Awful. The best way to ensure that the Cubs win a WS, and hopefully several WS, is to get to the playoffs as many times as possible. That's the only way you can mitigate small sample size variance that inevitably bites you in the ass at times. The Cubs are not going to sacrifice foundational pieces to "go for it" in a single year. Epstein & Co. have been crystal clear in that.
You cannot ensure a single World Series let alone several. You have to treat each year differently. Each year is different with injuries and performances. If you are missing a key piece, you go get it. Giving up Schwarber would have no impact on this team whatsoever, a team that can win it all this year with the hitting it has. The #1 goal of every year is to win the Championship. Being close does not matter unless you are a fan of the Cubs slogan of "Wait til next year."
That bolded part is where you really lose me. This team has been built to win for several years how does the past predict the future? Because other Cubs teams haven't been built for the long term? To me this is a silly as the bit about "they have to win this year because it's been 108 years". I'm not interested in a one year juggernaut I want multiple opportunities to root for a playoff team with legitimate WS chances. The playoffs are a crapshoot the key is to win your division so you don't have to go through the WC game. After that it's about who's hot, who's not and match ups. Going forward this team does need pitching because the best pitching prospects are 2-3 years away so even if you do consider trading Schwarber why trade him at his lowest value for a a relief pitcher when a healthy left handed hitter of that caliber is the kind of thing you need to trade for TOR starting pitching? Andrew Miller is an excellent relief pitcher but does this team need that or just a very good LOOGY of which there are other options that won't cost a potential top 10 MLB bat. We've all waited our lifetimes for an organization this good, with this much talent and the idea of trading for a pen arm with a guy at his lowest value makes ZERO sense to me.
The Chicago Cubs have been the laughingstock of all of baseball and sports as a whole for many decades. They are known as chokers and the Lovable Losers. That is a stigma on the whole organization whether the current players buy into or not. If they choke it away this year, they will be the brunt of so many more jokes as there are expectations on them now.
You have no guarantees going forward. Try to win this year. Giving up a good hitter who is terrible in the field for a top end left handed relief pitcher is a trade from our strength to fill our weakness. We don't need Schwarber this year or any other year. This team will be good for many years and the current hitters will get better yet. Pitching is a differentiator. Look at KC last year and how great their pen was along with the rental of Cueto. They went for it and they have a championship that nobody can take away from them.
I love how Bowman makes moves EVERY year at the deadline. Nothing major but he acquires key pieces focusing on that year because that is where the focus should be. His approach has led to championships yet they are competitive every year due to how the organization is run as a whole. The Hawks are looked highly upon in sports. The Cubs will be the laughingstock of all sports until they win a World Series. To not think that 108 year stretch comes into play in naïve. I believe Theo has a sack.