This is my main issue with the Cubs plan. I didn't agree with the "full rebuild" plan from the start, and after witnessing the plan in action, I think the plan is very weird.
Samardijza really isn't that young, and he's not a top starting pitcher IMO. Castro is a good hit/no field SS who would be a nice #7 or #8 hitter on a contending team. Rizzo is a #6 hitter at the 1B position.
The Cubs make it seem as if the rebuild plan is very detailed and regimented...certain things are going to happen at certain times, like a Step 1 Step 2 Step 3 flow chart. The problem is that Step 1 never took place. Sveum was a disaster as a manager. Castro and Rizzo are peripheral pieces at best. And now the good young players are being kept in the minors simply because its "part of the plan", and the Cubs want to "time" their appearance in the Majors where they are being the final additions to an already competitive team. Its also a money-saving ploy, where the Cubs have these good young players hitting the FA market as late in their careers as possible.
Who would want to be a part of such a terrible organization? If you are a good young player, how could you not realize that you are being kept in the minors while lesser-talented players are on the Cubs major league team simply because the Cubs don't want to pay you? Wouldn't that make you want to leave the organization as soon as you possibly could? And if the Cubs aren't winning World Series while guys like Baez and Bryant are still on their initial contracts, then do the Cubs think they'll have a chance to re-sign any of these guys once those initial contracts expire?
It seems like the Theo plan was supposed to be this well thought-out, multi-year strategy where the Cubs gradually improve into a contending team. I think the reality is that the Cubs will continue to suck and will actually get worse until there is a singular mass influx of minor league talent brought up to the Majors. Its already at the point where the players in the minors are better than the players on the Cubs major league roster...and the only reason the Cubs haven't enacted this singular mass influx of minor league talent is because they don't want to pay them.
Thats my casual fan view of the situation.