Which way will Rahm swing in upcoming election for aldermanic post?

I always thought one of the most humorous predicaments ever faced in electoral politics was that by Rahm Emanuel back during the 2008 election cycle.

EMANUEL: Political predicament reminiscent of '08

But watching the circumstances that are developing in advance of the 2019 elections for municipal office – including the seats on the Chicago City Council, make me wonder if Emanuel is going to face an equally-difficult predicament.

AT STAKE IS the 30^th Ward aldermanic post – one that represents a heavily-Latino ward Northwest, and one currently represented by Alderman Ariel Reboyras.

Reboyras, who chairs the council’s Public Safety committee, has developed a reputation as an alderman as a political supporter of the mayor. To the point where some people are inclined to think he’s “too close” to Emanuel, and that perhaps the ward and its residents would be better off with someone else.

That seems to be the line of logic that Jessica Washington Gutierrez plans to use in her efforts to challenge Reboyras in the Feb. 26 non-partisan elections.

So who will Emanuel side with when it comes to the election? Standard political logic says he backs the incumbent, particularly one who has been as loyal to Emanuel as Reboyras has been.

REBOYRAS: Thinks he's earned Rahm's backing

BUT THEN WE run into the complicating factor, Gutierrez is the daughter of soon-to-be retired Congressman Luis Gutierrez.

Luis would love it if his family were to become a part of that oldest of Chicago political traditions of multi-generations holding electoral office. Particularly since Luis himself was once an alderman back in the days of Harold Washington as mayor.

Luis also has become an Emanuel supporter in recent years – taking actions that helped bolster Rahm’s re-election chances the last election cycle in 2015. I don’t doubt he figures that the mayor owes him in the form of support of his daughter’s political aspirations.

So who does Rahm Emanuel wind up siding with? Or more important, who does he decide it will hurt him less to piss off?

Can Jessica's father gain her aldermanic seat?

REBOYRAS ON MONDAY said he thinks he has done enough to be entitled to the mayor’s support – and the financial support his campaign would receive from the mayor’s campaign coffers.

Which would mean squatting all over the aspirations of Jessica Gutierrez – who is engaging in her first political campaign and will try to feed off the votes of those people who liked Luis as their political representation and would like to see the name live on.

But does Emanuel really want to do that – particularly since it could result in having Gutierrez stir up resentment within the Latino segment of the electorate? Which could come back to bite him on the derriere.

Although several other Latino aldermen are saying they think the “right thing” for Rahm to do is stand by Reboyras. Either way, it’s going to be an Election Day headache as people will be parsing every word and action of Emanuel, even though my bet is that he’s going to go out of his way to say and do as little as possible.

JUST LIKE HE did back in the spring and summer of 2008. Remember that Hillary Clinton sought to be the Democratic nominee for president and figured she’d have the political establishment all locked up, thereby ensuring her an easy primary victory over all the other Dems who had the nerve to think they could run against her.

Would Hillary be president if Rahm backed her

Instead, we got the rise of Barack Obama, who took a few early primary victories and he wound up engaging Clinton in a brawl that dragged out all the way through the primary cycle. It wasn’t until the very end that Clinton conceded. Which put Emanuel, then a member of Congress from the Northwest Side and a former White House staffer during the Bill Clinton presidential administration in quite a political pickle.

His responses to “Obama vs. Clinton” questions were even more vague and nonsensical than the way Gov. Bruce Rauner now answers questions involving his "support" for President Donald J. Trump. Rahm didn’t come out and endorse Obama for president until the day after the final primary when Hillary herself conceded defeat.

Watching someone who, by nature, is outspoken and antagonistic as Rahm Emanuel having to keep his mouth shut was a sight to see. The idea we may get a repeat of it during coming months is something we’ll likely never forget.

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