2020: Sadly the Cubs’ Last Dance


Whether or not you’re a basketball fan, do yourself a favor and check out ESPN’s documentary on the Chicago Bulls, entitled The Last Dance. The Emmy Award-winning documentary chronicled the rise and fall of the six-time champion Chicago Bulls dynasty, and their superstar, Michael Jordan. While the Chicago Cubs don’t have anything remotely close to the dynasty that the Bulls had, their built-to-win championship team of 2016 is about to be permanently disassembled. Sadly, this year should become the Cubs’ equivalent of their own Last Dance.

A Handful Remain For the Last Dance From the 2016 World Series Team

After 108 years, the Cubs finally won the World Series again in 2016. This was a team that was built to win for years to come, but instead, they began to deteriorate rapidly, beginning in 2017. As of this time, only a handful of players remain from the championship team.

Infielders Kris Bryant, Anthony Rizzo and Javier Baez are still there for what may e the last dance. Catcher Willson Contreras is still on board, as is David Ross, although obviously he’s not the manager and not a player. Outfielders Jason Heyward and Kyle Scjwarber reman from the World Seris team, as does Albert Almora Jr., although he’s been shipped to the Cubs alternate site in South Bend, Indiana.

The remaining pitchers? To use the word “few” would be a gross understatement. Starters Jon Lester and Kyle Hendricks are still around, and although he’d signed with the Reds this winter, reliever Pedro Strop is back with Chicago on a minor league deal. Strop re-signed with Chicago after being DFA’d by the Reds a couple of weeks ago.

Failure to Re-sign Key Free Agents Contributes to Last Dance

Contributing to what will become Chicago’s last dance, Cubs’ owner, Tom Ricketts, has slammed the checkbook shut. This past winter, the Cubs wouldn’t even pony up a mere $3M to hang onto Brandon Kintzler. Kintzler was by far the best reliever in the Cubs’ bullpen last year.

They let Nicholas Castellanos walk as well, that coming on the heels of what was called a “deal in kind.” In that scenario, Castellanos wanted to stay in Chicago, the Cubs wanted to keep him, so a handshake deal was put in place until the details could be worked out. In the end, Castellanos would be the last of the big-name free agents to sign. The Reds ended up taking him, as the Cubs couldn’t come close to matching the money Castellanos wanted.

The Final Song in the Last Dance

Now in the last week of the regular season, the 2020 Cubs are in great shape. With now just six games to play, the Cubs hold a 4.5 game lead over both the Cards and Reds, while they’re 5.5 game sup on Milwaukee. The postseason bubble is in reach, though the Cubs have yet to clinch a playoff spot, much less the division. Assuming they do win the division and n appearance in postseason baseball, the road will be steep, as the competition will be insanely tough.

Win or lose, drastic changes will be coming to the Cubs 2021 roster. They’ll lose players to free agency, while others will be traded. The trend will be to secure and or retain younger, cheaper, and most importantly, controllable players.

Free Agents May Dance Their Way From the Cubs

The Cubs are in a position to lose a handful of players to free agency in 2021. I’m not talking about all of the one-year rentals they selected via trade or free agency over the winter, I mean players from the core.


Jon Lester is again, his velocity is way down, and he’s tiring quickly. The Cubs have a team option on Lester for $25M next season, or the choice to buy him out for $10M. Either way, Lester is going to cost Chicago $10M, so the question becomes whether or not Lester is worth an additional $15M for one season. The guy has heart and he grinds away on the mound, but is he worth 25 million as he plays his age 37 season? The short answer would be no.

Lester knows that his performances and effectiveness have been slipping, as do the Cubs. This season, Lester was dropped from the #1 start position all the way back to #4. After a start last week in Wrigley, Lester himself commented that this may have been his last start at Wrigley Field.

Tyler Chatwood is in the final year of a three-year, $38M dollar deal. Chatty was worthless in 2018, but turned it around in 2019, under new pitching coach, Tommy Hottovy. Chatwood is now on the IL, having made only five starts for the Cubs this season. 2021 ill be his age 31 season, so he may be worth hanging onto, but only if he’s willing to take what will undoubtedly be a cheap offer.

Lefty, Jose Quintana is just what the Cubs needed in 2017, despite having to sell off Dylan Cease and Eloy Jimenez to get him. Quintana has always been what I’ve called “quietly solid,” but over the last two seasons, his performance has slipped. If the Cubs lose Lester, losing Q would be quite a blow to the selection of left-handed starters, in fact, it would completely erase southpaws from the current rotation.

Having been just activated from the IL, Quintana started last night against the Pirates (two innings). Quintana spent the majority of 2020 on the IL after severing his thumb while washing dishes, and most recently, it’s been a lat issue. The Cubs need to get the start out of him, but it may be more about showing potential suitors that he is indeed healthy. Q was only mildly impressive in his three appearances this season (one start, two in relief), despite his 7.50 ERA.

Last Dance for the Cubs’ First Baseman?

Anthony Rizzo finds himself in a similar predicament. After signing an extremely team-friendly deal (eight years/$60.5M), the Cubs hold a team option on him for 2021, as well. It’ll cost the team $16.5M to hang onto Rizzo for the 2021 season, but he’ll become an unrestricted free agent in 2022. Rizzo will be looking for a big contract, and rightfully so, but it’s unlikely the Cubs will offer up Rizzo’s just reward. Rizzo may be worth the money for 2021, but do the Cubs use him for that final year, or trade him before he walks away as a free agent in 2022?

Kris Bryant’s Last Dance

After losing his service time grievance over this oast winter, the Cubs now own Bryant through 2021. I don’t see him staying there. His agent (Scott Boras) will price him right out of the Cubs’ budget, which may not be the worst thing in the world.

Despite being the MVP in 2016, Bryant has fallen from the pedestal since that time and is now batting an abysmal .195. His fielding errors are up, his batting numbers are down, and every other day he seems to incur another injury. Last night he tweaked an oblique during his first at-bat, prompting Ross to pull him and begin using David Bote at third for the remainder of the game.

Not even remotely tongue-in-cheek, Cubs’ announcer likened Bryant’s constant injuries to Gilda Radner’s “Roseanne Rosannadanna” character on Saturday Night Live from the 70s. Her famous quote? “It’s always something.”

The Cubs need to move on from Bryant, so his last dance might be something to behold, even if it is on the IL.

Within just a couple of years, the Cub will also see Javier Baez, Willson Contreras, Kyle Schwarber and others from the core reach free agency, and sadly, they’ll never keep them all.

Winning the World Series would be a great parting gift for this team who never materialized into the dynasty that they were supposed to become. In the meantime, all the can do is try to win the last set of games through October. Meanwhile, they need to dance like nobody’s watching, because this may be their last dance.

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