2. The Chicago Bears paid Montez Sweat the going rate
It is easy to say that the Bears overpaid Sweat when comparing him to Myles Garrett. Garrett signed his extension before the start of the 2020 season. That feels like an entire lifetime ago. The salary cap consistently goes up, and so do the salaries of the top-paid players. If and when Garrett is due for an extension, his deal will be up around $35M, which is more than Bosa's. The same can be said with Watt, or Micah Parsons and Maxx Crosby, who will get an extension soon enough.
The Sweat deal looks high because of the timing of it. When the rest of the new deals come in, Sweat will go from a top-five highest-paid edge rusher down into the 10-15 range, which is probably where most would rank him.
Sweat was getting the going rate, which is a slight tick-up from Rashan Gary. Gary is a bit younger and more productive on a per-snap basis, but Sweat is more reliable due to the lack of injuries in his past. If Sweat hit free agency, he would have signed for the same amount, if not more. The Chicago Bears could have tried to get into a bidding war and potentially lose, so they traded the pick to make it happen earlier.
The Sweat deals look high now, but lesser rushers will get similar deals in free agency, and the Chicago Bears can now focus on other positions with their high first-round picks. In the way that the perception of the Claypool trade changed over time, we can judge the trade now, but time will clarify whether it actually was an overpay or not.