Depending on how much less money, I'd say the second option. If we're talking in the 9-12 million dollar range as opposed to the 15-19 mil a year deals, I'd trade that in for rings for sure.
Would you rather own a small market team with a below average roster, no draft picks and 20 million dollars in cap space or a big market team with a slighty above average roster, all your picks and in the luxury tax?