I'll focus mainly on the last few years, but I think they've made a lot of moves "that could have helped the team when they had a chance to win."
Carlos Correa, Pablo Lopez, Tyler Mahle, Sam Dyson, Sergio Romo, Byron Buxton extension, Jake Odorizzi, Kenta Maeda, Kenta Maeda again, Nelson Cruz, Nelson Cruz again, Donovan Salano, Joey Gallo, Michael A. Taylor, significantly expanded payrolls for a couple years, Kyle Farmer, tendering Kyle Farmer, Anthony DeSclafina, Carlos Santana.
Not all have turned out well (see strikethrus) and some on TD have not liked their fairly deliberate approach that's led to a lot of transactions happening late in the offseason, but I generally haven't seen them staying put. They have the past two deadlines, but all in all, it seems like they are pretty active at making moves.