Besides winning
the 2016 World Series the best moment for Cubs fans was signing Theo
Epstein. He is a revered leader of a franchise and seemed like
finally the right kind of management that could lead the Cubs to the
level they had been waiting over 100 years for. The brain trust of
Epstein, Jed Hoyer and Jason McLeod tore it down and built a World
Series winner, but that window seems shut.

Epstein broke
the curse of the Great Bambino and Boston, he had broken a drought
already, but let’s not forget Boston was happy to see him go. Epstein
had built a World Series winner in Boston, and won two, but was also
the reason the team got stuck in payroll purgatory. Carl Crawford,
Mike Cameron, Julio Lugo; plenty of contracts Epstein handed out
tanked the two time winners. Sounding familiar Cubs fans?

drafted a lot of players to help those Boston Red Sox win but then
depleted the farm system and cap space by making big moves to keep
the contention going, instead it shut the window. The brain trust
made the Cubs one of the best  with top draft picks and shipping out
everyone from the previous regime, but where has that been since they
won the World Series?

Coming in to
the 2020 season the Cubs farm system rated as 23rd out of
30 teams in all of baseball. Their highest rated prospect in the top
100 is number 63 Brailyn Marquez, who’s with the major league club.
They have two other prospects in the top 100, OF Brennen Davis who’s
at A ball and C Miguel Amaya who’s also with the big club. Chicago’s
top 10 prospects has three with the parent club and the rest at A
ball or lower. For the rest of the top 30, three pitchers are in the
majors and every other prospect is A ball or lower. The farm system
is weak.

When you’re
competing you’re going to value production for the parent club, but
Epstein is always talking about parallel fronts, but it isn’t
happening. After that big wave that included Kris Bryant, Javier
Baez, Kyle Schwarber and others, they haven’t been able to replenish
it even in to the middle rankings of the majors. Epstein and his
brain trust regularly draft position players early, where has the
pitching been?

biggest shortcoming, and the biggest contributor, to the down fall of
the Cubs will be his inability to develop pitchers. While the top
ranked prospects that are with the club are mostly pitchers, are they
any top end starters? Jon Lester, Yu Darvish, Jose Quintana, most of
the rotation has been bought and that has left ownership saying ‘We
don’t have any money to spend.’

It has been
the exact same with closers. Aroldis Chapman, Greg Holland, Craig
Kimbrel, all closers either bought or traded for. Now, let’s be
honest the Chapman trade was inevitable. While it hurts to see
Gleyber Torres develop for the Yankees, especially with Chapman
signing right back with the Yankees, that’s the price for the World
Series. However, the White Sox got in to the playoffs in big part
because of Eloy Jimenez. The trade for Jose Quintana was a big set
back from the Cubs and an indictment the organizations failure to
find in house pitching.

Epstein is
entering the last year of his deal and there are already rumors he’ll
stay a lame duck and just walk away. It’s hard to envision after 2016
that just four years later we’d get to 2020 and be okay with Epstein
walking away. For Chicago that’s probably just, and should be, the
beginning of a lot of changes for this Cubs team.

already tried spending to extend the window and it has just seen
disappointing season after disappointing season. The window is
closed. It’s time to blow it up and start fresh. For the first time
in a few seasons the Cubs will have some payroll open up with Lester
a free agent, 25 million team option, Quintana’s 10.5 comes off the
books, Tyler Chatwoods 13 expires. That leaves the Cubs with 87
million, though Kris Bryant, Kyle Schwarber and Javier Baez enter
their final years of arbitration with seven other players on the big
league squad in arbitration.

Anthony Rizzo
has one more team option at 16.5 million that will likely be picked
up. I’d imagine Lester will not have his option picked up but could
be back at a cheaper price. The talent is there, but it’s been well
documented the issues management has had trying to get a deal
hammered out with Baez and Bryant. Again, who would of thought after
2016 those two wouldn’t be sure bets to get another Cubs contract,
but they may have played their last games at the friendly confines.

It was
shortened season for 2020 but Baez still only hit 203 with eight home
runs and 24 RBI. There’s no doubt he has the ‘It factor’ on defense,
but where has the offense been in the post season? Kris Bryant hit
206 in 2020 with only four homers and 11 RBI and has struggled to
stay healthy since winning the MVP. Both are going to expect huge
contracts but have been the core of a team that has regularly
disappointed. Rumors came out of last season’s off season that
whoever would sign the Cubs would keep and they’d move the other, but
now both could be gone.

Expect the
rumors to ramp up this winter as both still aren’t signed and, while
they’re value is depressed now and could keep them on the roster to
start 2021, it doesn’t seem Chicago will pay them as they blow it up
and restock the farm system. Anthony Rizzo could join them on the way
out despite being the leader of this team. Rizzo is 30, hit 222 with
eleven homers and 24 RBI and has not gotten an extension either.

Kyle Scwarber
seemed inevitable to come to a railroad situation at some point as
he’s more suited to be a DH and now enters his last arbitration year.
The theme is reoccurring for 2020 as Schwarbs hit 188 with eleven
dingers and 24 RBI in 2020. His price will be more reasonable for
Chicago, but he was benched during the season for his defense and
needs to be a full time DH.

David Bote and
Nico Hoerner, while not the same caliber as the big stars, provide
solid options at a cheaper rate for the Cubs while they rebuild
another winner. Albert Almora was sent down during the disappointing
2020 season but Ian Happ broke out in a big way. Those three, along
with Wilson Contreras at catcher and Victor Caritini needing a
position, could be the core of the Cubs offense before 2021 is over.

You draft and
trade to develop the type of players the Cubs had, but whatever this
team was going to do looks like it has been done. During interviews
throughout the season the stars knew what this year could mean for
them and they were bad and flamed out in disappointing fashion in the
playoffs yet again. Of course there’s always a risk of never getting
back, but signing the stars means the team won’t change and it could
be continual competitive purgatory.

With the stars
at a depressed value it’s likely they could start the season in
Chicago, but will they finish 2021 in the Windy City? If Epstein
truly is in a lame duck year how does he manage the team? Will Hoyer
take over after he leaves or do they try and win before they possibly
bounce? Running it back would be a mistake and it’s time to to
restart. Very rarely have we seen continued top competitiveness in
the MLB and it looks like the Cubs need to go back to the basement
and figure it out again.