch,” the two-time All-Star never even saw the deal.

Wow. That’s pretty strange. It’s unknown when the Cubs reportedly made said offer. But the fact that Correa changed agents in the middle of the lockout complicates matters. Teams could not communicate with players during that period.

Would Correa be a Cub had he not sought different representation? If nothing else, it’s worth wondering. The report could also cause more Scott Boras angst from the fans in Chicago.

Scott Boras did well for his client, though North Siders won’t be pleased

Minnesota Twins shortstop and Chicago Cubs free-agent target Carlos Correa runs the bases after hitting a home run during MLB Spring Training in April 2022
Carlos Correa runs after hitting a home run during a Spring Training game against the Boston Red Sox on April 05, 2022 | Brace Hemmelgarn/Minnesota Twins/Getty Images

Truthfully, Carlos Correa’s Twins contract suggests he made the right decision to hire Scott Boras.

Minnesota will pay Correa $35.1 million in annual average value (AAV) over the course of three years. Moreover, Correa has opt-outs ahead of both the second and third seasons of the contract while also possessing a no-trade clause. He has incredible individual leverage and flexibility, and now joins a loaded lineup that could power the Twins near the top of the American League Central division.

Still, there’s no love lost between Boras and Cubs fans, particularly if this report proves true.

Tensions have run high between the Cubs and the game’s top agent in recent years. Boras (rightly) called foul when the Cubs kept Bryant in the minors at the start of the 2015 campaign so as to accrue more service time. In 2020, Boras (h/t Chicago Tribune) singled out the Ricketts family and used the Cubs organization as a reason why players should hold firm on their salaries ahead of the pandemic-shortened season.

In short, there’s always been an underlying strain whenever the North Siders and Boras Corp. do business. He might just have prevented Correa from suiting up at Wrigley Field.