4 front office mistakes that have crushed Dodgers playoff hopes last two seasons

Awful 2023 trade deadline (in retrospect)

Either Friedman tried to get too fancy or he didn't really believe in the 2023 roster's World Series chances. That's all we can deduce from the Lance Lynn, Joe Kelly, Amed Rosario and Kiké Hernández acquisitions before this year's deadline, especially when guys like Justin Verlander, Max Scherzer, Jordan Montgomery, Michael Lorenzen, Tommy Pham, Jake Burger, Mark Canha, Paul Sewald, Jordan Hicks and others were available.

There's just no possible way you can convince us the Dodgers were either out-bid on every better player or refused to meet the asking price on everybody. Friedman's deadline deals have historically been calculated, especially to minimize risk, but the 2023 roster was overachieving and proved it deserved proper supplementation. His moves were the equivalent of using scotch tape to support a wobbly shelf.

How did this work out for them? Lance Lynn ended their postseason by surrendering an MLB-record four home runs in a single inning against the Diamondbacks. Rosario was left off the NLDS roster. Hernandez went 3-for-8 and shouldn't have been a featured source of offense. Kelly logged 1.2 scoreless innings in losing efforts.

Whoops! We forgot about Ryan Yarbrough, too, who stumbled a bit in the second half and then was left off the NLDS roster.

Swap out two of these guys for real, impact deadline moves and we're probably looking at a different October result.