Here's where Alex Bregman ranks among richest contracts in Cubs history

The Chicago Cubs have officially signed Alex Bregman, locking him up to one of the richest contracts in team history.

Bregman, who won two World Series championships with the Houston Astros before playing for the Boston Red Sox during the 2025 season, will hope to inject more offense into the Cubs’ lineup this season, and he will also provide strong defense at third base.

Where does Bregman’s contract rank among the biggest the Cubs have ever given out? Here’s what you need to know.

5 – Alfonso Soriano (8 years, $136 million)

Soriano’s decision to sign with the Cubs prior to the 2007 season kicked off the Lou Piniella era with a bang in Chicago. He helped lead the team to two consecutive National League Central titles and was named to the All-Star Game in each of his first two seasons.

Overall, Soriano had a solid Cubs career, with 181 home runs, 526 RBIs and 70 stolen bases for the North Siders before rejoining the Yankees in 2013.

4 – Jon Lester (6 years, $155 million)

Along with the hiring of manager Joe Maddon, the signing of Lester signaled that the Cubs’ rebuilding effort was at its crescendo prior to the 2015 season.

Lester ultimately won 77 games in 171 career starts for the Cubs, and he was instrumental in the success of the 2016 World Series champions, posting a 19-5 record with a 2.44 ERA. He ultimately finished second in Cy Young voting that season.

3 – Alex Bregman (5 years, $175 million (reported)

Bregman, picked second in the 2015 MLB Draft, is no stranger to winning, having captured two World Series titles with the Houston Astros before signing with the Boston Red Sox prior to the 2025 season.

In 114 games last season, Bregman hit 18 home runs and drove in 62 RBI’s, slashing .273/.360/.462 for Boston.

2 – Dansby Swanson (7 years, $177 million)

Swanson was actually the first pick in the 2015 MLB Draft, and he has brought Gold Glove-caliber defense with him to the Cubs during his three seasons with the team.

Swanson hit 24 home runs and drove in 77 RBI’s last season for the Cubs, helping propel them to their first playoff appearance in five years.

1 – Jason Heyward (8 years, $184 million)

Heyward’s deal, signed before the 2016 season, was the largest in Cubs history, and while the team did win the World Series in his first season, his career with the team was short of expectations.

He did win two Gold Gloves with the Cubs in 2016 and 2017, and had a solid season in 2019 when he hit 21 home runs and drove in 62 RBI’s. Overall in seven seasons Heyward hit 62 home runs, with 289 RBI’s and a slash line of .245/.323/.377 with the Cubs.