“Don’t cry because it’s over, smile because it happened.”

This is the quote that continues to ring inside my head, as the thought of the Chicago Cubs core breaking up, and this historic era coming to an end, seems more like an inevitability than a possibility this offseason. While change can be good and necessary in times like these, it doesn’t make it any easier.

The Chicago Cubs saw their season end abruptly last Friday at the hands of the Miami Marlins, who will be moving on to the Division Series to face the Atlanta Braves. The Cubs got a stellar performance out of Kyle Hendricks in Game 1, but he hung a curveball in the 7th that Corey Dickerson rocketed to left center field, against the wind, for a 3-run home run. The Marlins added a couple insurance runs off reliever Jeremy Jeffress later in the inning, but it didn’t matter. The way the Cubs bats have been silent this season, especially in September and October once again, the game was over when the ball met Dickerson’s bat. Hendrick’s stat line didn’t do justice to his performance as he had gotten out of jams all day long with his varying pitch selection and elite location that has transformed him into one of the most reliable pitchers in baseball the past five years. It’s incredibly hard to pitch knowing that one mistake could be all it takes to lose a ball game. Yu Darvish then came out in Game 2, and as he had all season, pitched brilliantly. He had everything working for him, and often made Marlin’s hitters look lost up at the plate. To be fair, how can you ever be comfortable in the box when Darvish has seven different pitches he can deploy at any given moment? Unfortunately, once again, it didn’t matter. The Cubs couldn’t get any sort of offense going, and thus, their season came to an end.

If this story sounds familiar to you, it’s because it is. The late season offensive collapse, and October ineptitude, has been the story of the Cubs for three seasons in a row. It’s the main reason why now, more than ever, feels like the end of this Cubs era that has brought so much success to this organization, and joy to its fans.

In 2021 Kris Bryant, Javier Baez, Kyle Schwarber, and Anthony Rizzo will be playing on the final year of their contracts. Jon Lester, the catalyst of this Cubs run, may have already pitched his last game at Wrigley Field. His 6-year contract, signed in 2014, has a team option for 2021 at $25 million, but that surely will not be picked up and will be bought out for $10 million. There is still a possibility that Lester returns on a 1-year deal, but it’s likely 50/50 at best given the current state of the team. As for the others, a trade this offseason of at least one of them is likely.

“Clearly, some change is warranted and necessary,” Cubs President, and architect of this core, Theo Epstein said at his end of the year press conference on Monday. “We have not performed up to our expectations offensively – and especially at the most important times in a year – and simply hoping for a better outcome moving forward doesn’t seem like a thoughtful approach.”

“So, embracing some change, even significant change, is warranted. Is it possible to thread the needle and improve in 2021 while also setting ourselves up for the long-term future? I think it is.”

The obvious targets for trade to realize the level of change Epstein alludes to is Bryant, Baez, Schwarber, and Rizzo. Bryant has been the one that has popped up most in trade conversations in the past, and many thought it was something the Cubs might pull the trigger on last offseason, but they didn’t. The reason a trade didn’t happen was because the asking price was incredibly high, and rightfully so. Bryant is a former MVP, Rookie of the Year, and 3-time All-Star. When healthy he is one of the most productive players this league has to offer. When you have a player that good, you don’t usually settle in any trades. You need an MVP type haul in return.

The Cubs clearly need a change though, and as Epstein said, throwing out the same exact team and expecting different results is getting eerily close to the definition of insanity. The issue is that finding the right trade could prove to be extremely difficult. Especially after the down season all these guys just had. This is, of course, aside of the uncertain economic landscape of MLB due to COVID-19. That is whole other obstacle that could cause major issues in and of itself. A topic for another day, perhaps.

Covid issues aside though, trading any one of these guys this winter won’t be as easy as most think. Right now, all these guys have a value lower than it’s ever been in the trade market, especially Bryant and Baez. Due to this fact, it’s murky waters that the Cubs will have to navigate this winter. It’s blatantly obvious that the Cubs need some change in the lineup, but where that change comes from is not clear. The only players currently under contract with the Cubs that hold significant value are Yu Darvish, Kyle Hendricks, and Willson Contreras. Parting with any of those three seems highly unlikely. A year ago, trading Contreras seemed much more plausible than it does now. The Cubs farm system is probably deepest at the catcher’s position with the likes of highly rated prospect Miguel Amaya, and top catcher in last year’s international class, Ronnier Quintero. At this time last year, Victor Caratini looked like he was ready to be a full-time player and could handle the starting duties while serving as a bridge from Contreras to Amaya and Quintero. Contreras also had some glaring weaknesses as far as receiving and pitch framing that made him a net negative player defensively. After this year, neither of those two proved to be true. Caratini regressed tremendously at the plate and struggled all year to make good, hard contact, even though he was able to find some holes. While Contreras miraculously transformed into one of the best defensive catchers in the league. He put a lot of hard work in this past offseason, and it showed. His bat always projects to be above average, and now that his glove does too, he is an extremely valuable asset. Add that in with Caratini’s projections taking a dive, Contreras now appears more likely to receive an extension than be traded. Theo mentioned finding a trade that would improve the team for 2021 and in the future, but the only players that get you an immediate impact player, or an A-level prospects are these three, and I don’t think they are going anywhere.

In prior years, the Cubs most valuable assets were clearly Bryant and Baez. However, both struggled immensely this year. Most reports suggest Bryant is still the most likely to be traded, but I don’t think that trade comes easy. The part that most people don’t understand is that Bryant’s value has literally never been lower than it is at this very moment. The A-level prospects that we were talking last offseason in a trade for Bryant, is just not on the table anymore. The return for him would be B-level prospects at best. Do you really want to trade a former MVP for a B-level prospect? I know I don’t. I would rather ride out a year with Bryant, presuming he is healthy. Then by the trade deadline either the Cubs are in 1st place and they can go for the pennant, or they aren’t, and if Bryant stayed healthy, his value will be higher than it is today. Plenty of teams in a pennant race look to add an impact bat at the deadline, and the return for it is, historically, high. I know in this scenario you’re taking the risk of Bryant getting hurt once again, and then losing him for nothing while simultaneously getting no value out of him on the field in 2021, but it’s certainly going to be an option Epstein and Jed Hoyer discuss. If they couldn’t find the right return package for Bryant last year, I don’t have high hopes they will find it this year either when his value is significantly lower.

It will also be difficult to find the right trade for Baez, for many of the reasons stated above. His trade value is extremely low, comparative to what it has been in past years. Baez was also deep into extension talks with the Cubs last offseason, so they would have to have a complete change of heart to trade him now. Not impossible given the unique circumstances the Cubs find themselves in, but still rather unlikely. Extension wise, his price may have gone down after his abysmal performance this past season. If the Cubs still believe in him, maybe that makes them more likely to find common ground this offseason and sign him to an extension.

Furthermore, there’s almost a zero percent chance the Cubs don’t extend one of Bryant or Baez. They are the teams two best players, and they won’t let them both leave the organization. One of them is getting extended, and for the mere fact that Baez’s price tag looks to be significantly lower than Bryant’s, my money is on him working out a deal with the Cubs. Just like Contreras, I think Baez is more likely to be extended than traded.

That leaves us with Schwarber and Rizzo. Two of the fan favorites of this team for the past 6 years. It’s hard to imagine either of them in different uniforms. Rizzo was upset last season that the Cubs wouldn’t engage with his representatives on a long-term extension, but that is likely attributed to the fact that they really didn’t need to. His team option for 2021 was always going to be picked up. It’s a team friendly option for one of the team’s best players. Also, Rizzo is 31 years old. Usually around this age is when players start to decline a little bit, and he already has well documented back issues that he deals with every year. An extension for Rizzo doesn’t project to be anywhere near those of his contemporaries in Bryant and Baez. It shouldn’t take as long to get a deal worked out. It is my opinion that Rizzo, who has been the heart and soul of the golden era of Chicago Cubs baseball, should spend the rest of his career in this uniform, and retire as a Cub. Now with the DH likely headed for the National League on a permanent basis, this makes even more sense. Rizzo needs a C on his chest, and to be in that dugout until the day comes that he wants to retire. He has earned that, and I look forward to seeing #44 hanging from the foul poles one day.

Schwarber has had obvious flashes of greatness (2015 playoffs, 2016 World Series, 2019 second half), but he has never been able to put it together consistently. He is a much-improved fielder, something he never gets credit for, but his bat just hasn’t been as consistent as everyone projected it to be. It looked like he finally put it all together the second half of 2019, but that didn’t carry over in to 2020. Schwarber is a tough one because left handed power bats are one of the most widely coveted commodities in the league, but he has still underwhelmed. He’s given us so many moments that none of us will ever forget, but I think if any of the core guys get traded this offseason, he is probably the first to go. If Bryant gets traded, which it looks like he will at some point due to how far apart he and the Cubs seem to be in extension talks, it probably happens closer to the deadline. This front office has always held Schwarber in a higher regard than most others in the league, which is why he has never really come close to being traded in the past, even when most thought he was better suited as a DH in the American League. A trade of Schwarber doesn’t get a huge return, but probably nets the Cubs more than the value he currently holds due to the potential so obviously being there. Unfortunately, he hasn’t been able to tap into it consistently, and might never, but some team out there will want to take their shot at helping him realize it. I always hoped it would be in Chicago, but like Bryant and Baez, I think only one of Schwarber and Contreras gets extended, and Contreras is the favorite.

Looking at this piece by piece and considering that many of these players have never had a value lower than they are now, it’s still very possible the Cubs run it back with this same group of guys, once again. It’s more likely that at least one of these guys gets traded this offseason, but it is by no means certain.

Whether a trade happens this offseason, next trade deadline, or they all hit free agency in a year, the end is clearly near. While it’s important to be objective and think about what is best for the future of the organization and analyze the best avenues for sustained success, it is equally important to appreciate these guys for what the have done.

Has this group underwhelmed since 2017? Of course. Has this group underachieved? Not in the slightest. These players achieved feats together that many don’t their whole career, including winning a World Series for the Chicago Cubs. Something that had not been done in 108 years.

Let me say that again… 108 years

My Grandfather, a huge Cubs fan, lived to be 91 years old, and never got to experience the moment that these group of guys gave all of us. Don’t ever forget that. If any of these players leaves town, they should be given a hero’s farewell, because that is what they are. These guys are heroes. They are our heroes…and they always will be.

Do you remember that feeling you had when Kyle Schwarber sent a baseball into Allegheny River off Gerrit Cole in the 2015 Wild Card game? Or what about the one he landed on the video board against the St. Louis Cardinals in the Division Series that very same year? Then, after tearing his ACL at the beginning of the 2016 season, he made the improbable comeback for the World Series, and somehow, was the Cubs best hitter. How was that even possible after missing the whole season? It was unbelievable. That moment will go down in Chicago Cubs folklore forever.

If Javy Baez has played his last game as a Cub, it’s hard to narrow down just two or three moments that put us in awe. He has managed to do it almost every game. His homerun off Johnny Cueto in Game 1 of the 2016 NLDS is certainly one that stands out. With the wind blistering in all night in a game that saw Cueto and Jon Lester matching one another with scoreless inning after scoreless inning, Baez took one deep in the bottom of the 8th that sent Cubs fans everywhere into a frenzy. That kicked off the historic postseason run, which also saw Baez take home the Co-NLCS MVP award with Jon Lester. He was tremendous that series.

Kris Bryant was once the highest rated prospect in baseball. He was tasked with shouldering the hopes and dreams of an organization that hadn’t seen a World Series in 71 years, or a championship in 108 years. Bryant went from College Player of the Year, to Minor League Player of the Year, to Rookie of the Year, and finally to MVP. That is a run seen by no other in the history of baseball. We were all filled with immeasurable excitement the morning we saw he was being called up to the majors in 2015. He was the face of the Cubs curse-breaking aspirations. Yet somehow, he exceeded expectations. Doesn’t it seem like a storybook ending that he was the one to get the final out of that 2016 World Series Game 7? Let us not forget, we don’t even get to that game had Bryant not put this team, this organization, and this city on his back down 3-1 in the series. He hit homers to kick off games 5 and 6 with the season on the line, and all momentum favoring Cleveland. By all accounts, Bryant seems to be just an unbelievably good human too. Kris Bryant’s don’t come around often. Appreciate Kris Bryant.

Finally, that leaves us with Anthony Rizzo. The heart and soul of this era of Chicago Cubs baseball. For the past six seasons, Rizzo has undoubtedly been the leader of this team. Whether it was him ready to brawl with the whole Cincinnati Reds team in 2014 symbolizing that the days as “lovable losers” were over, or when he caught that final out on the ground ball to Bryant in Game 7 of the World Series, he was always the heartbeat of this team. Rizzo seems destined to have his jersey retired and hanging up on one of the foul poles in historic Wrigley Field. How could he not? None of this happens without him.

In fact, none of this happens without any of these guys. Each and every one of them contributed in a major, and irreplaceable way to the success of the past six years. I know that the late season struggles of the past 3 years may leave a bad taste in the mouth of some, but I often wonder if the years were flipped and this era ended with two NLCS trips and a World Series title, would the underachieving narrative still be there? I don’t think so. It’s hard to play the “what if” game, but remember, in 2015 the Cubs weren’t really supposed to be that good yet. They were a team built with the intention of being competitive and taking a step forward to maybe being a .500 team. Instead, all these guys exploded onto the scene to win 97 games, took out two division rivals in the playoffs, and came within three wins of a trip to the World Series. That was completely unexpected, and rightfully changed expectations going forward, but don’t forget where we were before then. It’s fair to criticize them for underperforming in September and October the past 3 years, but it’s also important to recognize what they have still accomplished. In the past 6 years, only two other teams have won more games that the Chicago Cubs, and they are the Los Angeles Dodgers and Houston Astros. Neither of which have a World Series title in that span (at least not one without a giant asterisk).

These group of players brought the fanbase something that was once thought to be impossible. They won a World Series for the Chicago Cubs, and that, more than anything else, will be their lasting legacy.

Before the last out on that rainy night in Cleveland, legendary radio broadcaster Pat Hughes said, “You are going to remember where you were, right now, for the rest of your life.”

I will remember November 2, 2016 until the day I die. That is a feeling that will never be replicated. This group of guys gave us that. I still get emotional watching that final out.

I hope I never lose that.

If this is indeed the end for this group, each and every one of them deserves a tip of the cap, and a thank you.

Thank you for all those moments we will never forget. Thank you for representing Chicago with class, and grace, on the grandest of stages. Thank you for forever changing this organization. Thank you for proving that dreams do not have an expiration date. Thank for you turning “It’s Gonna Happen” into “It Happened”.

Thank you for 2016.

Thank you for everything.

Photo Credit: Matt Slocum/Associated Press

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