Five Best Chicago Cubs Offseason Acquisitions in the Last 20 Years

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The Chicago Cubs are hesitant to make a splash in the free agency market this offseason. It doesn’t look like that will change anytime soon. So, it’s only fitting that we look back on some of their best offseason acquisitions in the last 20 years. These five players were vital additions to rosters that outperformed their expectations, and some even catapulted the Cubs into contention. Whether they were acquired via trade, or signed as a free agent, all of them have made their mark in the team’s history books.

Cubs Best Offseason Acquisitions in the Last 20 Years

5. Low Risk, High Reward for Dempster

Date: January 21st, 2004

Cubs sign Ryan Dempster to a 1 year/$500,000 contract.

Dempster just went through Tommy John surgery and landed with the Cubs in 2004. He didn’t play until August, but instantly produced in the bullpen. He quickly became one of the team’s best relievers, and eventually would be named the closer. It didn’t stop there, however, Dempster actually made his way into the starting rotation. He became a mainstay for most of the eight-and-a-half-years that he spent in Chicago.

When the Cubs won the NL Central in 2008, Dempster made the All-Star team and was in the running for a Cy Young award. That year he started 33 games, and had a record of 17-6 with a 2.96 ERA. Although past that season, his overall statistics with Chicago don’t jump off the page, he will always be held in high regard by Chicago. Which is probably why he has worked within the organization after his retirement, and lately has been featured on their television network. Another fun fact, the Cubs traded Dempster to the Texas Rangers for a young Kyle Hendricks during the 2012 season. Hendricks is now the team’s ace.

4. A Welcome Gift from the Marlins

Date: November 25th, 2003

Florida Marlins acquire: Hee-Seop Choi and Mike Nannini

Chicago Cubs acquire: Derrek Lee

The now Miami Marlins organization was looking to dump Derrek Lee’s salary, and Chicago was more than willing to take him. Lee ended up being one of the most underrated Cubs ever. He spent six and a half seasons with the team, and had some of the best seasons of his long career.

Lee was incredible in the 2005 season. He had 199 hits, which was first in the NL. He also led the league in batting average, slugging percentage, extra base hits, and runs created. The Cubs’ first-baseman won a silver slugger and the gold glove awards, whilst finished third in the MVP voting. Lee made the All-Star game twice with the Cubs, and was a bright spot, for a team that struggled to compete for a playoff spot. Overall, Lee sported a slash line of .298/.378/.524 with the franchise. It’s unfortunate that they couldn’t find more success during his prime because he gave Chicago his best years. Eventually, he was traded in 2010 to the Atlanta Braves. He played one more season before retiring.

3. The Ultimate Utility Player

Date: December 8th, 2015

Cubs sign Ben Zobrist to a four-year $56 million contract.

Ben Zobrist followed his manager Joe Maddon from the Tampa Bay Rays to Chicago, and can be linked to much of the team’s success. The front office was all-in on Zobrist, which was made clear when they traded their star infielder Starlin Castro to the New York Yankees. Zobrist was mainly featured at second base, but he was truly a jack of all trades. Maddon was able to place him at several different positions on the field, which made their lineup extremely flexible.

In four years with the Cubs, he batted .269/.362/.411. He gave them consistency at the plate along with a focus on contact hitting. His importance was on full display in the World Series. He had 10 hits in the series, none more important than his go-ahead double in the 10th inning of Game 7. He was named the 2016 WS MVP, and will be forever remembered as a Cubs legend for that performance alone.

2. Lester Makes Chicago Instant Contenders

Date: December 10th, 2014

Cubs sign Jon Lester to a six-year/$155 million contract.

In what may be the biggest offseason signing in franchise history, the Chicago Cubs brought in Jon Lester on a massive deal. The future was bright for the Cubs, but this move was what really put them over the top. They surpassed all expectations in Lester’s first year, when they reached the NLCS. Obviously, the next season they took it to the next level, and won their first championship in 108 years.  Lester and Jake Arrieta were one of the best pitching duos in MLB. They were both incredible on the mound. Chicago had two aces ready to go when it mattered.

Lester spent six seasons with the Cubs. He went 77-44 as a starter with a 3.64 ERA. His playoff pitching was what was most impressive. He was always reliable in big games, and he never shied away from the spotlight. Lester was a leader in the clubhouse. He brought a championship mentality and a winning work ethic to the organization. It was exactly what the young roster needed to compete with the best. His role with the team can’t be understated because without him, there likely is no World Series championship.

1. Finding the Face of the Franchise

Date: January 6th, 2012

San Diego Padres acquire: Andrew Cashner and Kyung-Min Na

Chicago Cubs acquire: Anthony Rizzo and Zach Cates

This was one of the first great moves made by the Theo Epstein-led front office. It ended up being a lopsided trade, but nobody could’ve predicted that from the start. Anthony Rizzo hadn’t even played a full season in the majors prior to being acquired by Chicago. As a Cub, he quickly developed into a balanced hitter, and became a lock near the top of the order. He became the face of the franchise throughout their playoff runs and arguably still is today. With all of the uncertainty revolving around the roster right now, he is the one player that hasn’t been thrown into trading rumors. He’s easily one of the fan favorites, and it would be surprising to not see him retire with Chicago.

Rizzo is a three-time All-Star, four-time gold glover, and has been a silver slugger. At times, he has been the best first baseman in the league. The left-handed slugger finished fourth in MVP voting in 2015 and 2016, which both included deep playoff runs. Rizzo has a slash line of .274/.374/.492 with the team. Along with 1,231 hits, 228 homers, and 744 RBI. When his career is all said and done, he will be considered one of the greatest Cubs of all time.