Post-2016, the Cubs have been on a steady decline, Chicago is yet to get past the NLCS since winning the World Series in 2016. It may be time to queue a Cubs rebuild. Hopefully, this time around it will not take 108 years.
Before we dive into potential trades, we must clear one thing up. These trades are based on zero speculations or rumors; these are just scenarios.
Kris Bryant
Kris Bryant may be the most realistic star to be traded from Chicago this offseason. Although many are not ready for Bryant’s departure from the north side, it may be time. There are many different avenues for a Bryant deal. He could fetch a handful of prospects or even a capable, MLB ready player. Let’s look at one potential deal.
One Kris Bryant trade could involve the National League powerhouse Los Angeles Dodgers. The defending World Series Champions could be in the market for a new third baseman if Justin Turner decides to go elsewhere in free agency. Now, despite Bryant’s struggles over the past couple of years, he is an upgrade from Justin Turner.
For the Dodgers to land Bryant and still be able to compete, their core will need to stay intact. Luckily for Los Angeles, they have a strong prospect pool to pick from. The Dodgers would receive Kris Bryant, while the Cubs would receive two right-handed pitching prospects, Josiah Gray and Mitchell White.
Two pitching prospects would be nice, but the Dodgers would need to give up a touch more to land the former MVP. Someone like pitcher Joe Kelly should get the deal done, giving up Kelly would not be a huge hit to the Dodgers and could be helpful in jump-starting the Cubs bullpen.
That is just one of the options for trading Bryant. For more potential Kris Bryant trades click here.

Willson Contreras
Willson Contreras may be a key part of the Cubs right now, but with one of the Cubs’ top prospects, Miguel Amaya due to crack the roster in the next couple of years now may be the time to sell high on Contreras. Any team looking to push themselves over the edge would be in the running for Contreras, maybe a team such as the Los Angeles Angels. A reunion of Contreras and manager Joe Maddon just makes too much sense to pass up.
A deal between the Cubs and the Angels could change the landscape of the American League West. If the Angels want to make a move now to help get star Mike Trout a chance at his first ring, they may be willing to spend big. Now, this may be a long shot, but if both teams pull the trigger it could speed up both the Cubs’ rebuild and the Angels’ push for a title. The Angels receive Willson Contreras and the Cubs receive Angels top prospect Jo Adell.
This trade makes sense on both sides. Although the Cubs could look elsewhere and get more than one prospect, not much would compare to Adell. On the Angels’ side, they may lose a potential outfielder, but they do in fact fill one of the most important positions with one of the best young catchers in the league. The Angels could then take a run at someone such as George Springer to round out their outfield.

Javier Baez
Most, if not all, Cubs’ fans may have nightmares thinking about Javier Baez in an opposing team’s uniform, but if the Cubs want to have a successful rebuild, they need to sell high when possible. Selling off Baez while he is still under team control is their best option to get value.
Baez would be an upgrade to almost any team, with his ability to play either shortstop or second base. What team should take the jump and trade for Baez? The Minnesota Twins. The Twins are just a couple of pieces shy from being true contenders, adding Baez’ glove and bat could push them over the edge. For the Twins to land the Gold Glove shortstop they would have to pay a hefty price.
That price starting with top prospect shortstop Royce Lewis. In addition to Lewis, the Twins would need to throw in a couple more prospects, maybe right-handed pitcher Jhoan Duran and second baseman Yunior Severino.
Now, this is just an idea, in no way am I saying trade, Baez, so please put your pitchforks away.

Anthony Rizzo
Possibly the heart and soul of the north side, Anthony Rizzo may be the Cubs’ most untouchable player. Although he is a highly consistent fielder and a great locker room member, he does not hold as much value as the players listed above. He would, though, be a great mentor to a young team.
What young team could use a veteran such as Anthony Rizzo? The Toronto Blue Jays come to mind, although the Blue Jays have been experimenting with young phenom Vladimir Guerrero Jr. at first base, they could move him back to third base or even play him as their designated hitter to make space for Rizzo. As stated, Rizzo does not have crazy value, but he does still have value.
To start off, the Jays could send Rizzo’s potential replacement to Chicago, that being Rowdy Tellez. Tellez (alone) for Rizzo just does not make sense for the Cubs and their rebuild. In order to cap it off, the Jays would also have to include a prospect, someone such as right-handed pitcher Adam Kloffenstein should seal a Cubs-Blue Jays swap.

Conclusion
As stated, these are just offseason thoughts, there have been no rumors or facts to back any of these up. The Cubs seem to be in need of a rebuild and one of these star players will be the first domino signaling that. Cubs’ fans hope Chicago exhausts all options before rebuilding, but due to Covid-19 stalling revenue and the Ricketts seeming to pinch pennies, a rebuild seems more likely than a retool.
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