My dad is out of town. What does that have to do with you? Well it means an extra pick for me to play with! Dad turned his pick over to me, so I get to try TWO strategies instead of one.
Week 5 of the NFL season gives us two interesting contrarian picks… Like Week 3, these picks feel REALLY wrong. However, in Week 3, it turned out the Vegas moneylines were right… The two wrong-feeling picks this week are Cincinnati (54% win probability, 25% picked) over New England (gasp! picking against Tom Brady?) and Chicago (50% win probability, 27% picked) over New Orleans (gasp! picking against the 4-0 Saints and Drew Brees after a huge Monday night win?). Two other ones are mild contrarian picks, NYG (57%, 49%) vs Phi and Car (57%, 52%) vs Ari.
For my own pick, I’m going to go all in on one of these picks. I don’t have any data to back this up, but I feel like New England tends to beat the Vegas line. Nevertheless, I’m trying to use a data based analysis instead of a gut feel, so I’ll go with the Bengals beating New England all-in for 14 points for two reasons: 1. They’re slightly higher in win probability, and 2. I live in Cincinnati (but die hard Packer and Cowboy fan!), and I know they’ll be on TV and it’ll be fun to cheer on my hometown team. I also “bucketed” the 57-60% probabilities and sorted by picked %.

For my dad, I’ll go Chicago all in vs. NO. No bucketing, just for the heck of it:

OK… let’s see if we can get a Cin or Chi “People’s upset” since they’re not Vegas upsets!
[UPDATE: New win probability data, new “all-in” pick for Dad!]