Not to throw shade on Tippett - we don't know how much he was being listened to - but it is amazing that the Red Sox have employed guys like him and Bill James (and Theo and his many disciples, for that matter) and have still made so many dumb and/or bad moves in the HWL era.
I am going to hazard some guesses as to the reasons behind some of these bad moves:
- Player projections still have very large error bars. And while it may be possible to project the probability of an injury for a player at a given age, there is a huge amount of randomness to injuries that no computer system will ever be able to resolve until Skynet is released.
- There is likely still a lot of room for analytics to improve in other areas. I'm thinking defensive statistics, catcher framing as just 2 examples.
- I've seen cases where very smart people look at the numbers and become enamored of their own theories to their detriment. Even theories backed by statistical analysis do not always work in the messy real world. I'm thinking "closer by committee", 4/70, etc.
- Sometimes people good with statistics are confused with being "smart". I recall one infamous poster discussing how great Kyle Weiland will be based on his best 3 innings out of 24 in 2011.
- Some "bad moves" are probably only bad in retrospect, but made perfect sense at the time. And some of the "bad moves" are not even "bad"; signing JD Drew, for example. Not even sure signing John Lackey can be called a bad move anymore. I'm quite sure you will get lots of disagreement on this forum if you called the trade-and-extend of Adrian Gonzalez a good or bad move.
- There are a limited number of talented players available for a team to acquire each season, and the market demand for those players can be quite high. And there are external pressures on a team like Boston to field at least a decent team each year. So even the "smartest" teams are forced to sometime step outside their comfort zone and roll the dice on acquiring a player for which there may be risks. And the Sox by definition are able to take more risks than say, the Pirates, so the likelihood increases of such a team making a bad move.
- And organizational behavior definitely came into play. We've had the Lucchino vs. Theo power struggle, the hiring of Bobby Valentine, and the pressure to win in more exciting ways. A person in Theo's position (or Dombrowski's now) has to answer to a number of stakeholders (Henry/Werner, the limited partners, etc). We just witnessed CEO Sam Kennedy somewhat walk back Dave Dombrowski's endorsement of Farrell ("ownership's decision"). Conflict is inevitable when you have a bunch of hypercompetitive type-A people each with different motivations, biases, etc. Managing that conflict into good strategic decisions is difficult, at least until Skynet is released.