He never made a cent in his life that he didn't waste.

[sitifan]

He was brave . He never made a cent in his life that he didn't waste.

What does the above passage mean?

[Gillnetter]

He was brave . He never made a cent in his life that he didn't waste.

What does the above passage mean?

He was brave = He had no fear.
He never made a cent in his life that he didn't waste = He spent all of the money he made and he spent it on worthless items.

I don't really understand how these two sentences work together.

[Raymott]

"What was he like?" quavered the old man.
"Well, he was foolhardy, which led to his death," said Bill with a wry smile. "He was brave. He never made a cent in his life that he didn't waste."
"How did he die? Were you there?"

Even seeing the sentences literally together, it's hard to know how they fit thematically together. It's not traditionally held that being a wastrel means that one is brave.
Perhaps he was brave in having no fear of poverty or of debt collectors, etc.

[sitifan]

Chapter 9: Breathe In Breathe Out « Sarifina85
Every part of me screamed to not answer this human’s question. My instincts demanded to keep this part of my past to myself. I looked at Tolliver’s descendant again. Tolliver had been a good man, too good for his fate. He had made a noble sacrifice, and that sacrifice deserved to be told.
“Yes,” I finally answered, struggling to keep my voice even and emotionless. I tried to steady myself by focusing on my breathing. Breathe in—breathe out. “Tolliver was my friend.” I knew I had not completely succeeded, and could hear my voice close to breaking. I had never spoken of Tolliver’s death. Not even to my wife after I had returned home, but Tolliver’s descendent deserved to know the kind of man his ancestor had been.
“What was he like?” the human prompted, his voice breaking as well.
“Well, he was foolhardy, which led to his death,” I explained ruefully. “He was brave. He never made a cent in his life that he didn’t waste,” I continued, actually remembering fondly all of the times Tolliver lost money to me as we passed time between moving to various battle encampments with various games of chance.
“How did he die? Were you there?” the human asked.
I struggled not to sigh and answered, “Yes, I was there. I saw him get shot by a Northern sniper in the woods about twenty miles from here. He was slow because he was starved. We all were. About the middle of the morning, a cold morning, Tolliver saw a boy in our troop get shot as he lay in poor cover in the middle of a field. The boy was not dead, but painfully wounded. But he could call to us, and he did, all morning. He called to us to help him. He knew he would die if someone didn’t.” I looked out at the crowd; they were reverent in their silence, showing the proper respect for poor Tolliver.