What does history say about the Cubs' playoff chances?
Has any Cubs team been this far out on Labor Day and made it?



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“It’s not the hope that kills you. It’s knowing it’s the hope that kills you that kills you.” — Jackson Lamb
The Cubs woke up yesterday (not a given for all baseball players, just ask old DK57) just three games out of the National League playoffs. Our old buddy Nick Castellanos walked off the Barves on Sunday Night Baseball, Karl Ravech hooted and threw his toupee to the sky and the Cubs were as close to an actual playoff spot as they’ve been since June. Probably. I don’t really know, I didn’t look it up.
But, I did look something up for the benefit of you, the home reader. The super hot Cubs, who went 8-1 on their most recent road trip through Miami, Pissburgh and Washington are scoring runs in barrages. They scored 14 runs four times on the road trip, which is three more times than the Bears scored 14 points last year (again, I didn’t look it up.)
Anyway, on Labor Day, the Cubs owned just a 6.9% chance of overtaking the Barves and the Mets—who are in between the teams, just one game ahead of the Cubs—it’s not like they haven’t overcome a three game deficit this late in the season to make the playoffs. Is it?
Wait, have they ever done that?
This is what I researched.
And this article would have been more fun to read if Jorge Lopez hadn’t taken a 3-0 lead in the eighth and turned around and chucked it into the bleachers.
The Cubs have made the playoffs 21 times in their long, illustrious history. If you are wondering, that’s 10 more playoff appearances than the White Sox have ever had. But sure, the Cubs are the lovable losers. Whatever. The current Sox are about to make history by losing the most games in big league history. They need to go 12-11 to avoid tying the 1962 Mets “record”, which would require them to win games at more than twice their current pace. Anyway, the biggest difference between the two Chicago teams is that when the Cubs are bad the fans still give a shit.
In those 21 playoff seasons, the Cubs were ahead on Labor Day in 16 of those years. And if you’re wondering, yes, Labor Day’s been a thing for all of those seasons, as Grover Cleveland signed the bill in 1894 and it’s always been the first Monday in September. The Cubs were tied for a playoff spot once and had to come from behind in four others. We’ll get to those in a minute.
And, some of these seasons have Remember This Crap podcasts if you really want to do your research. Hell, 2003 has two podcasts devoted to it.
2020 - David Ross’ plucky Cubs had a 2.5 game lead on Labor Day in the shortened season, but they still had a normal amount of games to go. They tried to shit the bed from them until the end of the season, The Cubs started to fade, but then Willson Contreras homered against the Sox and threw his bat into orbit and all of that.
2018 - The Cubs last playoff team of the Joe Maddon Era had a four game lead in the NL Central on Labor Day. They blew it, then lost the tiebreaker game to the Brewers at home and then a torturous extra inning loss to the fucking Rockies and Tony Wolters in the Wild Card Game. But it was still the playoffs. I guess.
2017 - The Jose Quintana trade had spurred the Cubs back over the Brewers (really, it did—and Jose was especially hard on the Brewers that year 1.20 ERA in 15 innings) and they had a 3.5 game lead on Labor Day. They’d win the division and then beat Dusty Baker’s Nationals in the last fun playoff series they’ve had. Then Jose’s wife had a panic attack on the plane and John Lackey pitched to Justin Turner and you know the rest.
2016 - 16.5 games. Felt like a million. Your daily reminder that we had a proper team to root for once.
2015 - Left for dead when Cole Hamels ended their really long streak of not being no-hit on July 25, the Cubs lost the next day to the Phillies, too and then blew a three run lead in the ninth to the Rockies (Jason Motte and Rafael Soriano couldn’t close the door—gee, ya think?), but then Kris Bryant did this in the bottom of the ninth:
And the Cubs, who were three games behind the Dodgers for the second wild card and also had the Giants and Nationals in the way, went 27-11 until Labor Day, had a half game lead over the Dodgers and never looked back, winning 18 of their last 26 games on their way to scheduling postseason matchups with the Pirates and Cardinals in an effort to make Kyle Schwarber the postseason legend he continues to be to this day.
2008 - The Cubs played like the best team in the National League most of that season and had a 4.5 game edge on Labor Day. They cruised into the playoffs, then Ryan Dempster walked seven Dodgers and they went home.
2007 - I was honestly surprised that these clowns had a lead on Labor Day, but sure enough, they did. How Lou Piniella dragged this bunch of misfits into the playoffs is a true wonder. They led the Brewers on Labor Day,and were tied as late as September 18. The Cubs got swept in a three game series in Florida, September 25-27 but the Brewers lost two of three to the Cardinals and blew their last decent shot at catching up. When Carlos Zambrano and two relievers (one of them was Dempster) shut out the Reds, their old buddy Greg Maddux was beating the Brewers in Milwaukee and the Cubs clinched that night, September 28.
1998 - If you lived through this playoff “push” and Sammy Sosa’s 66 homers, you’ll never forget it and you probably have four or five years shortened on your lifespan. The 1998 Cubs were incredibly fun, but they weren’t what you’d call “good.” They were tied with the Mets on Labor Day for the Wild Card, and they went 10-9 the rest of the way, the Mets went 8-10 and the Giants went 11-8. The Giants would have won the spot outright but Neifi Perez saved the Cubs season with a walkoff homer for the Rockies in the final moments of the last day of the season. The Cubs and Giants were tied, and had a one-game play-in at Wrigley, Steve Trachsel nearly threw a no-hitter and nobody noticed because he walked six guys, Gary Gaetti hit a homer, and Terry Mulholland and Rod Beck both pitched in the ninth to finish it off. For Mulholland it was his 12th appearance in his final eight days (with five starts), somehow, and for Beck it was the 39th time he’d pitched in September that year. I didn’t look those last two stats up. I just remember.
1989 - Until Joe Maddon came to town, these were the most fun Cubs of our lifetimes. While the ‘84 Cubs were better, they were like watching the Phillies JV team end the Cubs postseason drought. These (at least new ones) were our Cubs. An old Cub, Rick Sutcliffe (did you know he has a grandson named Ryder?) outpitched David Cone on Labor Day, but that next Friday, the Cardinals cut the Cubs lead to a half game. What happened Saturday, September 9th?
The Luis Salazar1 Game.
The Cubs denied the Cardinals first place that day and broke their will in the process. Four games later the lead was up to 5.5 games and it was all over.
1984 - No Cubs fan under 50 had any idea how to behave in a playoff race, so even though they went 20-10 in August to push their lead from a half game to 5.5 games, everybody was still panicked about 1969. Everybody but the actual Cubs, who had a six game lead on Labor Day and pushed it to 9.5 by September 15. They gave everybody a little scare by then losing five in a row down the stretch, but on Sunday, September 23 they swept a doubleheader in St. Louis and the next night Sutcliffe did this:
1945 - Charlie Grimm’s 4-F All-Stars woke up on Labor Day 1.5 games ahead of the Cardinals, but went to bed up 3.5 games after they swept the lowly Reds and the Cardinals lost a doubleheader in Pissburgh. Andy Pafko hit a grand slam in the first game and Bill “Swish” Nicholson hit a two run shot in game two. The second game was started by Hank Wyse who didn’t get anybody out, but Hy Vandenberg pitched nine scoreless innings of relief to get the win.
The Cardinals closed to within 1.5 games on September 26, but the Cubs won the final five in a row to take the pennant.
1932 - In mid-August the Cubs had three straight walk-off wins over the Boston Braves on game winning hits by Billy Jurgess, Hub Pruett, and Riggs Stephenson that pushed their NL lead to 2.5 games over the Dodgers, but the big hit came two days later when, trailing the Phillies 5-2 in the ninth, an error by second baseman Bernie Frieberg on a ball hit by Gabby Hartnett kept the game alive and shortstop Mark Koenig won it with a three run homer. The Cubs’ lead would have dropped to a half game with a loss. They won the next 11 games in a row and opened up a 7.5 game lead that was six games on Labor Day. They went on to get swept by the Yankees in the World Series and some fat guy pointed at center field or something.
1929 - Joe McCarthy had managed the Yankees in the 1932 World Series (the first of the seven he won in New York), but he was managing this Cubs squad in '29. The Cubs had long ago served notice in the National League. They were up 12.5 games on Labor Day and easily won the pennant. They lost in five games to Connie Mack’s A’s who also won the World Series in 1930 and lost in the World Series in 1931. By 1934 Mack had sold off all of his good players and from 1935 to 1965 they would lose at least 100 games nine times and at least 90 games 20 times. The A’s lost between 91 and 108 games in nine straight seasons from 1935 to 1943.
1918 - The season ended on Labor Day with the Cubs 10.5 games clear of the Giants, after only playing 129 games. The season was shortened as a result of World War I, and the World Series was played from September 5-11. The Cubs lost in six games to the Red Sox. Five of the games were decided by one run and the other was a 3-0 shutout by Hippo Vaughn in game five that forced the series back to Boston. In game six, both Red Sox runs scored on an error by Cubs right fielder Max Flack. Fred Merkle (the Boner King) drove in a run for the Cubs in the fourth to make it 2-1, but that was all for the scoring. The Cubs managed just one more hit against Carl Mays the rest of the way.
1910 - Frank Chance’s final World Series team easily won the pennant and had a 9.5 game lead over the Pirates on Labor Day. They lost the World Series to the A’s in five games. Home Run Baker was the hitting star for Philadelphia batting .409 and slugging .636 in the series with no home runs.
1907 - The second in a run of three pennants in a row (and four in five years), the Cubs won nine fewer games than had the year before and still won the National League by 17 games. Of course, they had 107 wins, which will do that. They won the club’s first World Series in a sweep, kind of. The teams played to a 3-3 tie in 12 innings at West Side Grounds. It got dark so they stopped. They started over the next day and the Cubs won four straight.
1906 - On their way to a record 116 wins (Lou Piniella’s 2001 Mariners tied them, but played eight more games), the Cubs led the NL by 13 games on Labor Day and won the pennant by 20 games. They played the White Sox in the World Series and lost in six games to the “Hitless Wonders.” The teams alternated home games with the Cubs hosting at West Side Grounds and the Sox at South Side Park III. The Sox led the series 3-2 with every team winning on the “road” until the Sox scored seven runs in the first two innings off of Mordecai Three Finger Brown and won game six 8-3, and thus the series.
OK, so what about the years the Cubs weren’t in first place on Labor Day?
2003 - Dusty Baker’s Cubs were 1.5 games behind both the Astros and Cardinals in the NL Central and trailed the Marlins by two games in the Wild Card race. Labor Day was the first game of an epic five game series with the Cardinals that set the tone for the rest of the season. Mark Prior pitched eight scoreless innings and Kyle Farnsworth finished off the shutout in game one. Cardinals starter Woody Williams couldn’t get through the fifth and so was fresh enough to pitch again in the fourth game of the series out of the bullpen and took the loss both times. The teams played a doubleheader on Tuesday and game one went 15 innings until Sammy Sosa did this:
They lost the second game in controversial fashion when down 2-0 in the seventh, Moises Alou hit what appeared to be a game tying double down the left field line that was ruled foul by third base umpire Jay Klemm. In the aftermath, both Moises and El Pulpo, Antonio Alfonseca were thrown out of the game for arguing with Klemm (the ball had landed in clear view of the Cubs bullpen.) El Pulpo inadvertently hit Klemm with his belly.
Note that Chip got the call wrong originally. Of course he did.
The Cubs would win the final game of the series 7-6 in a see saw affair on Tony Womack’s game winning single in the seventh. The Cubs briefly went into first place at the end of the next weekend, but didn’t get the lead for good until Kerry Wood pitched seven scoreless in a 6-0 win over the Reds on September 23. The next day, Shawn Estes throw an inexplicable shoutout in Cincinnati. The Cubs clinched four days later after sweeping a doubleheader at Wrigley against the Pirates.
1938 - The Cubs found themselves in an even worse position than they face today. They trailed both Pissburgh and St. Louis by five games on Labor Day. But they got to work right away. They swept the Pirates in a doubleheader at Forbes Field, then went to St. Louis and swept the Cardinals in three games. All in all, the Cubs went 21-5 in September and turned what was a seven game deficit at the start of the month in to a 1.5 game lead by the end. The hit that put them into first place for good was Gabby Hartnett’s “Homer in the Gloamin’” on September 28 at Wrigley against the Pirates. They clinched the pennant on the second to last day of the season when they pounded out 17 hits (four by second baseman Billy Herman) in a 10-3 win at Sportsman’s Park in St. Louis. They got swept in the World Series by the Yankees. Again.
1935 - The Cubs were in a similar spot to Craig Counsell’s boys, trailing two teams (Cardinals and Giants) by 2.5 games. They played a doubleheader on Labor Day and split with the Reds. And then the next day they beat the Phillies and the next day and the next day and they swept four straight four game series (against the Phillies, Braves, Dodgers and Giants) and kept on going, winning five more in a row to bring their winning streak to 21 games. By the end, they had gone from 2.5 games behind to six games up and they actually clinched the pennant with four games to spare. There you go, Craig. Just win 21 in a row. Never fails.
They lost the World Series in six games to the Tigers.
1908 - The defending World Champions were in a tight race all season and on Labor Day were in third place in the NL behind the Pirates by a half game and the Giants by a full game. If you know nothing about the incredible 1908 season, read the Cait Murphy book Crazy ‘08: How a Cast of Cranks, Rogues, Boneheads and Magnates Created the Greatest Year in Baseball History. It was a truly incredible year, made more famous by a future Cub, a Giants youngster named Fred Merkle. The 19-year-old was making his first career start, playing first base in a late season game against the Cubs at the Polo Grounds with the teams tied with six games to go. Merkle came up to bat with two outs in the ninth with the game tied at one. He singled to put runners on the corners. Giants shortstop Al Bridwell singled to center scoring Moose McCormick with the winning run. Fans rushed the field to celebrate the Giants return to first place. Cubs second baseman Johnny Evers noticed that Merkle hadn’t run all the way to second before celebrating the Giants win. Through the horde of fans running around on the field, Evers retrieved the ball (or, at least a ball) and ran to second base to force Merkle out. The umpires agreed. Since a run can’t score from third when the inning ends on a force out, the score went back to 1-1. The umpires ruled that the game could not be restarted after getting all the fans off the field before it got too dark to play, so the game was declared a tie and replayed on October 6. Even then, the Cubs and Giants were still tied for first. Cristy Mathewson started the game for the Giants, his fourth start in ten days. He only went seven against the Cubs allowing four runs on seven hits. Jack Pfiester started for the Cubs, allowed a hit, two walks and a hit batsmen and was removed with two outs in the first. Mordecai Brown allowed one run in 8.1 innings of relief to win the pennant for the Cubs, 4-2.
So, in 131 seasons since Labor Day became a Federal holiday, the Cubs have only once overcome more than a three game deficit on Labor Day to make the playoffs. And all that took was one of the best Cubs teams of all-time, at the end of one of the greatest runs of Cubs’ baseball of all time.2
But you can’t say they’ve never done it, now can you?

When Shohei Ohtani played at Wrigley Field this season, some fans booed? Why? Well, because some Cubs fans are absolute fucking morons, but I guess it was because Shohei was smart enough to sign for an ungodly amount of money from the Dodgers instead of (to Tom Ricketts’ undying relief) from the Cubs. Shohei is simply an amazing player, and the first true two-way star, ever. Hell, this year he’s recovering from Tommy John Disease so he had to concentrate on hitting only and he’s going to be the MVP and already has put up a 40-40 season, on his way to 50-50.
But most importantly, his dog can do this.
Good boy, Decoy.