6 of the worst Chicago Cubs MLB Trade Deadline deals in the last 15 years

Over the years, the Chicago Cubs have had mixed results in their trade deadline deals. On one hand, the team pulled off some shrewd deals that lead to the 2016 World Series championship. Former ace and Cy Young winner Jake Arrieta and bullpen mainstay Pedro Strop were sneakily acquired from the Orioles and became league game-changing players. On the other hand, the Cubs' front office made a lot of deals that in hindsight were not wise. With the trade deadline right around the corner, let's look at some of the worst deadline deals the Cubs have made in the last 15 years and hope they can avoid making any huge mistakes this year.

1. The Josh Donaldson trade

It's easy to forget that third baseman Josh Donaldson was drafted by the Cubs way back in 2007. Donaldson came up as a catcher in college and in the Cubs' farm system and the team traded him to the Athletics as a throw in for starting pitcher Rich Harden. Although Harden dominated down the stretch in a career year, tossing 71 innings for the Cubs with a 2.15 ERA, his success was short-lived compared to Donaldson's.

After a couple of years with Oakland, Donaldson was converted to third base full time and he soon emerged as a defensive wizard at the hot corner and an offensive force at the plate. Over the next few seasons, Donaldson made three All-Star teams and won two-time silver slugger awards as well as the AL MVP in 2015. Unfortunately, the Cubs failed to foresee Donaldson becoming a cornerstone player and they paid the price in the long run.

At the time, the Harden deal was the right call though since the Cubs were all in on their 2008 team that won 97 games, and Harden provided the team a solid starter.

2. The Ryan Theriot and Ted Lilly deal

The Chicago Cubs began their steep decline in the 2010 season, where they traded two of the best players of that era to the Dodgers at the trade deadline. Left-handed starting pitcher Ted Lilly spent 3 and a half seasons in Chicago, where he threw 700 innings with a 3.70 ERA. Lilly was a rock for the Cubs rotation in those years and his departure was an unfortunate sight. Similarly, infielder Ryan Theriot was a fan favorite among Cubs fans for several years. With his speed and ability to hit for contact, Theriot was a serviceable middle infielder and leadoff man for a time.

Despite the value of these players, the return for the Cubs turned out to be horrendous. The main player sent to the Cubs was infielder Blake DeWitt, who played just over a season's worth of games for Chicago over a three-year period. After being designated for assignment in the 2012 offseason, DeWitt signed a minor league contract with Atlanta and was out of the league by the end of 2013.
The Cubs also received pitchers Brett Wallach and Kyle Smit in the deal, neither of whom ever made it to the Major League level.

3. The Kosuke Fukudome trade

With just a few months left on his deal, Kosuke Fukudome was traded to Cleveland in 2011 for a pair of minor league players named Abner Abreu and Carlton Smith. If you don't recognize those names, that's because both men did not play at Wrigley Field or any major league ballpark for that matter. This near-nothing return was disappointing for a guy who was a starting outfielder in Chicago for over three years.

Fukudome never really panned out in Cleveland though or with the White Sox afterward. The best years of Fukudome's career were in Japan, with several 20-plus home run seasons. Even though he never reached those heights with the Cubs, he was still a part of a couple of winning teams. in the late 2000s.

4. Jose Martinez deal

In 2020, the Cubs made a deal with the Tampa Bay Rays to acquire former Cardinal Jose Martinez. Primarily an outfielder and part time first baseman, Martinez got a lot of big hits against the Cubs during his few years with the Cardinals. However, he failed to get a single hit in a Cubs uniform and 2020 was his last year in MLB. He signed a one-year deal worth $1 million with the Mets in 2021, but a torn meniscus ended his year and he was elected to free agency without appearing in a single game for the Mets. Luckily the Cube did not give up much for Martinez, as they confusingly sent the Rays a shortstop named Pedro Martinez who now plays for the Phillies Double-A affiliate.

6. The Jose Quintana/ Dylan Cease trade

Another crosstown deal from the 2017 trade deadline, this trade will undoubtedly go down as one of the worst for the Chicago Cubs. Finding themselves in the middle of a World Series hangover and in need of another starting pitcher, the Chicago Cubs front office took a big swing by trading the top pitching prospect Dylan Cease and power-hitting corner outfielder Eloy Jiminez to the White Sox for left-handed starter Jose Quintana. At the time, this deal was justified since Jose Quintana was a durable starter coming off four straight seasons where he made 32 starts each with an ERA in the mid-to-low 3 range.

But once Quintana got to Wrigley Field, he looked like a shell of his former self and he failed to have an ERA below 4 during his tenure. Although he kept his durability for the most part, the end of his run in Chicago is mired in embarrassment since he missed most of the shortened 2020 seasons after slicing his pitching hand open while doing dishes at home, prompting season-ending nerve repair surgery.

Dylan Cease on the other hand (pun intended) has emerged as one of the best strikeout pitchers in the league and he finished second in CY Young voting in 2022. Although he doesn't look as sharp as he did in 2022, Cease continues to strike out more than a batter per inning in 2023 while Eloy Jiminez is perennially hurt.

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