5 Worst Cubs Free Agent Signings Ever

You can’t have a 108-year-long championship drought in your franchise’s history without making a lot of mistakes along the way. The Chicago Cubs know all about errors that can set a franchise back from the promised land, signing many players over the years who didn’t live up to expectations.

Out of the many signings that didn’t pan out, there were some lessons that were more expensive to learn than others. Here are our picks for the five worst-ever Cubs free agent signings, costing the team over a quarter-billion dollars in total.

Jason Heyward

When he made his MLB debut, many thought Jason Heyward would be the next big thing. He had become an All-Star in his rookie season, and in his one year with St. Louis, he batted .293 with 13 home runs and had an amazing WAR of 6.9. Heyward then became a free agent prior to the 2016 season, and the Cubs jumped at the opportunity.

Heyward signed an eight-year contract worth $184 million. While his defensive play was solid and he became a good teammate, Heyward, unfortunately, didn’t live up to his bulky contract. Heyward’s final year was bought out by the Cubs, and in seven seasons he batted just .245 with 62 home runs. That’s a good single-season performance, but over seven years is a massive letdown.

Todd Hundley

Todd Hundley was one of the best catchers in Major League Baseball throughout the 1990s, especially toward the later part of the decade when he was with the New York Mets. While in New York, Hundley became a two-time All-star and at his best was hitting .280 in a season. In 2000, Hundley found himself with the Dodgers and had a solid season, hitting .284 with 24 home runs.

The Cubs signed him after the 2000 season, giving him $23.5 million over four years. Many thought that Hundley was the missing piece, but he rubbed fans the wrong way almost immediately after being signed. Hundley lasted just two seasons with that four-year deal, hitting for a .199 batting average and 28 home runs. He then ended his career after the 2003 season, which was spent back with the Dodgers.

Milton Bradley

Milton Bradley had a unique name and personality, entering the league in 2000 with the Montreal Expos. After making stops in Cleveland, Los Angeles, Oakland, and San Diego throughout the 2000s, Bradley found himself in Texas for one season. There, he became an All-Star for the first time thanks to his .321 batting average and .436 on-base percentage.

When he became a free agent, the Cubs gave Bradley a three-year deal worth $30 million. Almost instantly, he became a bad teammate and started talking trash to fans, all while having one of the most memorable blunders in baseball history when he forgot how many outs there were, leading to an opponent scoring. Bradley made it just one season as a Cub, finishing with a .257 batting average and 12 home runs.

LaTroy Hawkins

If you look at his overall statistics, LaTroy Hawkins was not bad, but Cubs fans who watched every game in 2004 and 2005 know why signing him to a big contract was a mistake. Hawkins seemingly came out of nowhere in 2002 and 2003 when he put together two amazing seasons with the Minnesota Twins. The Cubs then signed him to an $11.2 million contract over three seasons.

Hawkins was brought in as a set-up man but became the closer due to an injury to Joe Borowski. Hawkins was traded halfway through his second season, finishing his Cubs career with a 2.76 earned run average. That sounds fine on paper, but many of the runs that Hawkins gave up were in crucial situations which ultimately kept the Cubs from returning to the playoffs in 2004.

Edwin Jackson

Edwin Jackson had 16 different stints with MLB teams during his career which lasted from 2003 until the end of the 2019 season. At one point, he was a can’t-miss prospect who came up with the Dodgers, but ultimately became a journeyman with his Cubs tenure marking the end of his ‘potential.’ The Cubs gave Jackson a four-year, $52 million contract before the 2013 season, and it did not go well at all.

Jackson was traded part-way through his third season to the Atlanta Braves, but not before seemingly setting the franchise back. Jackson had a record of 16-34 with the Cubs and a 5.37 earned run average. Thankfully, his departure marked the beginning of the next step in the Cubs rebuild, leading to a 2016 World Series title.