There's no reason to be afraid to pull the trigger on a premium upgrade this year. They already kinda went all in on a rent a player in Tucker. You look foolish if you don't do more when you are sitting in the driver's seat in your division, but still being challenged. Especially if Tucker doesn't sign long term.
There is no doubt room to add a SP that can be a playoff starter, because this team is highly likely to be in the playoffs. Everything after that is added bonus. There is enough talent in the minors to make the upgrades to get whoever they want. Ryan and Suarez would be a great trade deadline get. Ryan and Castro or Kelly and Suarez would be great deadline grabs. But I'd be fine with a top line starter and a bench bat that can play 3rd better than either of the two current options. Amaya will be back and contributing soon, too. Assad should be a boost to the pen with a fresh arm. Amaya and Assad will feel like deadline upgrades since we haven't had their production most or all of the year, and are likely improvements over what is already on the roster. Getting Carson more rest will be good for him as well.
Bottom line, they left money on the table preseason. The offer for Bregman should be the bare minimum they have to spend (with less than half a season to play, which ends up being a lot of money). The talent in the minors is plentiful. Now just don't be slow to make some trades. Get your offers out there to the teams that have the players you covet. The Cubs are not the only team looking to upgrade. Even the teams on the bubble should be fielding phone calls from Jed. This is his moment. So I don't want to see him in the booth doing interviews with Boog and JD right now. I'd rather think he's working the phones with his own team of scouts and other team's GM's instead of wasting time telling us what he's up to. Plenty of time for that after August 1.
It will be very frustrating if some guys the Cubs could really want or need go somewhere else for less than what could have been offered by Jed because he was slow to the show or unwilling to close out what he started when he traded for Tucker.