They Should Have Passed

The recent announcement that Edwin Jackson was DFAed finally ends the long saga of undoubtedly Theo Epstein and Jed Hoyer’s worst acquisition for the Cubs. Jackson, signed to a 4-year/$52 million contract prior to the 2013 season, struggled mightily in 2013 and 2014 before being demoted to the bullpen. Overall, he finished with a 5.37 ERA in 347 innings with the Cubs. Yet Jackson isn’t the only player the front office should have passed on. Below I review the top “misses” since Epstein/Hoyer took over in late October 2011. I've listed them in chronological order rather than ranking them: feel free to weigh in on which you think is the worst or if there are any clunkers that I missed (I've tried to purge some recent players from memory, so omissions are possible).  

Lendy Castillo

The Cubs selected Castillo from the Phillies in the 2011 Rule 5 Draft. Converted from a shortstop to a pitcher in just 2010 by the Phillies and at only 23-years-old, the Cubs were intrigued by his potential. Forced to keep him on the major league roster or return him to the Phillies, the Cubs used one of their bullpen spots for him to begin the season. He pitched in only 7 innings over the first 6 weeks of the season, before being placed on the disabled list. He returned from the DL and rehab in mid-August and pitched another 8 innings over the last two months of the season. After keeping him on the major league roster for all of the season, the Cubs were then able to demote him to the minors in 2013—a price the regime seemed willing to pay to obtain another young arm for the system. Castillo struggled in 2013-2014, however, with an ERA just under 6.00 in 2014 and nearly 4.00 in 2014. Granted free agency, Castillo signed with the Rangers and is pitching in AA in his age 26 season. Moreover, the Phillies filed a grievance against the Cubs for abusing the DL with Castillo in 2012 and were awarded the Cubs 2013 first round Rule 5 Draft pick. Castillo ended up being more of a headache than he was worth.

Ian Stewart

Obtained in December 2011 from the Rockies for Tyler Colvin and DJ LeMahieu, Stewart was supposed to be the Cubs answer at third base. In his prime at age 27, Stewart had ripped off three straight double digit home runs seasons prior to his 2011 campaign where he struggled and was demoted to AAA. All Stewart did with the Cubs was hit .201 before landing on the 60-day DL with a wrist injury. Signed to $2 million contract for 2013, Stewart hit just .168 in AAA before making critical comments about the organization on twitter, prompting his release.

Chris Volstad

The Cubs weren’t going to get much for Carlos Zambrano, but they couldn’t have done much worse than Volstad. Acquired in a trade with the Marlins in January 2012, Volstad was still just 25 and the hope was he would bounce back from a 5-13, 4.89 ERA season. Somehow, Volstad managed to do worse, going 3-12 with a 6.31 ERA in 21 starts with the Cubs in 2012. After bouncing around with several organizations, he is now having some success as a starter in AAA for the Pirates.

Scott Baker

Why did the Cubs spend $5.5 million dollars on Scott Baker for the 2013 season? He was recovering from an April 2012 Tommy John surgery and the Cubs knew he would not be ready until late in the 2013 season. Perhaps gambling that he would come back soon and be able to be flipped at the trade deadline, or that he would have success in the later part of the season and then re-sign on friendly terms, the Cubs were disappointed. Baker was only able to make three starts in September and then promptly left as a free agent. He struggled for the Rangers in 2014 and is now in AAA for the Dodgers.     

Kyuji Fujikawa

The 32-year old Japanese closer Fujikawa was signed to a 2-year/$9.5 million contract prior to the 2013 season. Fujikawa was not one of the more coveted Japanese players on the market and given his age many felt at the time that the Cubs over paid. In the end, he made just 12 appearances for the Cubs in 2013 before having Tommy John surgery. He made it back for 15 games at the end of the 2014 season, but struggled, and left as a free agent in the off-season. He is now playing Kochi Fighting Dogs of the Shikoku Island League in Japan.

Jose Veras

Veras had 21 saves and a 3.01 ERA in 67 games between the Tigers and Astros in 2013 and was signed to a 1-year/$3.25 million contract to be the Cubs closer in 2014. He proceeded to post a 15.88 ERA over his first 6 games, spent time on the DL, then continued to struggle in May before being released in June. Overall, he had an 8.10 ERA with the Cubs. He had some success for the Astros after his release and is now on their AAA team.

(Dis)Honorable Mentions

Phil Coke: $2.25 million garnered 10 IP and a 6.30 ERA in 2015.

Ryan Sweeney: The Cubs are paying Sweeney $2 million dollars for 2015-16 not to play for them simply because it seems they couldn’t accurately count the number of back-up outfielders they had this past off-season.