I see the Freeman and Swanson situations as very different. Freeman already played out his first big contract. He was faced with the choice of being a Brave for life or making maximum dollars during his career. His agent completely lost the trail and he ended up not being a Brave for life and not maximizing dollars. Swanson played out team control. That tells me he turned down the first big contract choosing to maximize the dollars he'd get as quickly as possible. Those are two different paths. I suspect those that are currently on contracts buying out arbitration will be talked to about extensions at appropriate times. Those like Fried that choose to play out team control are likely choosing the fastest way out of town and won't be resigned once they hit FA.
The best on paper roster in MLB isn't guaranteed a world series win. That is why they play the games. Continuing to permit talent like Freeman, Swanson and (potentially) Fried to leave the organization without any return is a tough strategy to understand. That's why I'd be in favor of dealing Fried for the right return. It might not maximize the Braves chances of winning a title this year or next, but with the team's current window, the right deal for Fried could set up the rotation for years to come.
A holistic view should be applied to a franchise each year. This should include where a team is on talent at both the ML and miL, where the team is in regards to contention, how committed you are to capturing a trophy, how committed you are to maintaining a competitive window, etc.
I personally feel differently depending on the situation. I (famously or infamously depending on your viewpoint) called for Freeman to be traded during the middle of the rebuild, theorizing that he was more valuable as a trade piece in building a competitor than as a long term piece as a competitive team. That was both right and wrong - wrong because the Braves became competitive faster than I expected and won a WS; right in that the Braves ultimately lost Freeman in FA for nothing more than a watered down pick.
I also felt that without a Freeman trade, the farm would be dry by the time the team needed another influx of key contributors in order to remain competitive. Again, both right and wrong but mostly wrong to this point since the Braves payroll pushed into dollars that no one expected to see (at least not me) and found some gems that were statistically unlikely (Strider, Harris, Contreras, Grissom). But we've finally gotten there in all likelihood with the farm where all the talent looks to be at least 4-5 years away AND the payroll appears to be close to being maxed out.
Swanson was different in that the Braves were clearly contending, he played a position of need with no real alternative around, and really didn't blossom in value until his FA year. Trading him would have been pretty pointless given the circumstances.
Which brings me to now. The Braves
appear to be tapped out on payroll and are facing big gambles at a number of positions (LF & SS being the main ones), have few internal options - yes, Grissom get's a shot and Wash
likes him, but what would you expect him to say -, and have no money to buy fixes. They are gambling that things go just right and they have great injury health, which is what most teams have to do each and every year.
I think rolling with what you have is certainly a viable alternative. But I also see the merit in a Dodgers/Rays type blend of approaches - spend money like a large market team but stay under the tax, extend the players you want to keep if they'll sign, trade those that won't extend at best value with as little disruption to the ML team as possible. That's why, while not advocating for a Fried trade, I certainly would be open to exploring what a return would look like from potential suitors and be willing to pull the trigger if I got what I wanted - even in the face of what appears to be a reasonably good contending opportunity for 2023. Your 2023 gamble goes up (already a year of gambles) but, if the return is right and pays off, your 2024 and beyond becomes much brighter and allows you to bridge to the new wave of talent starting up through the low minors.