I think he could have, but maybe not, we will never know. A lot of times a GM is working under a mandate, DD was a perfect example of this. Despite his reputation, if you go back far enough he was the guy who hoarded prospects, filled up a farm, and didn't make the big blockbuster.
Under Henry's direction, or perhaps on his own Ben may have come to the conclusion that it was time to switch direction and add to the MLB team with a big piece. I don't believe in this, but wouldn't be surprised if that's how things went if he had stayed here too. Maybe we never win in 2018, maybe Ben trades for someone else who stays healthy over Sale and the team doesn't get broken up in 2020....who knows.