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Alex Bregman to Cubs and a Bears win. What a night for Chicago sports.

by January 11, 2026
by January 11, 2026

Simply, it was the greatest sports evening in Chicago since 2016.

While the Chicago Bears were making arguably the greatest comeback in franchise history against the Green Bay Packers on Saturday night in the playoffs, the Chicago Cubs were making their biggest free-agent splash in a decade with a five-year, $175 million agreement with infielder Alex Bregman.

“Big night for Chicago,’’ Scott Boras, Bregman’s agent, said in a text to USA TODAY Sports.

So, while the Bears were coming back from a 21-3 halftime deficit to win 31-27, Boras and the Cubs were actually in the middle of negotiations?

“Bears game?’’ Boras texted USA TODAY Sports. “I was packing the green in for Breggy with the Cubs.’’

Oh, did he ever.

The Cubs, who tried to sign Bregman a year ago to a four-year, $115 million deal, got their man and stole him away from the Boston Red Sox with the richest salary in Cubs’ history.

And after listening to critics all winter, saying that they haven’t made enough moves or spent enough money to make themselves World Series contenders − or at least better than the Milwaukee Brewers in the NL Central − they shelled out the big cash after acquiring Miami Marlins starter Edward Cabrera just three days ago.

Just like that, the Cubs have got folks in Chicago believing it could be 2016 all over again, the year they won their first World Series since 1908.

Certainly, Bregman, 31, is a huge winner. He opted out of the $80 million owed to him the next two years by the Boston Red Sox, and spun it into a franchise-record $35-million-a-year deal with a full no-trade clause and no opt-outs. The only Cubs’ contracts bigger in total value is Jason Heyward’s eight-year, $184 million contract and shortstop Dansby Swanson’s seven-year, $177 million contract.

Bregman, who turns 32 in March, will now earn $215 million over six years.

Just like that, the Cubs could be a giant in the NL. They now have a wealth of depth in their infield in which they could either slide Matt Shaw to second base and trade Nico Hoerner or make Shaw a super utility player and keep Hoerner for one more year before he hits free agency.

No matter, the Cubs feel as if they’re set, and love Bregman’s leadership skills, as he has been in the playoffs every full year of his 10-year career.

This is why the Red Sox badly wanted to bring him back and were runner-up in the negotiations. The Arizona Diamondbacks also had interest in Bregman, but once they decided to retain All-Star second baseman Ketel Marte, they dropped out of the Bregman sweepstakes, leaving the Cubs and Red Sox as the two finalists.

Bregman, who hit .273 with an .821 OPS with 18 homers and 28 doubles last season, is the biggest free agent to sign this winter. Considering he’s two years older than Cody Bellinger, it perhaps illustrates why Bellinger has not accepted the Yankees’ five-year offer in excess of $150 million.

Bregman’s signing now leaves the Red Sox badly needing Bo Bichette, who also is being courted by the Philadelphia Phillies and Toronto Blue Jays. Bichette has a zoom call meeting Monday with the Phillies.

The Cubs couldn’t care less what happens next. They believe they’re set now. They’re convinced they can win their first NL Central title in a full season since 2017.

And, hey, with the Cubs’ convention scheduled this upcoming weekend, they not only plan to celebrate the 10-year anniversary of their World Series, but believe it could be a prelude to an October to remember in 2026.

What a night in Chicago, with the Bears winning at Solider Fielder and the Cubs celebrating in their offices at Wrigley Field.

Who would have imagined a brutally cold, blustery evening in Chicago could feel so beautiful?

Follow Nightengale on X: @Bnightengale

This post appeared first on USA TODAY
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