Alex Bregman and the top 5 largest Cubs free agent deals of all-time

The Chicago Cubs made a very surprising move by inking All-Star third baseman Alex Bregman to a five-year contract on Saturday.

Bregman's contract is among the largest in team history. The deal, along with a flurry of other moves this offseason, suggests a commitment to consistent playoff contention by Cubs' ownership as the team rarely dishes out contracts of this magnitude. With that being said, here's where Bregman's deal ranks among the largest contracts in Chicago Cubs history.

5. Alfonso Soriano: 8 years, $136 million

Alfonso Soriano came to the Cubs after compiling six impressive major league seasons with the New York Yankees, Texas Rangers, and Washington Nationals. Soriano had already made five All-Star teams and recorded a third-place finish in MVP voting by the time he came to Chicago in 2008.

Soriano continued his All-Star trend in his first two seasons with the Cubs, but his production started to wane as he continued to age past his prime. With the team also enduring a full rebuild, the Cubs traded Soriano with a year-and-a-half left on his contract. Although many consider Soriano's deal to be among the worst in Cubs history, he was statistically an above-average hitter for the majority of his tenure with the team.

4. Jon Lester: 6 years, $155 million

Jon Lester still represents the biggest commitment to a pitcher the Cubs have ever made and it was well worth the money. Lester came in as the Cubs front office was turning the corner on their rebuild and looking to make a deep playoff run. The southpaw already had a long track record of consistency in the majors with eight straight seasons of at least 31 starts under his belt.

Lester continued to stay remarkably healthy after he came to the Cubs, and he became an anchor for the pitching staff alongside Jake Arrieta. In the World Series-winning 2016 campaign, Lester logged arguably the best season of his 16-year career with a 2.44 ERA and 197 strikeouts over 202 2/3 innings pitched, finishing runner-up in National League Cy Young voting.

3. Alex Bregman: 5 years, $175 million

Bregman's deal ranks third on the team's all-time list as the Cubs look to re-establish themselves as a perennial playoff contender. After Matt Shaw's inconsistent rookie showing, Bregman projects as a significant upgrade offensively, while still offering great defense at third base and leadership in the clubhouse. There are risks with Bregman entering his age-32 season at the time of the signing, but he comes to the Cubs as a three-time All-Star and former Gold Glove winner.

This deal marked the first time in years the Cubs were willing to give a player deferred money (reportedly $70 million). Many top free agents have been asking for deferred money in their contracts in recent years, and the Cubs likely wouldn't have been able to land Bregman if they didn't break with ownership's policy on this issue. This suggests Chicago feels very strongly about Bregman as their refusal for contracts with deferred money likely prevented them from signing him last go-round.

2. Dansby Swanson: 7 years, $177 million

Dansby Swanson signed his deal with the Cubs before the 2023 season, and he has been as consistent as you can expect. He plays exceptional defense at shortstop, misses very few games, and routinely bats around .240 with 20+ homers and 75+ RBI. Swanson has also been pivotal for the team with his intangible leadership qualities, which helped transform the Cubs' clubhouse in the era after the World Series core was traded away.

Heading into 2026, there are still four years left on Swanson's deal and he will be 35 years old by the end of it. So far, it has been worth the money in my opinion. He is not a superstar, but he is extremely reliable, experienced, and professional.

1. Jason Heyward: 8 years, $184 million

Perhaps the most controversial contract in Cubs history: Jason Heyward. In terms of production at the plate, Heyward clearly fell well short of his annual $20-ish million paycheck. The lack of clutch-hitting and power was a tough pill to swallow, but he was always consistent on defense and on the basepaths.

And there is a serious possibility that the Cubs do not win the 2016 World Series without Heyward on the roster. In addition to his elite defense in right field for that entire season, Heyward delivered a famous rain delay speech during Game 7 of the World Series. The Cubs subsequently rallied in extra innings to win their first championship in over a century. There were clearly a multitude of other factors involved with that victory, but it makes Heyward's contract sort of worth it in hindsight.