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Top 25 Baseball Stories of the Decade — No. 1: Chicago Cubs finally win it all

Chicago Cubs World Series Atmosphere

CHICAGO - NOVEMBER 03: The Wrigley Field marquee, displaying ‘World Series Champions’ after the Chicago Cubs’ world series win against the Cleveland Indians in Chicago, Illinois on November 3, 2016. (Photo By Raymond Boyd/Getty Images)

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We’re a few short days away from the dawn of the 2020s. So, instead of counting down the Top 25 stories of the year, we’re taking a look at the top 25 baseball stories of the past decade.

Some of them took place on the field, some of them off the field and some of them were more akin to tabloid drama. No matter where the story broke, however, these were the stories baseball fans were talking about most over the past ten years.

And finally, here we are. The biggest baseball story of the decade: The Chicago Cubs Finally Win It All

So much of this countdown has dealt with controversy, scandal or problems in the game. Sorry, I can’t help that.

I’m the one who came up with this list and if you’ve been reading what I write for any amount of time you know that, while I love the game of baseball, I’m critical by nature. In my experience the most effective way to make institutions one cares about better is to call them out when they fail. I know not everyone agrees with that philosophy, but there is no shortage of people who write about the game who do so from a fan’s or a cheerleader’s or a P.R. guy’s or an armchair general manager’s perspective, so if my approach bugs you I’d encourage you to read those writers. As a matter of personal temperament, I’m never gonna be that guy. At its best baseball is the best thing and I get particularly peeved when it’s not at its best, so I’m gonna talk about it when it’s not.

But I’m not made of stone. Baseball moves me, often. I’m moved by its history. Its drama. By the passion its fans have for the game and the teams and players they root for. When there’s a big moment, a big comeback, or a triumphant underdog, I feel it and I savor it.

One of those moments happened on November 2, 2016 when the Chicago Cubs did what almost no living human being had been around for and likely no one ever actually witnessed: they won their first World Series in 108 years.

I don’t believe in curses. I don’t think black cats released near the on-deck circle in 1969 or billy goats denied entrance into a ballpark in 1945 have an effect on baseball games or the men, born decades after the fact, who play them. It’s a lot of fun to talk and joke about such things that become part of baseball lore, but if you’re the sort of person who takes such things seriously we don’t have a lot to discuss, you and I.

That being said, 108 years between World Series titles is quite a thing. A thing that, over time, would’ve generated enough agita on its own. It was only fitting then, that breaking that title drought — or, if you must, breaking that curse — didn’t come easy. For starters, it required a recession, a sale and then a complete rebuild and re-imagining of the Chicago Cubs organization.

The Cubs managed to make the playoffs in both 2007 and 2008, but GM Jim Hendry’s teams were not really built for the long haul. They carried a high payroll and in 2008 six of their eight everyday players and two of their five starting pitchers were over 30. Two more of those starting pitchers -- Carlos Zambrano and Rich Harden -- had either a lot of mileage on their odometer or were simply biding time between inevitable injuries. I’m not one to knock players over 30 out of hand, but manager Lou Piniella seemed to have gotten about as much as could be gotten out of this squad and that only amounted to two consecutive exits in the NLDS.

And it’s not like there was a lot of latitude to do more. The Cubs’ owner, Sam Zell, had a financial mess on his hands. He had acquired the Cubs as part of a leveraged buyout of the Tribune Company, the media conglomerate which had owned the Cubs for years, and as a result of all the debt he had incurred, the Great Recession, and the fact that owning media conglomerates was not exactly a business Zell was suited for, he needed to sell off the Cubs in order to make ends meet. After a drawn out and somewhat tortured process, the Ricketts family’s bid for the team was approved on January 22, 2009. They would officially take over the club on October 27 of that year, just in time to watch the Yankees win their 27th World Series in the time since the Cubs last won a single one.

The Cubs lost more than 90 games and finished in last place in each of the first two seasons the Ricketts family owned the team. Tom Ricketts fired longtime general manager Jim Hendry in August of 2011. A month later the Chicken and Beer Red Sox led to a public bloodletting in Boston which cost manager Terry Francona his job and made Sox GM Theo Epstein want to get the hell out of Boston. The Sox’ brass, unwisely, thought that was a fine idea and struck a deal with the Cubs to let Epstein out of his Red Sox contract in exchange for some money and some players who ended up not mattering all that much in the grand scheme.

Epstein quickly hired Padres GM Jed Hoyer and assistant GM Jason McLeod -- both of whom were former Epstein lieutenants in Boston -- as GM and director of scouting, respectively. On Oct. 25, 2011, Epstein was introduced at a press conference. At the time he said “I firmly believe that we can build a consistent winner, a team that will be playing baseball in October and a team that ultimately will win the World Series.” The ghosts of that black cat and that billy goat had no comment, but anyone familiar with the history of the Cubs was dubious.

Epstein, Hoyer and his staff got to work pretty quickly and did a hell of a lot of work. You know about stuff like trading for Anthony Rizzo and developing Kris Bryant, of course. And you can read all of the specific ways they assembled the team they brought into the 2016 season in this position-by-position breakdown written by Cliff Corcoran and Jay Jaffe at Sports Illustrated three years ago. But Corcoran’s and Jaffe’s executive summary puts the scope of the rebuild in perspective:

Three players—catcher Willson Contreras, infielder Javier Baez and outfielder Matt Szczur—were holdovers from the previous administration. The rest of this year’s current 25-man roster was assembled by Epstein and Co. thanks to 12 trades, eight free-agent signings that cost $495 million, one amateur draft pick and one Rule 5 draft pick.

Before any of that would bear fruit, the Cubs still had to endure last place finishes in 2012, 2013, and 2014, giving them five in a row. Before the 2015 season the Cubs hired Joe Maddon away from the Tampa Bay Rays. It was a deal made possible by Maddon and his agent finding a loophole that allowed him out of his Rays contract. But let’s be serious: Maddon and his agent would not have been looking for such loopholes if the Cubs weren’t signaling a strong interest in him. So strong an interest that they cast aside manager Rick Renteria after only one season at the helm in order to get their man.

With Maddon at the helm and the talent the Cubs had been stockpiling while they lost a ton of games quickly maturing, things changed radically in 2015. The Cubs went from 89-game losers to 97-game winners, finishing in third place in the stacked NL Central, snagging the second Wild Card, beating the Pirates in the one-game playoff and beating the arch-rival Cardinals in the NLDS before losing to the Mets in the NLCS. It was a hell of a ride -- one that came at least a year earlier and probably two years earlier than Epstein and Hoyer initially figured it would, they’d later say -- but the ride would only get better the following year.

The Cubs started out the 2016 season 8-1, their best start since the 1969 Black Cat season. Their luck seemed to have changed since then, though: In April starter Jake Arrieta would toss a no-hitter. On July 31 -- six days after the key acquisition of closer Aroldis Chapman from the Yankees -- they came back from a 6-0 deficit against the Mariners to win in extra innings on a Jon Lester bunt of all things.

Of course it wasn’t all luck. The Cubs were loaded. They had two legitimate MVP candidates in Bryant and Rizzo -- Bryant would win -- finished first as a team in on-base percentage and OPS+, second in runs behind only the Rockies, and featured the best overall pitching staff in the majors. They’d boast one of the best run differentials in recent history. They’d go on to win their division by 17.5 games and won a Major League-best 103 games. It was the Cubs’ best regular season by winning percentage in over 80 years.

There was obviously more work to be done, but they got to it pretty quickly, dispatching the Giants three games to one in the NLDS -- ending their even-year buls**t -- came back from a 1-2 deficit in the NLCS against the Dodgers, winning games four, five and six -- the last one via a dominant combined pitching performance from Kyle Hendricks and Chapman -- and punching their ticket to their first World Series since 1945.

Within a few days, though, it seemed like these juggernaut Cubs would face the same fate as the 1945 (and 1910, 1918, 1929, 1932, 1935, and 1938) counterparts: a World Series loss. That because the AL pennant-winning Cleveland Indians built a three games to one lead and not many teams have blown 3-1 leads in playoff series in any sport.

But it also never quite felt like Cleveland had a handle on it the way other teams with a 3-1 series leads usually have. The Indians only had three starting pitchers due to injuries and they had to ride them hard. That 3-1 lead was based mostly on cold Cubs bats and those bats weren’t likely to stay cold forever. Anything can happen in a short series, but the Cubs made it go longer, gutting out at bats and picking up wins in Games 5 and 6. The longer two teams play the more likely it is that the better team will win, and the Cubs were the better team.

Game 7 meant facing Corey Kluber who, while he didn’t win the Cy Young Award, was still arguably the best starting pitcher in the American League. And he had been dominant in the playoffs to date. Unfortunately for the Indians, Kluber was gassed for Game 7, allowing four runs in four innings. But even then it wasn’t easy. The Indians rallied for two runs in the bottom of the fifth and three in the bottom of the eighth, thanks to an equally-gassed Aroldis Chapman, to tie it up and force extra innings.

Then the rain came. It was not a long rain delay -- only 17 minutes -- but it was long enough for Cubs right fielder Jason Heyward to call a team meeting and to give them a motivational speech:

“We’re the best team in baseball, and we’re the best team in baseball for a reason! Now we’re going to show it! We play like the score is nothing-nothing! We’ve got to stay positive and fight for your brothers! Stick together and we’re going to win this game!”

It wasn’t exactly Knute Rockne -- I added those exclamation points myself despite having watched Heyward throughout his career and forcing myself to conclude that he’s really not and exclamation point kind of guy -- but it was exactly what the Cubs needed. Heyward’s words lit a fire under his teammates who shouted back things like “Keep grinding!” and “Chappy, we’ve got you! We’re going to pick you up!” and “This is only going to make it better when we win!”

Heyward’s recollection of the speech afterward:

“I told them I love them. I told them I’m proud of the way they overcame everything together. I told them everyone has to look in the mirror, and know everyone contributed to this season and to where we are at this point. I said, ‘I don’t know how it’s going to happen, how we’re going to do it, but let’s go out and try to get a W.’”

Kris Bryant’s reflection on Heyward’s speech:

“It was the best thing for us. We all got together in the weight room, we all supported each other. Chapman was a little upset. That guy works his butt off. Jason Heyward led the way, talking us up, getting us ready, and you saw what we did there.”

And it did get them ready. As soon as play resumed, Kyle Schwarber lead off with a single to right field. Ben Zobrist followed, slapping a double down the left field line, plating the guy who pinch-ran for Schwarber. Miguel Montero then ripped a single to left field to make it 8-6. That score would hold and the Cubs would be World Series champions for the first time in 108 years.

At the time it felt like it might’ve been the first of many. The Cubs were loaded with talent, the owners had gobs of money and Epstein and Hoyer were and remain two of the brightest front office lights in the game. They would continue to rampage through the National League, many of us thought, and if they falter they have the brains, the money and the youth to overcome it and reload.

Baseball doesn’t stick to such scripts, however. Over the past three seasons the Cubs have experienced quicker exits each year, losing to the Dodgers in an NLCS rematch in 2017, losing the Wild Card game to the Rockies in 2018, and, this past season, not even making the playoffs, finishing in third place, seven games back of the Cardinals and five games out of the second Wild Card. Joe Maddon’s contract was not renewed and 2016 backup catcher David Ross -- who has no coaching experience whatsoever -- is now the manager. With a payroll near the Competitive Balance Tax threshold, the Ricketts family has signaled that it’s less-than-eager to spend much if anything to patch the holes that need to be patched. Despite most of the core of the 2016 World Series winners remaining in place, the future of the Cubs is uncertain.

But nothing will take away 2016. Nothing will take away the actual World Series win and the joyride the Cubs took to get there. Perhaps, most importantly, thanks to 2016 the Cubs will never again can be cast as the thing they were for most of the last century: Perpetual losers. A punchline in movies, TV shows and literature that was so potent that merely portraying them as winners constituted the entire joke. A universal shorthand for “sad sack, made tolerable only because the losing was allegedly “lovable” and they had a neat old ballpark.

That all ended this past decade. A decade which, for the first time in over a century. the Cubs and their fans could call themselves winners. It was, by my estimation anyway, the biggest baseball story of the past ten years.

Happy New Decade, everyone.


No. 2: Analytics Goes Mainstream
No. 3: Baseball Teams Become Cash Cows
No. 4: Bud Selig Retires, Rob Manfred takes over
No. 5: The Tanking Epidemic
No. 6: The Deaths of Young Players
No. 7: Miguel Cabrera Wins the Triple Crown
No. 8: The Biogenesis Scandal
No. 9: Bullpen Mania Takes Over the Game
No. 10: The Rise of the Young Player
No. 11: Baseball Goes From Deadball To Juiced Ball
No. 12: Baseball Begins Rewriting the Rulebook
No. 13: Baseball Adds a Second Wild Card
No, 14: Albert Pujols Signs With the Angels
No. 15: Baseball Continues a Remarkable Run of Labor Peace
No. 16: Baseball implements a domestic violence policy
No. 17: Cardinals Employee Hacks Astros’ Database
No. 18: Frank and Jamie McCourt Bankrupt the Dodgers
No. 19: Baseball Embraces Gambling
No. 20: The Hall of Fame Logjam
No. 21: The Bat-flippers Win the Battle Over the Unwritten Rules
No. 22: Astros switch leagues
No. 23: The Strasburg Shutdown
No. 24: Chicken and Beer
No. 25: All-Star Game no longer counts
Honorable mention: Astros Sign Stealing Scandal

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