This one will be tough to beat:
Hardball Dynasty – Fantasy Baseball Sim Games - Charleston 2-Bears Franchise Profile
This team has only been able to lose LESS than 90 games on threw occasions and the fewest losses ever was 85. They have finished last in the division 19 times and have a lifetime winning percentage of .353
The previous owner firechief did have cancer and was very sick. We have not heard from him since April so I fear the worst. I will say that my team has not been much better (I am in the same division) over the course of 26 seasons.