Cubs rumors: 3 biggest trade deadline mistakes they should regret

3) Cubs rumors: Chicago’s biggest trade deadline mistake began in the offseason

Keeping Ian Happ might be considered a mistake but with him under team control through next season, we can’t really blame them. He could get dealt in the offseason to 29 teams rather than the 15 or so buying this summer.

The biggest trade deadline mistake of all for the Cubs began in the offseason. Rather than continue the rebuild, they bought. They signed Marcus Stroman to a big deal that looks like it is already heading in the wrong direction. Seiya Suzuki’s first year in Major League Baseball is also going to waste and so might his next season or two.

The Cubs were built poorly from the beginning. Rather than deal Contreras away in the offseason when there would have been far more suitors, they held on. They flushed a lot of money down the toilet in the process.

Those poor decisions in the offseason led to even more, and in many ways, worse ones at the MLB trade deadline.

Chicago didn’t have an all-time worst trade deadline. They just didn’t take the proper steps forward to advance the franchise back to its winning ways.

Watching on at what a team like the Cincinnati Reds were able to accomplish, the Cubs could be feeling a little worse about themselves.