of course, it's quite a personal choice, depending on how much you need to be at that game, and what happens if you don't get there on time -- balanced against your desire to try p.s.

You would be inserting 2 more stops in your itinerary, in the late evening through JFK and IAD. It might go badly if there were weather problems.

here are some steps you can do to assess the risk, maybe, and make it a bit more concrete:

Perhaps you might want to make up a table of contingencies based on UA's schedule, and see how many "outs" that leaves you if something goes delayed at any point. For example, point by point, at the times in your itinerary -- "what if there's a delay at SFO, what flights can still get me there?", "what if there's a delay at JFK, what flights can still get me there?", "what if there's a delay at IAD, what flights can still get me there?"

From that perspective, being in SFO early in the day, for example, is a lot better than being in JFK late in the evening...

-- one better idea -- how about doing the complex routing just on the return, and keeping the outbound simple, to protect against delays?