Axworthy, who has mused publicly for months about a leadership bid, sent an email to family and friends last week. The email alludes to past financial troubles, including bankruptcy, and asks for help.
"It is true I've had some hard lessons in my life, but I've gotten back up every time I've been knocked down," the email, obtained by The Canadian Press, states.
"Those lessons ... have helped me become the person I am today and has led me to the place I feel I should be. I would like to continue to advance my efforts by running for leadership of the Liberal party.
"To support me in the fight for new direction in Manitoba, I am asking for a small donation of $5 to help fund my campaign."
So far, there are two candidates to replace outgoing leader Jon Gerrard, who announced his plan to quit following a disastrous 2011 provincial election campaign that saw the Liberals reduced to one legislature seat and 7.5 per cent of the popular vote.
Rana Bokhari, a Winnipeg lawyer, and Dougald Lamont, the owner of a marketing company, entered the race earlier in the summer and have picked up endorsements from some high-profile party members.
Axworthy said he is taking his time before making the decision on whether to officially enter the race.
"That letter is another kind of final step in saying 'is this worth doing?'" Axworthy said in an interview.
The Axworthy name runs deep in the Liberal party. His eldest brother, Lloyd, was a longtime federal cabinet minister. Another brother, Tom, was a principle secretary and speech writer to former prime minister Pierre Trudeau.
But Bob Axworthy has not to date had the same kind of success. He has at times struggled financially and owned a Winnipeg hotel in the 1970's when it went under.
"I believe that if we never fail at anything, it means we haven't tried much either. I acknowledge those past mistakes," his email to friends and family states.
Axworthy surprised many when he finished a strong second in a 2012 byelection in Fort Whyte, a Progressive Conservative stronghold. More recently, Axworthy has been doing non-profit work in Winnipeg's core area.
The first Liberal leadership debate is set for Saturday, September 21. The deadline for candidates to enter the race is Sept. 25. The party will choose its new leader Oct. 26 via a one-member-one-vote system.