I did a little quick research on past storms that have had a similar path over Cuba/Southwestern Haiti as projected by the NHC and below are those storms and how strong they were post-Cuba making landfall in the Gulf. All of these storms went across some high elevations of Cuba or in fact tracked across a large portion of Cuba and were able to steadily or quickly recover in the Gulf. In addition, most of these storms occurred around the same time as Isaac and into the peak of Hurricane Season. Keep in mind, I'm not trying to suggest or predict Isaac will have the same fate as the ones listed below, I just felt it was an interesting food for thought. My overall point here is that even though Isaac could go over Cuba and scrape the Southern part of Haiti it doesn't necessarily mean it's out when it's down. It has a decent potential to recover quickly as long as it doesn't do anything wacky like sit and stall destroying what circulation is left once it's in the Gulf.
I was gonna post some honorable mentions, but my list would have been a lot longer.
Great Middle Florida Hurricane (August 16-27, 1851)
Category Three (US Landfall)
Major Hurricane 3 (September 8-18, 1875)
Category Three (US Landfall)
Hurricane 5 (September 1-13, 1878)
Category Two (US Landfall)
Indianola Hurricane (August 12-21, 1886)
Category Four (US Landfall)
Major Hurricane 4 (September 18-October 1, 1894)
Category One (US Landfall)
Great Galveston Hurricane (August 27-September 15, 1900)
Category Four (US Landfall)
Hurricane 2 (August 8-17, 1928)
Tropical Storm (US Landfall)
Major Hurricane Cleo (August 20 - September 5, 1964)
Category Two (US Landfall)
Major Hurricane Georges (September 15-October 1, 1998)
Category Two (US Landfall)
EDIT: In other news, Isaac may be finally starting to develop a vertically stacked circulation, RECON is finding peak flight level winds as strong as 62kts. or 71mph. Surface winds are coming in at 56 kts. We might see winds bumped up into the 55-65mph range come the 11am advisory.
Peak (10s) Flt. Lvl. Wind: 62 knots (~ 71.3 mph)
SFMR Peak (10s) Sfc. Wind: 56 knots (~ 64.4 mph)