
The Chicago Cubs surprised a lot of people in the baseball world by not trading some of their best players.
Last year at the trade deadline, the Chicago Cubs traded away nearly all of their good MLB players. They traded outfielder Joc Pederson, reliever Andrew Chafin, reliever Ryan Tepera, closer Craig Kimbrel, third baseman/outfielder Kris Bryant, first baseman Anthony Rizzo, and shortstop Javier Báez between July 15 and the July 30 trade deadline.
This year, it was completely different. They did make some moves, dealing four relievers (Chris Martin, Scott Effross, Mychal Givens, and David Robertson), but even that was underwhelming.
Here are three trade deadline regrets that are killing the Cubs rebuild.
Cubs: 3 trade deadline regrets
1) The Cubs did not trade catcher Willson Contreras
The Chicago Cubs are not and will not be in playoff contention for a few years. The Cubs have a good farm system (MLB.com’s No. 10 farm system, according to their post-Draft rankings for this year) but only two of the top-10 are in Triple-A. Six of their top-10 are in Single-A or were just drafted. Yet, Willson Contreras, who is a free agent at the end of this season, is still with the club.
Offense at the catching position is at one of the lowest points in recent memory (only seven MLB teams have a wRC+ that’s better than league average at the catching position) and Willson Contreras could have helped out any number of teams at the position this year or last year.
Had they traded him last year, they would have demanded even more in a potential trade return since the acquiring club would have had an extra year of control. Now, Contreras will become a free agent and likely not re-sign with the club long-term.

2) Not trading Kyle Hendricks
In 2020, Chicago Cubs starting pitcher Kyle Hendricks was one of the best starting pitchers in baseball. In the pandemic-shortened campaign, Hendricks went 6-5 with a 2.88 ERA in 12 starts. He had a 156 ERA+, a 3.55 FIP, a 0.996 WHIP, and an average of 0.9 walks and 7.0 strikeouts per nine innings. That walk rate was the best in the major leagues. He finished ninth in NL Cy Young Award voting.
In 2021, he wasn’t pitching as well but was still decent overall. In 21 starts before the trade deadline, Hendricks was 12-4 with an ERA of 3.85. After that, in 11 starts in 2021, he had a 6.67 ERA. This season, he is 4-6 with a 4.80 ERA in 16 starts. Combined since the trade deadline last year, he has made 27 starts with a 5.58 ERA.
Now, he has a shoulder injury and is done for the season. The Cubs have to pay him $14 million for next season despite his poor play.
Last trade deadline, they may have been able to get a team to even take on his contract since he was pitching well.

3) Not trading Ian Happ
There were a number of teams looking at outfielders at the trade deadline and switch-hitters as well. Chicago Cubs outfielder Ian Happ fits both of those descriptions and he has had a great season thus far.
Happ was an All-Star for the first time this season and in 118 games, he has hit .277/.351/.449 with an OPS+ of 123. In addition to receiving that production in either left field or center field, Happ would have provided two extra benefits in a trade.
The first of those benefits is that he is not a free agent until next season. The Cubs would have been able to get a bit more in a trade because of his contract control. A playoff contender would have one less thing to address this coming offseason. With the universal DH, Happ could also be employed in that role as well.
The second benefit is that he has experience playing in the infield too. Happ has played second and third base as recently as last season. While those are not his primary positions or his best, Happ’s versatility would have provided added help.
The Cubs have to get their rebuild in order this season so, perhaps, they will be able to trade Happ. But the ship on trading Contreras has sailed, and Hendricks’ poor performance suggests he’s off the table as well.

