Phil v. Red: unanswerable, but let's at least consider the context
(This entry prompted by Red Auerbach's son's comments about his dad winning eight championships in a row, as quoted at the Deadspin post here.)
I don't get why no one talks about one of the most relevant facts: Red Auerbach only had eight or nine teams in the league when he was winning. Phil has had between twenty-seven and thirty. (Bill Simmons would argue at this point that the league is diluted, but the pool of available players has grown by at least three to four times in that time, hasn't it?) Simply as a matter of probability, it's a lot harder to win a championship today.
Let's also note that Phil won six championships in a row himself. From 1996 to 2002, the only non-Phil championship happened while he was out of the league.
I don't know if he's the greatest coach ever, because there are just too many intangible variables to consider in answering that question, but I think his coaching record is the best ever by a wide margin.
Beaneball by Jason Wojciechowski is licensed under a Creative Commons Attribution-ShareAlike 3.0 Unported License.