I don't know about that. To be sure, they haven't been good since the group that won the World Series broke up, but Moore has two pennants and a World Series ring which tops everyone currently working not named Friedman or Cashman, and Moore got his pennants and rings long after Cashman last got his.
As to the Brewers, it's fiction to believe they can trade All-Star pitching away without taking a step back. For example, without Hader, every pitcher takes one step forward and they're forced to rely on pitchers of the caliber of Gustave, Miguel Sanchez and Trevor Kelley to pitch in higher leverage situations. There is no way to trade Hader and not have the bullpen take a hit.
Moreover, the suggested return for any of the Brewers star players is all overblown. It's not the year 2000 any more, and teams don't trade elite minor league talent that is on the cusp of being major league ready. For example, when the Nationals traded both Max Scherzer and Trea Turner with team control remaining, they only brought back to Washington two players who are in AA, and two younger guys, Ruiz and Josiah Gray, who both have struggled significantly in their first tastes of the major leagues.
Trading Woodruff or anyone else, isn't going to bring back a hitter/s who immediately go into the middle of the order and put up an .850 OPS for years to come. It means the team will have less talent in the short run, which probably ends their competitive window regardless.