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

(Photo by Mitchell Leff/Getty Images)
(Photo by Mitchell Leff/Getty Images)
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Photo by Mitchell Leff/Getty Images
Photo by Mitchell Leff/Getty Images /

The past month has brought a number of heartbreaking losses for the Chicago Cubs. Where do they stack up when looking at the Joe Maddon era?

Watching the last-place Pittsburgh Pirates celebrate a walk-offwin in yet another blown game by the Chicago Cubs was almost a numb feeling to fans. This Cubs team has blown so many games late that it is basically expected of them at this point. A team that is trying to win a division sits with the most blown saves in the second half (10) and still cannot win on the road.

This last loss came after the debacle in Philadelphia when Bryce Harper hit a grand slam in the bottom of the ninth. So while it may not be fun to look back at some of these games, one may ask what were the worst regular season losses of the Joe Maddon era? While there have been plenty of great wins, there have been a handful of gut-wrenching losses. For this list, I will give a personal five worst.

The criteria for this list is pretty simple, games the Cubs had won but lost late. Not included will be blowout losses like the ones suffered on Wednesday, Saturday and last Tuesday. Since this list covers the Maddon era, we will go back to the 2015 season in terms of a range of years. Postseason games NOT included.

Photo by Jon Durr/Getty Images
Photo by Jon Durr/Getty Images /

Chicago Cubs: Nothing worse than losing when one strike away.

7-9-15. A midsummer night at Wrigley Field between the Cubs and Cardinals, does not get much better than that. The then-young Cubs were looking for a series win against their bitter rivals in a game which saw back and fourth scoring between the two sides.

After falling behind 4-0, the Cubs took a 5-4 lead in the sixth inning when Miguel Montero cleared the bases on a double to right. That score carried into the ninth inning with Pedro Strop on the mound. He got the first two hitters before walking a Matt Carpenter to face Jhonny Peralta. Strop had a 1-2 count on him, and tried to go with some heat to the slugging veteran…then…WHAM.

The ball left Peralta’s bat in a hurry and ended up in the basket near the left field well. A crowd of 37,993 stood stunned as Peralta jogged the bases and the splattered sections of red in the stands cheered. Despite getting the tying run to second in the bottom of the inning, the Cubs failed to score and lost 6-5. Nothing worse than losing in that kind of fashion to your rival team.

Photo by Dilip Vishwanat/Getty Images
Photo by Dilip Vishwanat/Getty Images /

Chicago Cubs: Even worse? Losing to the Cardinals on their turf

Every single loss of the 2018 Cubs season seemed big after losing out on the NL Central crown in Game 163. This was much earlier that season on May 5, but it did not mean it did not sting like crazy. The Cubs had a 6-4 lead heading into the ninth with Brandon Morrow on the bump, and things looked pretty good…until it didn’t.

After a walk and single, Marcell Ozuna hit a double down the left field line to tie the game off Morrow, sending it into extras. Failure to score in the top of the 10th saw the score remain tied going to the bottom of the inning, where a leadoff walk set up Kolton Wong. One violent swing from Wong and the ball was gone and the Cubs lost 8-6.

What hurt Cubs fans most about that game was listening to Wong mention how he was glad the fans supporting the North Siders that day were sent home “pissed off” and added “Cardinal Nation” afterwards. Cub fans grinded their teeth as the Cardinals continued to celebrate.

Photo by Justin K. Aller/Getty Images
Photo by Justin K. Aller/Getty Images /

Chicago Cubs: The save may have been blown, but was it Craig Kimbrel’s fault?

7-3-19. Clinging to a 5-4 lead in the ninth the Cubs were just a few outs away from a victory with Craig Kimbrel on the mound. Seemed pretty safe. Unfortunately things went awry with some very sloppy defense.

It all started with a fly ball to Willson Contreras (playing in right) that bounced off this glove and hit the ground. Ruled a double, but still a very catchable ball. With runners on second and third with one out, a groundball off the bat of Adam Frazier went to Addison Russell who was playing back on the infield. Russell decided to throw home but the runner scored easily to tie the game. It all ended immediately after that as Corey Dickerson hit a sac-fly to win it. Cubs lose 6-5.

In the postgame presser, Russell said, “I don’t regret my decision going home.” This stirred up a lot of anger and confusion from the fanbase. Yes the game would have been tied, but there would have been two outs and a chance to force extras had he gotten the sure out at first.

Photo by Dylan Buell/Getty Images
Photo by Dylan Buell/Getty Images /

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.

Photo by Jonathan Daniel/Getty Images
Photo by Jonathan Daniel/Getty Images /

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.

Photo by Mitchell Leff/Getty Images
Photo by Mitchell Leff/Getty Images /

Chicago Cubs: Thursday may be the worst loss in the last decade

Well of COURSE the Bryce Harper walk-off grand slam was going to be number one on this list. Blowing a 5-1 lead in the ninth after just needing two outs will haunt this team for a while. They had a 99.6 percent chance of winning the game after retiring the leadoff man in the ninth inning before everything went awry.

Grounders that could have been outs kept the Phillies alive, including a David Bote error, and neither Rowan Wick nor Pedro Strop could get the second or third out. Derek Holland had the displeasure of facing Harper with the bags loaded and one out. WHAM. Upper deck. Game over. Cubs lose 7-5.

This is a loss that could live in infamy for a while, depending on how the season ends. If they win the division, then it will be nothing more than an ugly footnote. If they do not win the division, everyone will point to this game. It is hard to remember a regular season loss as deflating at this one in a while.

Might have to go back to that 2004 team that lost out on the postseason in the final week, it was that historically bad. A number of gut-wrenching losses over the past decade either happened on teams that still ended up postseason bound, or on teams that were bad and it did not matter. No doubt this was the worst of the Maddon era (for now at least).

Go figure, a Chicago team losing to a Philly team in gut-wrenching fashion…have not seen that before.

Next. It's been an inflammation-themed year for the Cubs. dark

Not much fun reading stuff like this, but it is always a good discussion starter. What other bad losses since 2015 can you think of? Would love to see what you the readers have to say.  Certainly some were missed in this piece.

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