Chicago Cubs: Most gut-wrenching losses of the Maddon era

Chicago Cubs: This list sure is full of 2019 losses, isn’t it?

7-27-19. One of the two nightmare losses to the Milwaukee Brewers at Miller Park a few weeks back. A game which saw Kimbrel surrender two home runs in one inning, a rare feat. This was also the game the Cubs blew a 2-0 lead in the eighth inning which spoiled a Jon Lester gem. But the biggest story of the game was in extra innings.

With the score tied in the 10th, Albert Almora hit a go-ahead solo shot to give the Cubs a 3-2 lead. The Cubs fans cheering at Miller Park were loud, but they did not last long. Immediately Christian Yelich tied the game with a solo shot. Famously from this moment was the shot of Theo and Jed looking completely dumbfounded by what happened in their box seats.

After a walk, up stepped rookie Keston Hiura. It seemed doomed for the Cubs. WHAM, it was. A line drive over the right field wall to give the Brewers a 5-3 victory sent the Cubs back to the dugouts with their heads down. Unfortunately something they have gotten accustomed to. One could argue this was the most gut-wrenching defeat at Miller Park for the Cubs since it opened in the early 2000s.

Chicago Cubs: Our ‘honorable mention’ losses

So before we got to the number one loss on this list, we will look at a few that could arguably be on the list or are close. There are some games that are probably not even on this slide that could be worthy, but we can’t list all of them!

5-5-17: “The Brett Gardner Game” which saw the veteran lefty hit a go-ahead shot with two outs in the ninth at Wrigley Field. Cubs lost 3-2.

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5-6-18: Former Cub legend Dexter Fowler hits a two-out walk off homer in the 14th inning that just got over Jason Heyward‘s glove. Cubs lose 4-3.

9-3-18: After taking the lead on an Anthony Rizzo two-run shot off Josh Hader in the top of the eighth, the Brewers tied it in the bottom of the eighth and walked it off in the ninth. This loss changed the course of the NL Central last year, had they hung on, the Brewers are probably buried. Cubs lost 4-3.

5-21-19: Cubs took the lead late against the Phillies and should have won but the umpire missed a check-swing third strike call on Andrew McCutchen. Jean Segura tied it and the Phillies won in extras. Cubs lost 5-4.

5-24-19: A 4-0 Cubs lead evaporated early, but they took the lead on a Contreras single in the eighth. Three outs from victory, Pedro Strop took the mound to close it out. A walk to Joey Votto was followed by a go-ahead, two-run mammoth shot by Cub-killer Eugenio Suarez to the back of the bleachers. Cubs would go and lose 6-5.

8-16-19: Go ahead and put Friday night’s game on this list. Awful.