A little over 2 years ago, Neil Huntington was fired and Ben Cherington was hired as GM. We are into our 3rd off season with BC. I think we can make some observations about BC.
First let's understand we have only seen him during "build" mode. He inherited a poor team and a weak farm system with few top prospects.
His approach during build mode has been to trade established players (Marte, Bell, Frazier, Musgrove, Stallings, etc.) for primarily prospects with high ceilings. He has gotten very few MLB ready players in his trades except for a few pitchers. Instead he has filled the farm system with Low A to AA players who have some outstanding skills but also have the risk of flopping. Only Bednar has had any impact at the ML level to date. The others either have not made it to the bigs or have been average at best (Crowe, Wilson). There are some who look very promising (Contreras, Yajure, etc.) but we won't know until the 2022 season is over about them.
He has picked up a number of players from the scrap heap. Tyler Anderson, Yoshi Tsutsugo, and Ben Gamel being the ones who have contributed to the team. Anderson was traded off for prospects at the deadline. Most of the others either flopped (Tom, Fowler, Cahill, etc.) or are being given a little more time (Alford, Park).
As for the Polanco handling, he was under contract and they were going to pay him no matter what. So they gave him a chance to make himself tradeable...he didn't.
The choosing of Shelton as manager was OK but not great. Shelton has done a really good job of motivating the team to play hard all season. He is learning on the job quite a bit. Unsure if he will be the guy once the team gets better, we shall see. I think the jury is still out on the other coaches at the major league and minor league levels. Again, we shall see.
He has given players a chance to prove themselves, though Will Craig, Jared Oliva, and now Mason Martin might disagree. Tom, Kuhl, Brault, Ponce, Moran, Evans, EGon and others had opportunities but they didn't show they were better than other options. When he has seen enough and they are not producing, he will move on. Maybe he hasn't given young guys he inherited that same leeway he has given guy he has chosen, but to me the jury is still out on this. He is certainly giving Keller, Newman, and Tucker chances.
He has not been afraid to rock the boat. He is willing to trade established players if he can get the return he wants. The Marte trade looks great for us. The other trades (Bell, Musgrove, Frazier, and now Stallings) are still are to be evaluated.
BC is willing to have the fans endure terrible seasons while he is building the team. I see 2022 as another bad year with the only bright spot is prospects showing up thru out the year. Really 2023 is the year BC needs to start showing that the organization is improving. If they are still awful in 2023, BC might be on a short leash.