With the calendar flipped to 2020, the upcoming baseball season is not far away. Spring Training starts in a little over a month and Opening Day is right around the corner in late March.

If you live in Chicago or you root for one of the two Chicago baseball teams you have seen two wildly different approaches to this winter. While the White Sox have had perhaps the best offseason of any team in the sport, the Cubs have regressed dramatically from their 84-win 2019 team that finished third in the NL Central division.

There is no question the Cubs had a wildly successful four-year run after being built from the ground up by Theo Epstein and Jed Hoyer. They won 97, 103, 92 and 95 games and reached the National League Championship Series three consecutive years, including the greatest season in Chicago Cubs history when the club won the 2016 World Series, its first title in 108 years.

However, for as successful as the Epstein led front office was in building the championship team they have had a very subpar run since that magical night in Cleveland in 2016.

Now, with less than 40 days left before players return to their respective spring training camps there is serious concern the Cubs' championship window has slammed shut.

Currently, the Cubs have a player payroll that is projected to be over the luxury tax and has hampered their efforts to improve a club with several major holes.

Despite losing Cole Hamels ($20 million), Ben Zobrist ($14 million), Steve Cishek ($6.5 million), Pedro Strop ($6.5 million), Brian Duensing ($3 million), Tony Barnette, Xavier Cedeno, and various other salary commitments the Cubs currently have a projected 2020 payroll of $218 million. This includes projected arbitration awards to Kris Bryant, Javier Baez and Willson Contreras, plus salary raises to others such as Anthony Rizzo, Kyle Hendricks and Craig Kimbrel.

How can the Cubs be over the luxury tax after saying goodbye to over $60 million in 2019 payroll obligations?

So, let’s put the cards on the table.

The 2020 Cubs have lost significant talent from their 84-win 2019 team and have done almost nothing to replace ANY of those players. They still have no payroll flexibility to add even mediocre free agents to augment their roster.

So, how did the Cubs get in this position?

To answer that question, I called a former MLB general manager and other high ranking baseball executives, and all spoke with tremendous candor.

Kris Bryant's pending service time grievance has hampered the Cubs ability to trade the former MVP. Consequently, it's hindered their ability to accomplish much this offseason. People around baseball believe the Cubs trade demands are far out of line with what Bryant’s value is in the marketplace.

“The Cubs' asking price for Bryant is a joke," a former GM said. "They want nearly ready major league talent at the level of a Gleyber Torres type or close and there is no chance a team is going to give them a package of those caliber of players.

"I like Bryant but he is not a Top 30 player in baseball in my opinion. He is mediocre at best as a defender at third base. His swing has changed dramatically since 2016 and I question if he is truly 100% healthy. Sure, he has ability and he is a big, strong man but his offensive impact is nowhere close to what he looked like when the Cubs won the World Series."

Multiple people in baseball echoed that sentiment. They don’t see the same impactful offensive player Bryant was in 2015 and 2016, and they believe that the Cubs are in a very difficult spot to turn the team around.

“The Cubs are in a trick box. They did a terrible job locking up their young stars to deals that would have extended their window of contention," one executive said. "Yes, they got Rizzo and Starlin Castro but until Kyle Hendricks took a deal they had signed no one else long term from their core guys. Look across your city and see what Rick Hahn has been able to accomplish. He has a great young core and he has been able to sign some of his guys to outstanding deals.

“The Cubs are trying to jump start their team again and while I don’t blame them for asking for a ton in return for Bryant, I don’t believe they are going to get it."

Another believes the Cubs are in a terrible position as they launch a new TV network. Marquee Sports was supposed to infuse the franchise with a significant revenue stream to allow them to compete with all of the other financial behemoths in the industry.

“If they simply want to move Bryant’s financial commitment for the next two years and get back some decent players then teams will be interested," an executive said. "But when you factor in what they want, what he will be owed (approximately $45 million over the next two seasons) and the fact that he has regressed as a player then they are in a really difficult position.

"I like Bryant but he is not a player that I would pay $30-plus million a year for. He and Scott Boras are going to want a massive deal and I would never commit to that type of commitment at this point in time."

The Cubs have other desirable young stars they could entertain trading for financial flexibility, like Baez and Contreras.

"It is getting late in the offseason and Contreras will not bring you the return that they are asking for and what they are asking for is obscene," the same executive said. "Yes, he’s a really good player but the Cubs want a king’s ransom for him and I don’t see them getting that back.

"As for Baez, he is a great talent but he is their most marketable player and I would be stunned if they traded the number one guy they have that connects with the kids in their huge fan base. Can you imagine, with all of the bad press they have been getting over the past 18 months if they traded their number one asset in Baez? No way they are doing that."

So, as we sit here in early January 2020 the Cubs are eerily quiet as they wait for a decision on Bryant’s service time grievance and the rest of the industry keeps making moves.

"The Cubs did a really bad job developing minor league talent and along with a few bad signings and trades, have really crushed them," one exec said.

"However, if there is one guy I would trust to figure a way out it is Theo Epstein. He will be in the Hall of Fame someday and while I don’t think he will still be there in Chicago in three years, there is no way when his time is up there that he wants to leave Chicago like this."