I was looking at it.

I've had the best record 3 out of 12 seasons. Ern has the same, Theo had the best record 4 times out of 12 seasons, Frank once, Boogs once.

Boogs has been to the finals 4 times (never won though)
Theo with all that reg season success only has 1 title
I was the first to win multiple titles. Won 2 out of the 3 times I had the best record. Got to the conference finals from the 6th seed once.
Ern did everything I've done (though he did it after me) but in his low seed run, he won a ring.

Last season was the tie breaker. He got #3.

Looking at it:
Ernie -
Career record = 294-308 (10 seasons)
Career win % = 48.8 (14th all time)
Titles = 3
Best rec = 3
Best avg = 1
Winning seasons = 5 (of 10)

Theo -
Career record = 451-275 (12 seasons)
Career win % = 62.1 (1st)
Titles = 1
Best rec = 4
Best avg = 3
Winning seasons = 10 (of 12) and the two losing seasons were 30-32 and 28-30

Boogs -
Career record = 430-296 (12 seasons)
Career win % = 59.2 (3rd)
Titles = 0 (4 finals appearances)
Best rec = 1
Best avg = 1
Winning seasons = 10 (of 12) And he's the highest earner in the league

Commish -
Career record = 376-350 (12 seasons)
Career win % = 51.8 (10th)
Titles = 2
Best rec = 3
Best avg = 3
Winning seasons = 5 (of 12) First to win multiple titles

Shawn -
Career record = 386-340 (12 seasons)
Career win % = 53.2 (8th)
Titles = 1
Best rec = 0
Best avg = 0
Winning seasons = 8 (of 12)

Ern has a case, mostly built off playoff success since he's won 3. But overall, if Theo got another ring or two...

Hell, I was 1 game away from 3 titles myself and all my stats are better than Erns for the most part. I get one more and I got a good case.