He improved the pitching rotation superficially. But there was and still is nothing below the top 5 starters. While you can argue the injuries to Sale, Eovaldi and Price were unlucky, they were hardly surprising. Sale ended 2018 with some concerns. Price has had his issues since coming to Boston. And Eovaldi is a frequent visitor the the DL/IL.
The bullpen has actually been a pleasant surprise in some ways. I keep expecting Marcus Walden to fall apart, but the man is a Phoenix, repeatedly rising from the ashes of his own poor performances. Workman is having a career year. And Barnes, while up and down, was probably relied on too heavily by Cora early on. And now Josh Taylor looks like he might be carving out his own little niche for 2020. Still, the overall plan to grab a backup 1B in stead of another arm to give more depth in case anything went wrong strikes me as a very poor decision, especially since (unlike me) Dombrowski was aware of the Sox' financial situation.
But really the bottom line is this team has struggled since March, and while getting Cashner was a nice idea, we really have not seen anything else from Dombrowski. Rome was burning, and there was Dombrowski, fiddling away with Chris Owings and Joey Curletta. Meanwhile, the Yankees have the best record in the AL, and Cashman still isn't sitting still. Sure, it's extremely unlikely David Hernandez, Tyler Lyons and Trevor Rosenthal contribute in any meaningful way this year, but they are joining his ever-growing fleet of lifeboats. Meanwhile, the Sox have decided to sink or swim with whoever was on board in March and cling to the mantra "they need to play better." And that tactic is simply not working...