Congratulations on Winning the World Series, Cubs. Building a Dynasty Is a Whole Lot Harder.

93259520Cubs General Manager Jed Hoyer, left, and President of Baseball Operations Theo Epstein during the World Series victory parade on Nov. 4 in Chicago.

Dylan Buell/Getty Images

It sounds like a Ringo Starr song, but in fact it was Anton Chekhov who wrote that of all endeavors in life, “only entropy comes easy.” The Chicago Cubs of Theo Epstein, Jed Hoyer, and Joe Maddon, having won the franchise’s first championship since 1908, will commence a title defense that will succeed only if it defies Chekhov’s maxim and resists the tendency of even the best baseball teams to break apart.

The Cubs have talent, brains, and a carefully articulated plan for success, all of which represent a huge departure from most Cubs teams of the previous 108 years. (It’s a fruitless task to try to name the last great Cubs front office prior to Epstein and Hoyer, the team’s current president of baseball operations and general manager.) The franchise’s strategy in the Epstein and Hoyer era has been centered on creating a winning culture by developing a high-quality farm system and emphasizing the character of the players the team acquires. These talented young hitters and pitchers would be paid cost-effective pre-arbitration and free-agent salaries, and they would come with Cubs software—management’s combination of philosophical and practical approaches to baseball—installed in their brains via coaching, the use of advanced technology in training, and a proprietary manual whose first edition ran 259 pages. Sayeth the manual:

The Cubs attitude is positive, powerful, action-oriented, and resilient. It is an attitude that says, “I am” and “I do.” It is an attitude that says, “No matter what happens, I will continue to grow, and I will always find a way.”

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In Tom Verducci’s The Cubs Way, a well-reported but hagiographic account of the team’s championship season, we observe Epstein, Hoyer, and the field manager Maddon serve that plan almost unerringly. Players acquired via trade, such as first baseman Anthony Rizzo, are both men of high character and men who produce on the field, as are draftees such as 2013’s No. 2 overall pick, Kris Bryant. Further additions such as Addison Russell—a top shortstop prospect with the Oakland A’s whose maturation required projection rather than faith—and failed Baltimore Orioles starting pitcher Jake Arrieta—who demanded the reverse—not only worked out well but extremely well. As Epstein told Verducci, to rebuild the club quickly, “We knew we had to hit at an awfully high rate.”

To their credit, they did. However, when assessing the sustainability of this approach—that is, the likelihood that the Cubs will realize their dynastic ambitions and build a team that wins a fistful of championship rings—it’s important to scrutinize the times they didn’t hit. Those instances are largely glossed over in Verducci’s account, but they reveal just how easily things can go wrong even for the highest-functioning team in Major League Baseball and the extent to which luck protected the 2016 World Series champs from their errors.

Consider the case of Russell Martin. The Cubs put in a bid to sign the free agent catcher before the 2015 season, only to be rebuffed when the native Canadian signed with Toronto for five years and $89 million. Martin, who going in to 2015 was coming off his best season in six years, hasn’t been able to duplicate that success with the Blue Jays and will likely to continue to decline going forward. His presence in Chicago last year likely would have blocked rookie catcher Willson Contreras, who hit .282 with a .357 on-base percentage and a .488 slugging percentage in 76 games after a mid-June promotion. It was Martin’s desire to play in his home country, not Cubs management’s innate brilliance, that saved them from a blunder that would have hurt the franchise in multiple ways.

Similarly, the Cubs could afford to sign Jon Lester in December 2014 because Masahiro Tanaka had turned them down the previous January. Tanaka has been successful with the New York Yankees, but Lester has been the better, more durable pitcher over the last two seasons.

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A passing reference to failed second base/center field prospect Arismendy Alcántara also shows how human fallibility can disrupt future plans. Alcántara was signed by the Cubs out of the Dominican Republic as a 17-year-old in 2008, long before Epstein came on the scene. Beginning in 2012, Baseball America ranked him among the team’s top 10 prospects for three straight years. The Cubs called him up in July 2014. “At the time we were excited about Alcántara,” Hoyer tells Verducci.

While the transient nature of Hoyer’s affections goes unexplored, the record tells the story: Given 70 games in the majors, Alcántara didn’t hit and largely hasn’t hit since. “I think he started doubting himself,” Jason McLeod, the team’s vice president of scouting and player development, told CSN Chicago. Last June, the Cubs traded him to the Oakland A’s in exchange for veteran utility man Chris Coghlan, a 31-year-old who was then hitting .146. The trade was a surrender. Neither the manual nor enlightened coaching nor the player’s innate skill had helped rescue Alcántara.

This will always be the fate of some prospects, even those identified as good players by baseball minds as perceptive as those that run the Cubs. Under Epstein and Hoyer, the Cubs have largely been shielded from the failure of any one prospect, as they’ve been able to acquire bushels of young talent. The team’s margin for error is about to become much thinner, though, as Major League Baseball punishes the Cubs for their successes by handing them less valuable draft picks and a smaller pool of money to sign international players.

The Cubs’ strategy under Epstein has been predicated on building via the high draft picks that go to the teams with the league’s worst records. (The Cubs lost 87 or more games every season between 2010 and 2014.) While most clubs jump on pitching early in the draft, Epstein has not tabbed a pitcher in the first round during his tenure in Chicago. “We can get anybody to pitch,” Verducci quotes Epstein as saying, and, at least for 2016, he was right: Verducci notes the Cubs used 11 pitchers in the World Series, every one of them acquired from outside the organization. But that strategy was abetted by the fact that the Cubs nabbed power hitters such as Bryant and Kyle Schwarber at the top of the draft. The odds that the same caliber of players will be around at No. 27 (where the Cubs are picking this June) aren’t nearly as good, and the Cubs’ chances of continuing to have William Tell–level accuracy both in the draft and with veteran pitching acquisitions are slim.

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A diminished talent pipeline will put additional pressure on another tenet of the Cubs’ philosophy. “Epstein looked for an edge over the rest of baseball,” Verducci writes, “in the character of his players.” Hooray for good intentions. The Cubs temporized on character in 2016 when they acquired Aroldis Chapman, who had been suspended for 30 games under the sport’s domestic violence policy during his tenure with the New York Yankees. This was a betrayal of the franchise’s stated values, expedient because of Chapman’s status as one of the best relievers in major-league history. Talent has superseded moral posturing going back to the earliest days of professional baseball, and it always will.

While the Cubs are better or smarter than other teams in some areas, when it comes to bottom-line considerations, they are just like the rest, with all of the attendant vulnerabilities and possibilities for error. The front office’s greatest miss is perhaps the best indicator of how the Cubs might hurt themselves going forward. The complete destruction of Jason Heyward’s hitting mechanics is barely discussed in The Cubs Way except as a counterpoint to Heyward’s own big character moment, which came when he rallied the team during the rain delay near the end of Game 7 of the World Series. An outstanding defensive outfielder whose bat was always a little light for an outfield corner, Heyward reached free agency at the unusually young age of 25. In December 2015, the Cubs signed him to an eight-year, $184 million contract.

Right move, right player, wrong outcome: Heyward batted .230 with an on-base percentage of .305 and a .325 slugging percentage in the regular season, and he was so lost in October (he went 5 for 48) that Maddon benched him. At present, he’s reworking his swing. While spring training statistics should be taken with a shovel full of salt, the early results are not promising. Regardless, Heyward will be part of the Cubs’ picture through 2023, either on the field, on the bench, or as a vampire sucking salary from the team budget. This can and will happen again.

Entropy is already pulling at the Cubs in other ways. Center field Dexter Fowler is gone, and his replacements, Albert Almora and Jon Jay, are almost certain not to perform at the same level that Fowler did last season. (To be clear, neither was Fowler—that’s why this stuff is hard.) Serviceable fifth starter Jason Hammel finished the season in a tailspin and has departed for Kansas City. His spot is being taken by a combination of left-handers Mike Montgomery and Brett Anderson, the first of whom has yet to succeed as a starter while the second has stayed healthy through a full campaign just twice in the last eight years. Starting pitchers Lester, Arrieta, and John Lackey are a year further into their 30s, and the latter two are unsigned after this season, as is closer Wade Davis. He replaces Chapman, who has returned to the Yankees, grumbling about the way Maddon rode him in the playoffs. So much for team above self. Due to the club’s hitting-first drafting strategy, high-value replacements aren’t necessarily on hand if these pitchers leave or age out of usefulness.

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Most dangerous of all to the Cubs is the affection management and players feel for each other, a heartwarming aspect of the team that is contraindicated when it comes to sustaining a winning run. They love Rizzo. They love Schwarber. Epstein says of Bryant, “If we have daughters, that’s the guy we’d like her to marry.” Although Washington Senators owner Clark Griffith traded Joe Cronin, a future Hall of Fame shortstop who was married to his daughter, more often than not sentimentality gets in the way of a successful baseball operation. Are you going to be willing to trade your best pal (or your son-in-law) if he’s hitting .220?

As general manager of the Red Sox, Epstein had the audacity to trade Nomar Garciaparra in the midst of the 2004 pennant race. If he retains that same level of ruthlessness, then sentimentality won’t be a huge problem for the Cubs. The four other teams in the National League Central also don’t seem likely to give Chicago a strong run for the division title in 2017, so a postseason encore is likely this year. After that, the centrifugal force will become even stronger as the team’s young players ride the salary escalator upward. Some of those youngsters may fail—as good as Javier Baez is on defense, if he remains a .231/.268/.367 hitter against right-handers, the Cubs will eventually move on—as will seemingly “safe” veterans, such as Heyward, who will fall off a cliff for some unforeseen reason.

At that point, the only thing that will keep the Cubs on top will be the kind of ruthless self-assessment that led to them shelving their values and acquiring Chapman. One lesson to draw from the Cubs’ way (as opposed to The Cubs Way) is that to succeed against tough competition, you have to be willing to shelve your ideology.