Who is the highest-paid player in Cubs history?

It took the Cubs 108 years to break their World Series curse, but spending was hardly an issue.

Though the Ricketts family has been under the microscope for how the team uses its money, Chicago has routinely had an above-average payroll. Some players have even made nine figures playing for the North Siders.

But which player has gotten the richest from the Cubs? Here are the top five based on money they made while playing for Chicago (per Spotrac):

5. Aramis Ramirez

Ramirez was part of one of the most lopsided trades in MLB history. The Cubs acquired the promising third baseman and outfielder Kenny Lofton from the Pittsburgh Pirates during the 2003 season while surrendering Jose Hernandez, Matt Bruback and Bobby Hill. The deal helped propel the Cubs to the NLCS that season (which we won’t talk about), while the Buccos didn’t finish a season above .500 for another 10 years.

The third baseman hit 36 homers and drove in 103 RBIs during his first full season with the Cubs in 2004 and was quickly rewarded. He signed a four-year, $42 million extension in April of 2005 and worked out a five-year, $75 million deal in 2007. In all, he made over $97 million from the Cubs before joining another NL Central foe, the Milwaukee Brewers, in 2012.

4. Carlos Zambrano

Zambrano was a pitcher who showed his value with both his arm and his bat.

The longtime Cubs starter was named an All-Star three times and also won three Silver Sluggers during his 11 years on the North Side. His 1,542 strikeouts in a Cubs uniform remain second in team history behind Fergie Jenkins’ 2,038, while his 24 home runs are ninth-most all time among players who were only pitchers.

Big Z made over $112 million over that stretch with his biggest payday coming from a lucrative five-year, $91.5 million deal that kicked in during the 2008 season.

3. Sammy Sosa

Sosa was one of the most electric players to ever put on a Cubs uniform.

He arrived in the North Side and 1993 and by 1998, he was blasting home runs at a historic rate. His 1998 season was among the most memorable in baseball history: 66 home runs, 158 RBIs, an All-Star appearance, a Silver Slugger Award, an NL MVP Award and an iconic home run chase with Mark McGwire.

Perhaps money helped propel him to that astonishing season. (What else could it be?) He signed a four-year, $42.5 million deal that started in 1998 and a four-year, $72 deal that began in 2002. He made over $117 million during his time with the organization.

The slugger has failed to make the Baseball Hall of Fame and has been kept out of a return to Wrigley Field since his MLB career ended in 2007. But could a reunion be in order soon?

2. Alfonso Soriano

The Cubs made a big splash with Soriano.

The team gave the outfielder/second baseman an eight-year, $136 million deal back in 2006, and it was looking like a solid signing at first. Soriano was named an All-Star in each of his first two seasons playing at Wrigley Field, but then he became an expensive player on a team that wasn’t going anywhere. He was traded to the Yankees, one of his former teams, in 2013 as the Cubs continued to pay a sizable portion of his salary.

Soriano totaled 181 homers, 526 RBIs and just over $130 million from the Cubs in his nearly seven years with the club.

1. Jon Lester

Lester is the only player on this list who was part of the Cubs’ curse-breaking World Series team, so it’s only right that he’s the top player here.

The Cubs signed the former Boston Red Sox ace to a six-year, $155 million deal in 2015. After an 11-12 first season in Chicago, Lester became an All-Star in 2016. He started Games 1 and 5 of the Fall Classic and pitched three innings of relief in the iconic Game 7 win. Lester pitched in Chicago for those six seasons before joining the Washington Nationals in January of 2021.

Lester made $145,555,556 in all from the Cubs, and it was worth every penny for the World Series title.