Making history is never easy, which is something that David Ortiz is learning in his quest for 400 career home runs.

The Red Sox designated hitter enters Monday night just one dinger shy of the milestone, but the team’s recent road trip hasn’t been doing him any favors in terms of locales. Both Seattle and Oakland are notoriously pitcher-friendly ballparks, meaning that Big Papi will really need to crush one to make sure.

NESN Nation’s Dan Duquette breaks it down in the above video.

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