Yes, anything can happen, and our 4 rings in 10 playoff appearances , including 4 for 4 in the WS, makes it seem like the odds are actually better than they actually are.
People sometimes point to our 2004 championship as a wild card team, but that year, we had the 2nd best AL record and 3rd best in MLB. We were a top contender that year.
We had the best record in MLB in 2007. That was no crap shoot.
Many feel the 2013 season was a fluke, but we had the best record that year, too.
The 2018 season was far from a crap shoot.
We've had some really good teams that, to me, were a big step up from being called just a "playoff contender."
While I agree with you that DD went too far, and we may disagree on the degree of that, I can totally see why GMs go that extra mile to greatly improve their chances and hedge against injuries and/or too many down years from our players.
DD got us a ring. I can't really fault him too much for going the extra mile, and I was accepting of the projected consequences for the most part.