On this Monday episode of Shoulda Bet More, we invite Dave Ross (@drosssports) of VSiN back to the pod! We go over everything we just saw this weekend in the NFL. Should the Lions be concerned with their poor defensive performances? What will the Chiefs do about Patrick Mahomes's potential injury? Could we see any surprise playoff teams at the end of the season? We look forward to tonight's Monday Night Football doubleheader and give you the bets that we are looking at. We also talk MLB free agency were Dave, a noted Mets fan, gives his reaction to the Juan Soto signing among the Mets' other moves. Finally, we also talk about what Bill Belichick and Mike Lombardi can do to transform UNC football into a playoff team.