Dansby Swanson on Wednesday officially assumed a prominent place in Cubs history with the team announcement of 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.
Given the inherent risk with any long-term contract,
Grading the six previous contracts in club history longer than five years, listed from best to worst:
A+
1B Anthony Rizzo, 7 years, $41 million (May 2013)
Signed to an extension before he had a full year in the big leagues, Rizzo’s contract included three All-Star selections, four Gold Gloves (including a Platinum Glove), three top-10 MVP finishes (two in the top 4), a World Series championship and was so good, in fact, that it became a nine-year, $73 million bargain when two options were exercised and escalators were included.
A
MLB
LHP Jon Lester, 6 years, $155 million (December 2014)
One of the best long-term pitching gambles for any team, the Lester signing gave the Cubs’ last rebuild instant credibility even before Lester set the tone for six consecutive winning seasons that included five playoff appearances. He 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 contract (and made all 12 scheduled starts during the 2020 pandemic-shortened season).
B
SS Starlin Castro, 7 years, $60 million (August 2012)
The Cubs didn’t get staying power with the team’s first extension of the Theo Epstein regime, but they got below-market cost certainty with a homegrown player who already was a two-time All-Star and 2011 league hits leader when he signed. Castro made another All-Star team as a Cub and a fourth after the Cubs traded him to the Yankees to free up enough 2016 payroll space to sign eventual World Series MVP Ben Zobrist.
B-
OF Alfonso Soriano, 8 years, $136 million (November 2006)
A serious hamstring injury in his first year of the deal sapped Soriano of the steals side of the 40-40 player the Cubs paid for. But when he could walk, he played. And he produced 218 home runs and two All-Star appearances (during a pair of playoff appearances out of the gate) before he was traded to the Yankees in a salary dump during the sixth year of the deal. Often overlooked, his work with coach Dave McKay made him an above-average left fielder on the back end of the contract.
C+
RHP Yu Darvish, 6 years, $126 million (February 2018)
A miserable year-and-a-half start to the contract — when the Cubs needed his production most — prevents this from getting a A grade. From the All-Star break in 2019 through the pandemic-shortened 2020 season, Darvish was one of baseball’s best pitchers for the Cubs, including a 2020 runner-up finish in Cy Young voting. He has continued to perform for the Padres since a payroll-slashing trade, earning a 2021 All-Star appearance before an even better 2022 season. If anything, he’s underpaid as he enters the final year of that contract.
D+
RF Jason Heyward, 8 years, $184 million (December 2015)
Heyward was a 26-year-old former All-Star coming off a 6.9-bWAR season when he took less total value than at least two other clubs offered to sign with the Cubs. His combined bWAR in seven subsequent seasons was less than 9, and the Cubs released him this winter with a year left on the deal. Two Gold Gloves, an uncommon clubhouse impact, a 2020 offensive burst during a division title run and one memorable rain-delay speech keep this from getting a failing grade.