Premium players require premium contracts. The Chicago Cubs have learned that fact the hard way.

Chicago has swung and missed at big-time free agents for many years, usually because other teams are willing to outbid the Cubbies. But, there have been times when the Cubs have landed the big fish. Incredibly, Chicago has never had to spent more than $200 million on a player contract.

At some point that will change, but here are the five largest contracts by total value that the Cubs have signed of all time according to Spotrac. Plus, analysis on whether the deal was worth it.

Charles LeClaire-Imagn Images

Eight years, $184 million, signed in 2016

At the time, Heyward was entering his age 26 season, had been an All-Star and a three-time National League Gold Glove winner as a right fielder. He was well worth the cost. He won two more Gold Gloves with Chicago and was a key piece in the franchise’s World Series title in his first season.

Injuries started to become an issue after that season, and he never won another Gold Glove after 2017. He also never went to the All-Star Game again. In seven seasons with Chicago, he slashed .245/.323/.377 with 62 home runs and 289 RBI. The Cubs released him after the 2022 season and ate the final year of his contract.

Worth it? He batted .230 in the World Series season and played a solid defensive right field when healthy. But he batted better for both Atlanta (.262) and St. Louis (.293) before he arrived, leaving one to believe that the financial outlay wasn’t worth the return.

Dansby Swanson

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Seven years, $177 million, signed in 2023

The former first-round pick was a solid piece of the Atlanta Braves when he broke in during the 2016 seasons. He played seven years for Atlanta before signing with the Cubs. He is the only current player on the list. In his last season with Atlanta, he was an NL Gold Glove shortstop, an All-Star and finished in the Top 20 in MVP voting. He duplicated the feat in his first year in Chicago.

In two-plus seasons with the Cubs he’s slashed .244/.313/.404 with 56 home runs and 203 RBI. He has avoided injury and proven durable in his age 31 season.

Worth it? The jury is still out. But his batting average has remained consistently in the .240s while with the Cubs and he hits close to 20 home runs each season. Within the context of what he’s done to this point, the Cubs might have spent too much.

Mike Dinovo-Imagn Images

Six Years, $155 million, signed in 2015

Another piece of the 2016 World Series team, he had already been to three All-Star Games and finished fourth in American League Cy Young voting twice. He was an All-Star two more times with Chicago and finished second in NL Cy Young voting in 2016, when he went 19-5 with a 2.44 ERA as he pushed the Cubs to a title. In six seasons with Chicago, he was 77-44 with a 3.64 ERA, including 940 strikeouts and 292 walks in 1002.2 innings.

Worth It? He had his best season when it mattered most. He was the NLCS MVP that year and went 1-1 in the World Series. He also won 18 games in 2018. He rarely missed a turn in the rotation. So, yes, worth it.

Alfonso Soriano

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Eight years, $136 million, signed in 2007.

When Soriano arrived, he was entering his age 31 season. He was a five-time All-Star, a four-time Silver Slugger and finished third in AL MVP voting in 2002. He was an All-Star in his first two years in Chicago and finished 12th in NL MVP voting in his debut season. In seven seasons he slashed .264/.317/.495 with 181 home runs and 526 RBI. With more than one year left on his deal he was traded to the Yankees in 2013.

Worth It? He helped the Cubs to two playoff appearances in 2007 and 2008, but he batted under .200 in the NLDS. He had more home runs and RBI with the Cubs than he had with any other club. He had a consistent bat, too. But, in terms of expectations, the Cubs paid too much.

Kamil Krzaczynski-Imagn Images

Six years, $126 million, signed in 2018

Darvish was 31 when he signed with the Cubs. He also didn’t pitch much due to injury. In three seasons, one the COVID-shortened 2020 season, he started just 51 games and went 15-14 with a 3.60 ERA. His eight wins did lead all of baseball in 2020 and led to him finishing second in NL Cy Young voting.

Worth it? The Cubs traded him to the Padres three years into his contract. So, no, the deal wasn’t worth it — unless one considers one of the players the Cubs got in return for Darvish, outfielder Owen Caissie, worth $126 million?

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