2) The Red Sox chose to stand pat at this year's trade deadline and that left them directionless
The Red Sox were one of the surprise teams of the American League this season. They were 56-50 at the deadline, and just 2.5 games out of a playoff spot. With that in mind, the Red Sox had a chance to either go all in for their unlikely playoff berth, or assume the odds were stacked against them like Bloom said they were and trade some of their assets for pieces to help them win in the future.
Instead of picking one or the other, Bloom decided to stand pat. Bloom himself gave Boston the label of "underdogs" which alienated one of the most passionate fan bases in all of baseball, and that in itself told the team that he thought they weren't good enough and weren't worth trading prospects to improve.
The Red Sox were coming off a really strong month of July which saw them win 15 of their 23 games, and propel themselves right into the thick of the playoff picture. The Red Sox, a team with seemingly unlimited resources, had a chance to make a big move, acquire the ace this team had been missing, and make a push for the playoffs. They failed to do so. And guess what, if Bloom thought they weren't good enough, he could've traded away players on expiring deals to continue improving what's become a really good farm system. That didn't happen either.
Bloom did nothing other than acquire Luis Urias and the team has gone under .500 since the deadline. Boston had a 24.6% chance to make the playoffs per FanGraphs on July 31 and that's down to 0.3% on September 14. They're still well-equipped to potentially win in the future with a great farm, but Bloom could've either improved the farm even more to help them win sooner, or trade away a prospect or two to help them win right now. Doing nothing was never an option, and that's what he went with.