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Long Term Cubs Contract Ranking From Anthony Rizzo to Jason Heyward

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Dansby Swanson on Wednesday officially marked a milestone in Cubs history with the team announcing a seven-year contract second only in franchise history to Jason Heyward in total value and second only to Jon Lester in average annual value.

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Given the risks inherent in any long-term contract,

Ranking of the six previous decades in the club’s five-plus-year history, listed from best to worst:

A +

1B Anthony Rizzo, 7 years old, $41 million (May 2013)

Signed to an extension a year early in the major leagues, Rizzo’s contract included three All-Star selections, four Gold Gloves (including the Platinum Glove), three MVPs (two in the top four), and three MVPs. Series starring and it was so good, in fact, that it became a nine-year, $73 million deal when two options were exercised and the escalators were included.

a

LHP Jon Lester, 6 years, $155 million (Dec 2014)

One of the best long-term gambles for any team, Leicester’s latest signing gave the Cubs an instant credibility rebuild even before Leicester set the tone for six straight winning seasons that included five playoff appearances. He’s earned two All-Star appearances and a Cy Young runner-up finish along the way, averaging 32 starts in MLB’s five full seasons during the decade (and making all 12 scheduled starts during the pandemic-shortened 2020 season).

B

SS Starlin Castro, 7 years old, $60 million (August 2012)

The Cubs didn’t hold strong with the team’s first extension, but they sure got a lower-than-market cost with a homegrown player who was already a two-time All-Star and 2011 league leader when he signed. Castro made another All-Star team as a Cubs and fourth quarterback after the Cubs traded him to the Yankees to free up enough payroll space for 2016 to sign eventual World Series MVP Ben Zobrist.

B-

Alfonso Soriano, 8 years old, $136 million (November 2006)

A serious hamstring injury in his first year of the deal depleted Soriano of the stealing side of the 40-40 player the Cubs paid for. But when he could walk, he would play. He produced 218 home runs and two All-Star appearances (while two playoff appearances out of the gate) before being traded to the Yankees for a payroll dump during the sixth year of the deal. Often overlooked, his work with coach Dave McKay made him an above-average left fielder at the back end of the decade.

c +

RHP Yu Darvish, 6 years old, $126 million (Feb 2018)

A miserable start to a year and a half into the decade—when the Cubs desperately needed his production—prevents this from getting an A. From the All-Star break in 2019 through the pandemic-shortened 2020 season, Darvish has been one of the Cubs’ best pitchers, including That’s second in Cy Young voting for 2020. He’s continued to perform with the Padres since the pay cut deal, earning a 2021 All-Star appearance ahead of an even better 2022 season. If anything, he’s underpaid as he enters the final year of that contract.

d +

RF Jason Hayward, 8 years old, $184 million (Dec 2015)

Hayward was a 26-year-old former All-Star who came off a 6.9 bWAR season when he earned a total value less than at least two other clubs that offered to sign with the Cubs. War’s combined average in seven subsequent seasons was less than 9, and the Cubs released him this winter with a year remaining on the deal. Two Gold Gloves, an uncommon club impact, an explosive 2020 offense during the division title run, and one memorable rain delay speech prevent this from receiving a F grade.

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