3. Game 5 of the 2019 NLDS
Dave Roberts has used Clayton Kershaw out of the bullpen multiple times despite his postseason struggles. And in the first few instances in which Roberts deployed this tactic, it worked. The first time Roberts brought Kershaw out of the bullpen was in the 2016 NLDS, where Kershaw was able to shut the door against the Washington Nationals.
Roberts would then bring in Kershaw out of the bullpen in Game 7 of the 2017 World Series. Kershaw dominated and the takeaway from that game was that he should have started (even though the entire reason the Dodgers traded for Yu Darvish was to start in that spot, but that is beside the point).
In 2018, Roberts brought Kershaw out of the bullpen to close out the NLCS against the Milwaukee Brewers. That series was an absolute slugfest and the Dodgers were depleted to their last resource, making Kershaw's save a welcome one.
It finally caught up to Roberts and the Dodgers in 2019. With a 3-1 against the Washington Nationals in the NLDS, Roberts called on Kershaw in a big spot out of the bullpen in the seventh inning. Kershaw ultimately got out of the jam against Adam Eaton and that should have been when his night was over.
But it wasn't.
Kershaw went back out there in the eighth and allowed back-to-back home runs to Anthony Rendon and Juan Soto to tie the game. Kenta Maeda, who should have been on the mound instead, took over and finished a clean eighth.
Roberts then one-upped himself and brought Joe Kelly into the game instead of Kenley Jansen in the ninth inning. Kelly allowed a grand slam without recording an out. Jansen came in anyway, but it was too little, too late.