To your post, yes the best player available is the best option.
But people who suggest Jed will never get the superstar and will always only settle for good players are right. But is it Jed who is risk adverse or Tom? Will Tim just not do it because he knows on the back end the deal suck? We don’t know. But let’s say it is Jed. So he doesn’t want to giving a 10 year deal to a superstar. For this season, let’s use Tucker. Let’s make it simple, 10/$370. Assuming Tom is not ever going to play over the LT on a regular basis, what happens if Tucker ends up with injuries most years that makes his contract an albatross. Not even Kris Bryant bad, but bad. The Cubs ownership won’t go over the LT to bring in other good players, they will just allow the team to try being competing with a waste of $37M a year on the roster. At least with good players and less years they aren’t wasting as many years or money if that player end up with problems staying healthy or maybe just not being very good. Look at the Phillies. They carried Castellanos and still added. They had Realmuto for a high salary, Nola too. But they signed Schwarber again. Hell, the Dodgers were paying guys not in the playoff roster more than some teams payroll. They have carried bad contracts for years. Even before this unprecedented spending of money. Padres, who are said to be broke. Spent money even with a bad Bogaerts contract. There are more. But the point is, I don’t see Tim allowing that. Cubs would just have to ride it out and suck. A major market team should be able to compete, even with a bad contract or two. And until Rom gives the green light that he will go over the LT on a semi regular basis, I don’t really blame Jed for being risk adverse. One wrong mega contract could set the team into sucking for a decade.