CHICAGO -- Though they've won the most regular-season games in baseball over the past four seasons, the Chicago Cubs aren't likely to catch much of a break from fans this weekend during their annual winter convention.

Coming off a disappointing finish to 2018, combined with little to no action during this offseason -- while navigating the possible return of maligned and suspended shortstop Addison Russell -- Cubs brass are likely to face tougher questioning than they've had in years.

Front and center will be manager Joe Maddon, who's entering the final year of his contract -- though you wouldn't know it from talking with him. In fact, without any assurances about his future after 2019, he's still planning on opening a restaurant in Chicago -- Maddon's Post is the working name -- all while making sure the Cubs return to postseason prominence.

"I came up on one-year deals, but you always felt if you worked well and did your job that stuff will take care of itself," Maddon said Tuesday night at a charity function in Chicago to benefit his Respect 90 Foundation as well as the Union League Boys & Girls Club. "For me that hasn't changed. I still believe in those principles."

Maddon has left no stone unturned for the challenge ahead. At the winter meetings in December, he revealed he was reading a book to better understand his players, "Managing Millennials for Dummies." So what has he learned?

"They like change and they work well in groups," he said. "It's about listening to my guys. Sometimes you listen but you don't hear or you hear but don't listen. You have to be careful not to let things slide when people are reaching out to you."

It's hard to know how it all applies to baseball players, but later in the evening, as Maddon spoke to a roomful of fans during a fireside chat with Cubs broadcaster Jim Deshaies, he said most of the book can be boiled down to common sense. Of course, there are differences in every generation, which was noted in the book.

"The millennial group is very technology oriented," Maddon stated. "The answer is at everybody's fingertips."

The Cubs could use some answers on the field as all parties involved seemingly still have a bad taste in their mouths regarding the end to last season, when the team simply stopped hitting. September felt like a death march to an earlier-than-expected vacation, as the Cubs didn't play more than a few days into October.

"This extra month [of time off] is absurd," Maddon said. "When you get an extra month you feel like you've been off for a year."

The extra time for the front office hasn't materialized into anything (yet) for the roster, other than the addition of super utility guy Daniel Descalso. It hasn't been the sort of impactful offseason fans were expecting, especially with Kris Bryant's friend Bryce Harper available.

"Not happening," Maddon quickly said on Tuesday about the former MVP.

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There's still some time between the fan convention and spring training, but it's looking and feeling more and more like the Cubs will have a similar-looking team to last season's squad, which looked a lot like the 2017 edition as well as their World Series-winning team of 2016. Is that so bad? Maddon made the point of reminding everyone about that win total over the past four years, then went ahead and made the case for his current crop of players.

"We feel like as though we have all the ingredients in the bowl," Maddon said. "It's already there and to just go out and purchase guys because some kids had a tough year last year, probably not good form. I'm all about development. I'm with the guys, Theo and Jed, regarding definitely trying to extrapolate more out of the group we already have because there's a lot more left."

There's no reason not to think Maddon believes that, but at the same time what else would he say -- knowing the Cubs' budget did not allow for major additions this winter. "To purchase players, you may not get better than what you have," Maddon said.

Does anyone think that would be his stance if Harper were indeed joining the Cubs to replace Jason Heyward in right field? Of course not. But he's dealing with the hand that he has been dealt -- and trying to make the best of it.

"Just getting guys [physically] well," Maddon said, referencing third baseman Bryant. "If we get Tyler Chatwood [mentally] well, that's a big acquisition. Having Brandon Morrow for an entire season is a great acquisition. And beyond that, a lot of the young hitters. We're looking for that maturation point."

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Some of that might be wishful thinking as Morrow already has been declared out for April as he recovers from an elbow ailment. But the fact does remain the Cubs won 95 games in 2018 with plenty of injuries and underachieving players. The final outcome, a division tiebreaker loss followed by a wild-card defeat, is one reason Maddon didn't receive an extension on his original five-year deal signed before 2015. And it's one reason, especially with a brand-new coaching staff essentially for a third straight season, the 65-year-old manager is going to be more hands-on.

"A lot of it will look the same on the surface but I'll try to get more involved in the background," Maddon said. "Bimonthly meetings [with coaches]. Go over the players. Have everyone on the same page."

In other words, continue to leave no stone unturned. In terms of potentially his last season in a Cubs uniform, Maddon admitted it could affect his life off the field more than anywhere. After all, can he plan a charity event like Tuesday's dinner for his Respect 90 Foundation for 2020? Not exactly. But that's not fazing him either.

"Respect 90 is going to be Respect 90 wherever it is," he said. "We'll see."