Spooky season: 5 scariest days of the 2021 Chicago Cubs season

#5. June 30: Chicago Cubs lose to Brewers 15-7 after seven-run first inning.

Coming into this Wednesday matinee travel day, the Cubs had dropped the previous five games after no-hitting the Dodgers in Los Angeles. The Cubs were looking to avoid being swept in Milwaukee before returning to Chicago for a massive ten game homestand.

Brewers  rookie Aaron Ashby took the mound for his first career start and the Cubs welcomed him to the bigs in remarkable fashion, putting up seven runs and chasing him after just two-thirds of an inning. He left the game with a career 54.00 ERA. Things looked great for Chicago, leading 7-0 after just one half inning.

And it just got worse from there.

Jake Arrieta, needing a big start to prove he was still a key piece in the rotation, was given a seven-run cushion (including a run he scored himself) before he even took the mound. This was a perfect scenario for him to give the Cubs five or six innings to work out some of his struggles. The first inning got messy, but only surrendered one run on a bases loaded walk. Then, messy turned to bad, which quickly turned to worse.

Arrieta only could manage two outs in the second before getting the hook, giving up five more runs. The bullpen then went on to surrender nine more runs in the game, and the Brewers came back from being down 7-0 in the first to scoring fifteen unanswered runs, beating the Cubs 15-7. This was the sixth loss in what would end up being an eleven game losing streak, ultimately sealing the fate of the Cubs season and plan to move forward.

You would think (and certainly hope) this is the only time a loss like this would take place for a team, but unfortunately that was not the case.

#4. August 27: Chicago Cubs blow another big lead and lose to White Sox 17-13.

Not a great theme to have throughout a season, but the Cubs had way too many blown-lead losses after big first innings. This one in particular happened to the crosstown rival White Sox on a Friday night in August.

Seeking revenge for being swept at Wrigley earlier in the month, the Cubs plated six runs in the first on the Sox, thanks to big hits from Patrick Wisdom, Robinson Chirinos and Andrew Romine. Prior to the game, I texted one of my friends to (responsibly) hammer the White Sox on the run line due to how bad the Cubs had been looking. After the first half-inning, not only did I profusely apologize, but I also even paid him the amount of his bet for being so wrong. It was an unsolicited suggestion gone bad in the worst way possible because I loved every second of being wrong.

Unfortunately for us Cubs fans, this was premature. I was not wrong at all.

The Sox plated eight runs in the third inning, and it was on from there. Four more in the fifth and three more in the eighth kept the ballpark rocking on the South Side as the route was in full form. Yasmani Grandal went 4-for-6 with two home runs and eight runs batted in. Former Cub traded to the Sox Eloy Jimenez went 1-for-3, walked three times, and scored three times.

The Cubs did score six runs in the last two innings, including an Ian Happ homer and a second bomb from Wisdom, but it was much too late to compete. The score does no justice to the massacre that took place at Guaranteed Rate Park that night.

#3. August 8: Sox pound the Chicago Cubs early and embarrass them on ESPN

I hated this game before it even happened. On Friday, the Cubs stormed back late to tie the game with a Andrew Romine home run that surprised him more than anyone. It felt like a momentum shifter beyond measure, until the Sox scored four in the tenth and won the game. Saturday, the Cubs were dominated by Carlos Rodon for five innings and never scored a run. Sunday, the Cubbies needed to avoid a sweep at the hands of the South Siders on national television, Sunday Night Baseball on ESPN. It did not go well.

Zach Davies took the mound looking to stop the bleeding and save his season. The wind was blowing out at approximately 1,000,000 mph and the White Sox took full advantage early. Tim Anderson homered on the very first pitch of the game. Then Eloy Jimenez. Then Andrew Vaughn. Now it is 5-0 White Sox, and the game is over by all accounts. Davies lasted just two innings, giving up seven runs on seven hits. The White Sox embarrassed the Cubs 9-3.

Jimenez finished 3-for-4 with five RBI against the team that traded him. He admits to having some extra fuel in the tank when playing the Cubs because of their decision to trade him. In his career versus the North Siders, he is a .340 hitter with six home runs in 13 starts. That is a nightmare in itself, considering the Cubs traded him for Jose Quintana in 2017 to help win a second consecutive World Series. That did not come together, and Quintana never panned out for the Cubs while Jimenez continues to light up Cubs pitching.

#2. July 29: Chicago Cubs lose to Reds and say goodbye to Anthony Rizzo

The week leading up to the July 30 MLB trade deadline was nerve-wracking and stressful for Cubs players and fans alike. There were so many questions and not many answers. The thing that was consistent was the Cubs putting the best lineup out on the field to win every day. That all changed on Thursday, July 29.

The starting lineup for the series finale against the Reds featured no Kris Bryant and no Anthony Rizzo. Immediately the internet went to work in trying to put the pieces of this puzzle together. All game long, cameras were in the dugout focused on the two Cub legends. They were always in good spirits, smiling and laughing most the game. The Cubs lost the game 7-4, but that was not the biggest loss to come on the day.

As the team boarded the bus to start their journey onto Washington to play the Nationals, someone was missing. Rizzo returned to David Ross’ office, where he was met by Ross and Jed Hoyer. They let him know he had been traded to the New York Yankees, a team not many had on their radar as a landing spot (including Rizzo).

Rizzo had been on record saying that if the ship was going down, he wanted to be on it until the end. The Cubs had different plans, and decided it was time to start looking forward in a new direction. Rizzo spent the evening with his family walking around Wrigley Field with his family one last time and gathering his belongings, one of the hardest things for Cubs fans to watch and see.

And yet, it was not going to get any easier.

#1. July 30: The Chicago Cubs core is officially dismantled

The combustion of the Chicago Cubs roster was in full bloom by this morning. We’ve already seen moves prior to this day: Joc Pederson to Atlanta, Andrew Chafin to Oakland, Ryan Tepera to the White Sox. The latest move  stung the most though, which was World Series champion and unofficial captain Anthony Rizzo to the evil empire Yankees. We as Cubs fans knew more was coming, we just didn’t know what or when yet. All we knew was if something was going to happen, it would by 4 PM.

The first was closer Craig Kimbrel to the White Sox, the second Cubs bullpen piece to head to the South Side of the week. It was tough to see a great arm leave, but there was not as much attachment as some other guys. Plus, everyone knew that was a movable piece.

Then, it started to sting. Around 2:00 local time, it was reported and confirmed that right-hander Trevor Williams and star infielder Javier Baez were headed to New York to join the Mets. Another guy wanting to stay with the Cubs in Baez was traded away for a young asset. The Cubs were dealing, but at this point it was still unclear if it was over or not. Did they get enough to keep and reconcile with Kris Bryant? Nothing was for certain until about three minutes before the deadline.

Bryant was indeed on the move and headed to San Francisco. The dismantling of the Chicago Cubs was complete, and the eyes of the front office were set towards the future. In less than twenty-four hours, Cubs fans said goodbye to three players you would trade anything to keep for life. Baez, Bryant, and Rizzo all homered in their first games with their new teams. Bryant and Rizzo made the playoffs. All three are now free agents and seeking their next home.

In hindsight, it was smart for the Cubs to receive compensation for losing three top tier players, but it does not make it sting any less. Nothing says any one of these three could not rejoin the Cubs as soon as next season, but this was easily the spookiest day of the season, and maybe even in franchise history.