And, a chunk of that personal fortune - reports say almost half a million dollars - was plunked down on that by-election.
But, was it all a grave misjudgment? Dennis Williams, after all, is not a candidate of great political renown - in fact, he was not known as a politician even within Punta Gorda.
Barrow says it's a learning experience for him:
Shyne Barrow, Leader of the Opposition
"You know, brother Desho is a friend and a brother, and, you know, I. All he has to do is learn from this, pick himself up, look in the mirror and see everything that went wrong. And if he feels that he has an opportunity there, he'll keep working and keep going because the pendulum swings. And right now..."
Jules Vasquez
"Sir, he lost 3 to 1."
Shyne Barrow, Leader of the Opposition
"Yeah."
Jules Vasquez
"The pendulum noh swing that hard. He might need another 50 years."
Shyne Barrow, Leader of the Opposition
"Okay, well..."
Jules Vasquez
"Ok, sir, but but, you know, when we see certain things, it hints at a larger malaise when we see the UDP losing Monkey River, where famously one time the PUP only got two votes there, and you have, a candidate that should have."
Shyne Barrow, Leader of the Opposition
"His family is actually from there."
Jules Vasquez
"And the man lose Monkey River for the first time!"
Shyne Barrow, Leader of the Opposition
"But what I'm saying is….But how is that a larger, that is a micro."
Jules Vasquez
"Because what it says to me, and this is the same thing I saw in municipals: that people are not buying into the vision or the leadership of Shyne Barrow."
Shyne Barrow, Leader of the Opposition
"That is propaganda. I reject it."
Jules Vasquez
"Yes, but I continue to hear it, sir."
Shyne Barrow, Leader of the Opposition
"You hear that from people that want to be leader. You hear that from people in the United Democratic Party that want to..."
Jules Vasquez
"No sir, I hear that from regular people."
Shyne Barrow, Leader of the Opposition
"No you don't, you hear that from their supporters and them. There is a concerted…"
Jules Vasquez
"You don't want to hear it,but it..."
Shyne Barrow, Leader of the Opposition
"Sir, no, no, no it is I'm not disputing that. It's not being said, you know. Brother Vasquez, I have conceded that you receive those text messages. You receive those phone calls. I'm not saying that you are making this up, but this is all a part of a propaganda campaign."
Jules Vasquez
"Mike Espat get less than 50%."
Shyne Barrow, Leader of the Opposition
"Yes."
Jules Vasquez
"In two elections."
Shyne Barrow, Leader of the Opposition
"So, so, we are rebuilding."
Jules Vasquez
"So, it's historically close...but this time it went to 70%. So there is some, what we call, a vitiation of belief. The belief in the UDP has been voided. Nobody believes in your leadership."
Shyne Barrow, Leader of the Opposition
"No! The pendulum, the pendulum has swung. The pendulum has swung. Do not do that. That is propaganda, sir. That is a propaganda narrative. You hear this from people that have been ousted from the party."
Jules Vasquez
"Well, there are a lotta those."
Shyne Barrow, Leader of the Opposition
"And when we don't do it, you call them corpses and you say, how do you keep these people around? But then when I do it and it's reform, it's not reform. It's I di beef with everybody. There's some people that have to go. And when those people go, then they sit around and they pray for the downfall of the party and they bad mouth us, and they give you all of this misinformation. We are rebuilding, we are rebuilding."
"There is no one more suited to lead this party than me at this time."
Jules Vasquez
"Any defeat for a politician, it's painful and difficult. Did you consider or contemplate resignation?"
Shyne Barrow, Leader of the Opposition
"Absolutely not. That is absurd. That is ridiculous. I'm not John Briceno. I'm not going to quit on my party. I am a fighter. I'm going to keep fighting."