For 20 years Luis Gutierrez has billed himself as a backer of progressive Democratic politics in Chicago. But on March 17 he stunned even his core supporters by endorsing a Republican for town president of Cicero. And not just any old Republican. He backed Ramiro Gonzalez, the candidate handpicked by Ed Vrdolyak, the former Chicago alderman who’s had a big hand in running Cicero Republican politics.

“I think this is the biggest mistake of Luis’s political life,” says Joseph Mario Moreno, the Democratic candidate for town president. “I know Gutierrez has made a history of coming up with some strange endorsements–but joining with Vrdolyak? I don’t think anyone would have predicted that.”

The endorsement is even more surprising given that Gutierrez owes his political career to Mayor Harold Washington, whom Vrdolyak battled bitterly during the Council Wars of the 80s. In 1984 Washington plucked Gutierrez from anonymity–he was an out-of-work social worker driving a cab–gave him a white-collar job with the Department of Streets and Sanitation, then slated him to run for alderman of the 26th Ward. Vrdolyak supported Gutierrez’s opponent in that race, Manny Torres–and Torres probably would have won if Washington’s blessing hadn’t brought out black voters, virtually all of whom went for Gutierrez.

After Washington died in 1987, Gutierrez spurned his former allies and endorsed Richard Daley for mayor. In return, Daley created a new Fourth Congres-sional District, whose bizarre boundaries guaranteed the election of a Hispanic, and in 1992 endorsed Gutierrez for Congress. Ever since, Gutierrez has always been backed by Daley–and has always been unbeatable, usually winning over 75 percent of the vote.

Of course Gutierrez isn’t the first independent politician who got to Congress by joining the machine. Former north-side congressman Sidney Yates did the same thing back in the 1940s. As Yates once explained it, peace with the machine was the price he was willing to pay to pursue a progressive agenda in Congress. Gutierrez offers a similar explanation–and has an equally liberal voting record. The difference is that once Yates got to Congress, he pretty much stayed out of local politics, even during the heated north-side campaigns of the 60s and 70s.

In contrast, Gutierrez can’t seem to stay out of a local fight. Sometimes he endorses independent-minded politicians, such as 22nd Ward alderman Ricardo Munoz and state senator Miguel del Valle. And sometimes he endorses machine stalwarts, such as former 35th Ward alderman Vilma Colom and First Ward alderman Jesse Granato (now in a close runoff race with Manny Flores, who used to work for Gutierrez).

Gutierrez says he tends to support independent progressives–Democrats who, like him, got their start in Washington’s movement. If he deviates, as he did by endorsing Granato, it’s as a favor to Daley. According to Gutierrez, his ties to Daley are so strong he’d support almost any local politician Daley was willing to put his weight behind.

“I have endorsed Jesse Granato for reelection–I supported him because Mayor Daley indicated he wishes Jesse Granato to have another term in the City Council,” says Gutierrez. “The mayor asked me to support him, and the mayor has been very supportive of me and my initiatives. Put it this way, I think Manny Flores is a wonderful young man. But if I have to decide between Manny Flores and Mayor Daley, I’ll choose Mayor Daley.”

Does that mean Mayor Daley asked Gutierrez to support Gonzalez? Gutierrez says no. And he says Vrdolyak didn’t have anything to do with his endorsement either. It was a strictly personal decision. “Cicero is a huge part of my congressional district, so it’s natural that I would make an endorsement there,” he says. “I sat down with Mario Moreno–I didn’t just rule him out.”

The problem with Moreno, Gutierrez says, is that he has too many commitments–he’s a lawyer with a Loop-based practice, and he’s a member of the Cook County Board of Commissioners. “I asked Mario, ‘Are you going to close your law practice and are you going to resign from the county board?'” he says. “I feel it’s very important that we have a full-time representative in Cicero. He said he has to keep the law practice open. He said he wants to keep three jobs because he needs to send his kids to college. The motivation of sending your kids to college is an excellent motivation for working. But the motivation for public service is to help other children go to college–to help other children achieve. We have an unfortunate situation where the Democratic nominee is not only double-dipping but triple-dipping. I can’t support that.”

In contrast, Gutierrez says, Ramiro Gonzalez is “a wonderful young man–one of ten children when he was growing up–who has cleaned up Cicero.”

Gonzalez became town president last year when his political mentor and predecessor, Betty Loren-Maltese, was forced to resign following her conviction on federal racketeering and corruption charges. Loren-Maltese, like Gonzalez, is aligned with Vrdolyak, who built a political base in Cicero after giving up his long-standing ambition to become mayor of Chicago.

News of Gutierrez’s Gonzalez endorsement broke on March 17. “I am convinced that there is no corruption left in Cicero,” Gutierrez told Tribune reporters Liam Ford and Sabrina Miller. “Ramiro is a wave of fresh air in this town.”

Few, if any, longtime Gutierrez watchers believe the congressman was telling the full story about why he backed Gonzalez. And in the days following the endorsement they came up with all sorts of convoluted theories as to why he’d apparently joined forces with Vrdolyak.

One theory is that Gutierrez is looking for backers so that he can run against Daley for mayor in 2007. “Luis wants to be mayor,” speculates one northwest-side politico who didn’t want to be named. “He’s tired of having to kiss Daley’s ass all the time.”

Another theory is that Gutierrez made his endorsement to undercut Moreno. “You know Louie–he’s a sneaky one,” says another northwest-side observer who wanted to remain anonymous. “He’s worried that Moreno might get too powerful if he gets elected town president.”

Moreno and his backers have another theory, which involves some complicated behind-the-scenes maneuvering by Daley, Vrdolyak, and leaders of the Hispanic Democratic Organization (HDO), the mayor’s chief political operation in Hispanic wards.

According to Moreno, he and Gutierrez did indeed talk about an endorsement in the Cicero race, but the conversation went nothing like the congressman’s account. “We never talked about college tuition,” Moreno says. “He did ask me about my law practice, and I told him that the law office ran itself. I have lawyers who work for me–the firm has never kept me from doing my duties as a member of the Cook County Board.”

Moreno also says he told Gutierrez he would resign from the county board should he be elected town president. “This whole thing about Gutierrez opposing me because of my outside jobs is made up,” he says. “Did the congressman tell you that his candidate, Gonzalez, also has more than one job? He’s the town president and he’s on the school board. Why doesn’t Louie object to that?” Moreno adds, “Luis told me he had a meeting with the mayor in the afternoon. He said he would follow the mayor’s lead on who he endorses.”

Why would Daley tell Gutierrez to back Gonzalez–given that Vrdolyak and Daley remain bitter rivals?

Moreno won’t speculate, for fear of getting involved in a public fight with Daley. He does point out that this is his second run for president of Cicero. Back in 2002 Loren-Maltese soundly defeated him. “I ran alone in that election,” he says. “No one supported me because no one thought I could win.”

This time around he’s received endorsements from many Democratic politicians including, surprisingly, Cook County commissioner Roberto Maldonado, state representative Willie Delgado, and other members of Gutierrez’s political organization.

So why would Gutierrez back Gonzalez if his allies are backing Moreno?

“I’ll tell you what happened if you don’t use my name,” says someone in the Moreno campaign. “Gutierrez agreed to support Gonzalez as part of a deal having to do with the 12th Ward aldermanic election.”

According to this theory, Vrdolyak persuaded former 12th Ward alderman Ray Frias to drop out of the runoff and concede the race to George Cardenas, HDO’s candidate. “Vrdolyak and HDO cut a deal, and the net effect is that we got fucked,” says the Moreno camp source. “We were counting on HDO support. But Vrdolyak got Frias to drop out, and in return HDO agreed not to come into Cicero. The idea is that HDO will let Eddie [Vrdolyak] run Cicero for the moment. It’s only a temporary truce. HDO still has its sights on Cicero. They’ll come back in 2005 and run Marty Sandoval [another HDO-aligned politician] against Gonzalez. Luis doesn’t care. He’s such a puppet he’ll do anything for Daley–even if it means getting into bed with Vrdolyak.”

But there might be a hitch: “I think I will win–with or without HDO,” predicts Moreno. “I think I’ll surprise them all. That’s why I say Gutierrez is making a big mistake. It’s just like in the 35th Ward, where Gutierrez supported Colom and Rey Colon won. These guys think all that matters is the deals they cut. They forget about the voters.”