How would Cubs approach this offseason if they hadn't won the 2016 World Series?


Look, we're not trying to rewrite history and take a championship AWAY from the Chicago Cubs. 

But it's an interesting thought experiment — how would the Cubs approach this winter if they didn't already have those World Series rings stashed away in their trophy cases or safety deposit boxes?

Would Tom Ricketts and ownership be more likely to throw away the budget and payroll concerns and give Theo Epstein a bunch of blank checks? Would Epstein's front office feel an urgency to wheel and deal or go hard after the top free agents like Bryce Harper? Would they be among the teams most interested in trading for Madison Bumgarner or Edwin Diaz? Would Joe Maddon still be the skipper?

Without that rain delay, if Albert Almora Jr. had not tagged up from first base on a fly ball or if Ben Zobrist's grounder was simply hit right at Jose Ramirez instead of a few feet toward the line, the entire tone and narrative around this winter would be totally different for the Cubs. (To be fair, everything over the last two years would be different in Cub Nation.)

All the talk about the need to weigh production over potential would be full-on shouts if the Cubs were going on 111-plus years of World Series drought.

But, obviously, none of those "ifs" are true. The Cubs did win the World Series in 2016 and the organization certainly doesn't forget that (nor will they ever).

That championship bought Epstein and Co. some well-deserved patience, but it also changed the mentality and expectations, for better or for worse.

"Look, we've won more games than any team in baseball the last four years, we're coming off a 95-win season that ordinarily would leave us in a different mindset just based off the win totals," Epstein said earlier this month. "I don't want to pile on. There are amazing things continuing to happen in this organization, but I think some of it is how to handle success — the greatest quest in sports and accomplishing it at such a young age and it was so sudden.

"...I think there are some things that we can do better in terms of how we approach winning day-to-day, what you need to do from Day 1 through Day 162 and then through October to win. I don't want to get into specifics — and I'm not pointing fingers because I'm intricately involved in this, too — but I know from talking to our players in full candor that we all feel the same way."

Sure, the Cubs shrugged off the World Series hangover enough to make it all the way to the NLCS again in 2017 and woke up on the morning of the final day of the 2018 regular season with the best record in the National League, but any talk of a potential dyansty with this team was clearly premature. 

Like Epstein said, the Cubs have more wins than any other team in baseball since the start of the 2015 season, yet they still have only one ring and now we're on the back half of the projected 7-year window of contention.

The Cubs won't actually trade Kris Bryant right now, but the rumors this winter highlighted an important point — the clock is ticking. Bryant, Anthony Rizzo and Javy Baez all have just three years left in a Cubs uniform while Yu Darvish is the only pitcher under contract beyond 2020 with no clear options in the pipeline (except maybe Adbert Alzolay).

That doesn't mean the sky is falling and the Cubs could obviously still wind up with multiple World Series rings with this core of players. But there's also an urgency now both despite and because of that magical fall of 2016.

"This time is precious," Epstein said. "We're all part of this group that has enough talent to win the World Series and we don't want to waste it. We don't want to look back with any regret that there are things we could've done differently in our preparation or in our work habits or in our attitudes that we brought to the park each day.

"We want to really attack the season with a winning mentality from Day 1 and I'll just leave it at that."

Would the Cubs have lacked a sense of urgency and "edge" in 2018 if they were still on the greatest quest in sports? Probably not, but it's impossible to say. 

The confidence and winning culture the Cubs have developed over the last few seasons worked against them, in a way, in 2018 as they just assumed they'd be OK in the end no matter what kind of adversity popped up along the way. 

And they almost were. It took an incredible surge from the Brewers to catch the Cubs in the division and even took a Game 163 playoff to surpass Baez and Co. 

The Cubs want to get back to that mindset, attitude and approach they had in 2016 — a chip on their shoulder to resolve their unfinished business.

In that prism, being eliminated the way they were might've been the best thing for these Cubs.

"I think everyone in the organization in some form or another expected to be getting back to a fourth straight NLCS," Epstein said, "and no matter what we were up against with the schedule or the injuries or us not hitting for half a season or the Brewers going on an epic run, there was still this belief because — quote — 'We're the Cubs and we have this much talent and we've always come through before, that we'd find a way and we'd look up and we'd be in a fourth straight NLCS.'

"And I think when it doesn't happen and it stops so suddenly and you walk off the field, you have better perspective to evaluate some of the reasons why this time we did not achieve our goal."

That "pissed off" feeling is creating its own sense of urgency this winter — a wake-up call and reminder that this organization cannot rest on its laurels.

But that doesn't mean the Cubs have to feel pressure to overreact this winter. The Cubs have already made some major changes on their coaching staff and there's a legit case to be made that patience is the more prudent path compared to an aggressiveness in regards to potential roster shakeups. There's no longer a dark cloud of "Cubbie Occurrences" or "curses" hanging over this team.

On the one hand, 2016 seems so long ago. But on the other, it is still fresh enough in everybody's mind and there are enough players and coaches and front office members around to help the team duplicate the on-mission environment from Day 1. There's still more than enough talent on this roster to add to the trophy case.

"We didn't really answer the bell the first half of the [2017] season and this past year, there were moments where we were complacent, where we felt we had chances to put away the division," Epstein said. "I think we all felt in the end, we'd be talented enough where it would happen and it didn't. 

"That's on us and we have to own that and we need to change it. That's a real focus for us this winter and it has been and will continue to be as well as player personnel and doing everything we can to find the right mix."

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