The Chicago Cubs won 95 games this season, but fans and writers alike are more focused on the games that they lost as the 2018 campaign came to a crashing end.

The Cubs’ offense struggled at times in 2018, getting held to one or fewer runs in a staggering 40 games, and their starting pitching dealt with a variety of issues, with Yu Darvish and Tyler Chatwood both battling ineffective stretches and injuries while Jon Lester showed some signs of slowing down in the form of increased walk rates and decreased strikeout rates.

What will Theo Epstein and Jed Hoyer do to bring the Cubs back to World Series contention status? Which players could be dealt and which ones will be kept?

Here are the five biggest questions facing the Cubs as the offseason begins.

How Much Longer Will Joe Maddon be in Chicago?

Epstein confirmed this week that Maddon will be at the helm for the Cubs in 2019, but his future beyond that remains up in the air, as his contract will expire following next season.

The most likely scenario seemingly is for Maddon to agree to a two-to-three year contract extension, giving him some financial security and giving the Cubs some flexibility on the back end of the deal if they decide to make a change, or if Maddon decides to retire.

What Will the Cubs Do About Addison Russell?

Russell, who missed the last weeks of the season under a cloud of domestic violence allegations, will miss the first 40 games of the 2019 season as part of his punishment in MLB’s investigation, but when he returns to the diamond, will he be wearing a Cubs uniform?

The Cubs already have a dynamic shortstop option in Javier Baez, and free agents like Manny Machado and DJ LeMahieu could be on their radar if they decide to bolster their middle infield spot and let Russell go.

Cole Hamels, Daniel Murphy Highlight Potential Cubs Free Agents

How About That Contract Option for Cole Hamels?

The Cubs are in a bit of an interesting spot with Hamels, as they currently hold an option on his contract for next season.

In 12 starts with the Cubs, Hamels posted a 4-3 record and a 2.36 ERA, and struck out 74 batters in 76.1 innings of work this season.

If the Cubs do decide to pick up his $20 million option, they will be on the hook for the entire thing, according to multiple reports. If instead they choose to let him become a free agent, the Rangers would pay the $6 million buyout on the deal.

Will the Team Trade an Outfielder to Add More Arms?

The Cubs have a glut of outfielders, with Albert Almora Jr., Ian Happ, and Kyle Schwarber all competing for playing time. Add Ben Zobrist and Kris Bryant into that mix, and things can get downright complicated for Chicago.

Obviously having more players than spots isn’t necessarily a bad thing, but with the talent that players like Happ and Schwarber bring to the mix, a trade for help in their bullpen or pitching rotation could be on the table, especially with Bryce Harper available on the free agent market.

Will the Cubs Target a Top Free Agent Again?

Speaking of Harper, this is the single biggest question facing the Cubs. They have plenty of money to spend, as the team’s renovations of Wrigley Field and tremendous playoff success in recent years have caused the dollars to pour into their coffers, but after striking out on free agents like Darvish, Heyward, and Chatwood, will the team be more gun-shy this time around?