Cubs: A retool scenario does not necessarily mean they will be focusing on winning down the road instead of sooner, but changes are still significant.
If there was a vague definition for a typical retool in sports, it is making a number of roster changes while keeping some of the core intact. This usually indicates that there is enough on the team at the moment to keep around for long-term success, but big changes will be needed to be made around those select players/coaches. A retool also allows to fix a roster fairly fast, not needing years of development to be contenders again.
Remember the 2016 New York Yankees? Like the current Cubs, they had talent enough to be competitive, however they were clearly not a World Series contender. GM Brian Cashman made several trades that year including Aroldis Chapman, Andrew Miller and Carlos Beltran to restock assets without tearing the entire team down. Since that season they have not missed the postseason.
If the Cubs went this route, then we could see several core players traded away to restock assets while keeping other key players. Just as an example, say the Cubs keep Anthony Rizzo, Javier Baez, Ian Happ and Kyle Hendricks while trading away Kris Bryant, Kyle Schwarber and Willson Contreras. That keeps a chunk of the core team together while exchanging other pieces to restock assets, which could include both prospects and MLB players.
Why the Cubs could go this route:
There is still enough talent on this team to at least compete, clearly as they won the NL Central in 2020. Changes are still needed to be legit contenders. The Cubs won’t spend money, so trades and development is really the only option to improve. With the financial losses of 2020, selling a full rebuild and losing might be tough for the organization to do.
A retool can at least keep them competitive short-term and even in the mix, which will keep fans watching, and the team’s long term outlook can look brighter. Overall it is a quicker and less painful approach, but also risks putting stock into something that might not improve enough.