Auerbach built the Celtics from the ground up. Jackson, with Chicago and L.A., inherited massive talent. While he's been in a position to succeed, it's also true that no one else in today's game could have done as well. But he still can't touch Auerbach's accomplishments.
Auerbach not only didn't have significant talent at Boston, when he got there, the team itself was on shaky ground. He drafted Bob Cousy, with reservations, Bill Sharman, K.C. Jones, Satch Sanders, Tom Heinson, Sam Jones, Frank Ramsey, John Havlicek, and traded for Bill Russell, who was the culmination of Auerbach's vision. But he didn't just show up. Auerbach had to pull off a significant trade to get him.
Keep in mind that there was no free agency at the time, so a Shaq couldn't just decide he'd like to play in L.A.
When this group began to age, Auerbach brought in various reinforcements - Don Nelson, Mel Counts, and other guys who were either underrated or else considered over the hill. By this time he had quit coaching and was managing things instead.
After the Russell era ended, Auerbach had the Celtics back in no time, building around Havlicek, JoJo White, and Dave Cowens.
After that group fell apart, Auerbach audaciously drafted Larry Bird as a draft-eligible fourth-year junior (the rule was soon changed) and signed him after his senior year. Then he swung a deal which got Robert Parish and Kevin McHale, thus giving the Celtics one of the all-time great frontlines.
He almost did it again when Len Bias, tragically, died.
He also did much of his great early work with the background of segregation and a virulent racism aimed at his African-American players.
Is Jackson a great coach? Hell, yes he is. Is he better than Red Auerbach?
While he's as close as anyone will get, and should win more titles than Auerbach retired with, Auerbach was a better psychologist and great on game management as well. It's going to be hard to top his accomplishments, and since Jackson is clearly still bugged by Auerbach's psychological antics, it's clear that he's not convinced himself that he's ready to snatch the pebble from Red's hand. He should end with more titles, but it's worth remembering that Auerbach wasn't much older than Jackson when he retired. Had he coached a few more years, he would have gotten four or five more.