An epic 2016 World Series ended with one of the most memorable games in recent baseball history. The Chicago Cubs ended their 108-year championship drought with an 8-7, 10-inning win over the Cleveland Indians in Game 7.

While the elation is through the roof in Chicago, the disappointment is deep in Cleveland. Both teams, however, have plenty to address this offseason to ensure they make it back to the Fall Classic. Each club is facing important departures and obstacles that could affect the chances of a rematch in 2017.

Let us take a look at two major questions facing the Cubs and Indians, respectively, as they head into a significant offseason.

    

Can Chicago Re-Sign or Replace Pending Free Agents?

The Cubs went wire-to-wire as the best team in baseball, thanks to a loaded lineup and deep pitching staff that resulted in the seventh-highest payroll in the sport. Yet, the club may be forced to part with several key pieces of its championship squad.

Chicago has four significant players who could become free agents this winter in Aroldis Chapman, Chris Coghlan, Dexter Fowler and Jason Hammel. How the team handles these situations could have a tremendous impact on next season.

Fowler signed a one-year deal worth $9 million last offseason with an option to initiate a $5 million buyout to decline the second year, per Mark Gonzales of the Chicago Tribune. The 30-year-old could decide to opt out after he posted a .276 average with 13 homers and 48 RBI this season,. Those were his best numbers since 2012. Fowler was also a hero in Game 7, going 3-for-5 with an RBI, thanks to a historic swing, per Bleacher Report:

Perhaps more important to Chicago’s postseason run was Chapman, a trade-deadline acquisition who solidified the team’s pitching staff. Since Chapman’s arrival from the Yankees, the Cubs converted 16 of his 18 save attempts with a 1.55 ERA in the regular season. He also became the only bullpen member manager Joe Maddon trusted near the end of the World Series. Chapman pitched 5.1 innings with 97 pitches thrown in the last three games.

Coghlan and Hammel are less significant, as the former served as a reserve outfielder this season while Hammel won 15 games before failing to make the postseason roster. Given the value of starting pitching in MLB, it is hard to imagine Chicago making any legitimate effort to keep Hammel signed, as he could command some solid money.

The same could go for Fowler, as he could be in for a payday after his strong playoff finish. His .276 average was the second-highest of his career. As such, Chicago could be better suited to keep Coghlan in the outfield rotation. The Cubs then could promote a younger guy such as Javier Baez or Addison Russell to replace Fowler at the top of the order.  

This would end up saving the Cubs a long-term deal that could top $10 million a year for Fowler.

Lastly, Chicago should try to retain Chapman, but it has to be smart. The 28-year-old could command one of the biggest contracts ever for a reliever. Meanwhile, the Cubs have young players such as Baez, Kris Bryant, Russell and Kyle Schwarber who will eventually require hefty new deals.

For the right price, Chapman would be a perfect fit for a Cubs team that needs bullpen help. But that cost could end up being too high, as John Harper of the New York Daily News expects the Yankees to make a serious run at the closer.

    

Should Cleveland Bring Back Mike Napoli?

After outfielder Michael Brantley’s season ended due to a shoulder injury early in the season, it seemed Cleveland would have a massive hole in the middle of its lineup. Luckily, first baseman Mike Napoli came through for the Indians.

In 2016, Napoli experienced a career renaissance with his power at the plate, which Cleveland desperately needed. Even with Napoli‘s 34 dingers, the Indians still finished 18th in homers in the majors. However, the 35-year-old is a pending free agent, and it is not clear how the team will handle this situation.

Prior to Game 6, ESPN’s Jerry Crasnick reported that the Indians have interest in bringing back Napoli, and the team believes the player shares that intrigue. 

“We have a desire to have him here, and my sense is that he has a desire to be here,” said Cleveland general manager Mike Chernoff, per Crasnick. “That’s something we’ll have to address once the World Series is over.”

Napoli will likely expect a raise from the one-year, $7 million deal he played on last season, given his production. But is this something Cleveland should want? Napoli is not a young player, and this past season was an outlier compared to his previous five campaigns:

His postseason numbers were also dreadful. Napoli posted a .173 average, one homer, three RBI, 21 strikeouts and just four walks. During Game 6, Sports Illustrated‘s Jonah Keri noted that Napoli‘s production was even worse, considering where he was hitting in the lineup:

The Indians do not have the payroll of big clubs such as the Cubs or Yankees. It cannot afford to be risky with players battling inconsistency such as Napoli. With Brantley set to return and the team having the option to re-sign Carlos Santana, Cleveland can make up for Napoli‘s production. It should move on unless he decides to stay at a discounted rate.

    

Can Both Teams Return to the World Series?

Chicago was the best team in baseball this season, and it could be better in the coming years. The team could even challenge this historic mark, courtesy of MLB.com:

Cubs President Theo Epstein has done a magical job of creating an influx of young talent, which sets the team up for a potential dynasty. Anthony Rizzo is the oldest member of Chicago’s offensive core moving forward at 27 years old. The remaining position players are all 24 years of age or younger. For being so young, this group still put up impressive numbers this season:

Other than Rizzo, the guys above—as well as Schwarber—have not even hit the peak of their primes yet. When they do, this lineup will be downright scary.

The rotation is also in good hands, as its top three arms still have plenty in the tank to propel another championship run. Jake Arrieta is 30 years old; Jon Lester is still 32. And 26-year-old Kyle Hendricks led the majors with a 2.13 ERA in the regular season and added a sparkling 1.42 mark in the postseason.

All three players are locked up until at least 2018, which makes the top of this Cubs rotation arguably the best in baseball next season. The bullpen could use some work, but this unit cannot be fully evaluated until the Chapman issue is resolved.

Cleveland also has plenty of reason for optimism because of the boost it will receive next season from players returning from injury.

Not only will Brantley return next season, but the New York Post‘s Joel Sherman reports that the star could be available for the entire season.

“He should be fine for spring training next year,” Chernoff said, per Sherman.

The Indians could deploy him with emerging superstar Francisco Lindor to solidify a lineup that still ranked fifth in MLB in runs without Brantley.

Cleveland was able to make this postseason run without several other key parts, as Tom Withers of the Associated Press noted:

Those two pitchers are Carlos Carrasco and Danny Salazar. The latter returned for some relief work in the World Series, while Carrasco was shelved for the entirety of the playoffs. Here is what the Indians were missing behind ace Corey Kluber:

Having these two dynamic arms could have made the difference in this series for Cleveland. Yet, their absences gave 25-year-old Trevor Bauer some valuable experience. Bauer’s development in his fourth full season could give the Indians a formidable rotation of their own.

Napoli and possibly Rajai Davis are the only impactful free agents with a chance of leaving. Cleveland will return its sensational bullpen of Cody Allen, Andrew Miller and Bryan Shaw to go with its returning healthy players.

Given what each team is bringing back, Chicago and Cleveland look to be the favorites to emerge from their respective leagues. The volatility of MLB makes it unlikely that this will happen, but there is a chance the world could be treated to a sequel of this memorable matchup.

    

Statistics are courtesy of MLB.com unless otherwise noted.

Contract and free-agency information are courtesy of Spotrac.com. 

Read more MLB news on BleacherReport.com