Joe Trippi, best known for being Howard Dean’s campaign manager in the 2004 presidential primary season, spent days in Chicago in September and October advising Cook County Sheriff Tom Dart on his possible run for mayor. But two weeks ago, the sheriff announced that he won’t run after all, due to family obligations.

Trippi—who had just returned from Mexico, where he rested after helping to run Jerry Brown’s victorious race for California governor—called me this morning to discuss Dart’s decision. Here, highlights from our conversation:

CF: You were in the midst of the Jerry Brown campaign when you were advising Tom Dart?
JT: Yes. I would hop on a United flight on my way out to California [from his home in Maryland] and stop in Chicago, spend two or three or four days in Chicago, and then go out to California for two or three days.

CF: Why did Dart drop out of the race?
JT: Two things. He told me he had to get comfortable with leaving a large part of his job as sheriff on autopilot during the campaign. Also, he was a father who had always gone to every one of his kids’ games. The month I was involved with him, he wanted me to help him get comfortable with [the question], How much time am I going to have to spend to [run for mayor]? No matter how good the fundraising was going, he would spend hours and hours on fundraising calls or going to lunches and dinners to raise the money, and he would come home late and miss a family dinner. Or something big or important was happening at the sheriff’s office, and he would leave the [fundraising] and go do his job as sheriff. He just never got comfortable with how he was going to pull off a run for mayor, do his job as sheriff, and be there for his children. In the end, the biggest factor was the kids—breaking the cycle of them being used to him being home for dinner, being there in the morning for breakfast, being at their games.

CF: Many people in Chicago thought he was hiding behind the excuse of  wanting to spend more time with his family. Did you ever meet at his home and get a sense of his family?
JT:  One day in particular, I spent the entire day at his house. You could just see his interaction with his children. He didn’t run [for mayor] for all the right reasons. In my experience, the guys who actually think hard about what it means to abandon your job or your family, even for five months, these guys tend not to make the race. And we’re getting more of the guys who would run over their best friends—those are the guys who run for office.

CF: “Run over their best friends?” Is that a dig at Rahm?
JT:  I think it describes a lot of people who run for office these days. I think Rahm left the chief of staff job at the White House right before the biggest electoral disaster that the Democrats have seen for 50 years. He was going to do it because it was right for Rahm. That’s politics. 

CF: Was Dart’s wife opposed to his running?
No, not at all. Patricia said, “You go, I’ll deal with this.” But kids aren’t like that. Kids don’t know that they’re not supposed to [ask], “Why weren’t you here when we were having breakfast?”

CF: Some people said that with Rahm in the race, Dart was having trouble raising money.
JT: That’s all garbage. I was there. He was having very good conversations with labor leaders, money was coming in, and he had plenty of money in the account. He was not having a hard time at all raising money.

CF: Could Dart have gotten the endorsement of Mayor Daley and his brother, Bill?
JT: We weren’t counting on that, and we believed they would be neutral—or support Rahm behind the scenes or outright. Tom wasn’t running to be dependent on any of those kinds of endorsements. Under normal circumstances, he would have expected [their endorsement] but not with Rahm involved.

CF: Have any of the other candidates for mayor here asked you for help?
JT: I haven’t talked to anybody. But I’m not going to tell you, “No, I won’t do it.”

CF: What if Rahm calls?
JT: I don’t think that’s going to happen. He’s not the kind of person who would look with appreciativeness on me even entertaining the idea of working for Tom Dart. So I think having crossed that line, I doubt I’ll get a call from him.

CF: Rahm is gathering support from all kinds of CEOs of major corporations. Will his success at fundraising make it impossible for anyone else to beat him?
  He’s a formidable frontrunner. I don’t think anyone can question that, and he’ll have more money than he needs to have. Cautionary note: That can often start to work against you. Somebody will emerge as the challenger to the 800-pound gorilla. My guess is there will be a runoff [the nonpartisan primary is on February 22nd; if no one wins a majority of votes, the runoff for the top two vote-getters is April 5th]. If Rahm gets in that situation then anything can happen. People start looking around and start to look at the alternatives to the formidable frontrunner and, if there’s a viable alternative, it can give Rahm trouble.

CF: While I have you here, will Howard Dean or [just defeated Wisconsin Sen.] Russ Feingold challenge Obama in 2012 for the nomination?  
JT: I don’t believe Howard will do that—it’s not really who he is. I think it’s much more likely it will be an independent like a [New York Mayor] Michael Bloomberg. And no, I don’t think Hillary will challenge Obama.