For those familiar with sheriff’s many scandals, trial feels like ‘Groundhog Day’

The trial to remove St. Louis Sheriff Alfred Montgomery got off to an exciting enough start. The sheriff entered the courtroom handcuffed and looking haggard, wearing a charcoal suit less flashy than what had once been his standard fare. Assistant Attorney General Greg Goodwin, whose job this week (and possibly next) is to prove Montgomery is unfit for office, argued that Montgomery had betrayed city residents’ expectations “not to act like a king.” Montgomery’s attorney, retired judge David Mason, basically called the Attorney General a liar in his openings. Journalists packing the jury box typed as feverishly as the court reporter. 

Flash forward 90 minutes, and during the trial’s first break, reporters were outside the courtroom describing the proceedings, which had flagged considerably in their oomph, as “torture” and “Groundhog Day,” with testimony covering the same material that had been widely reported over the last nine months, only in excruciating detail. 

The first witness of the day was Tammy Ross, who back in February was the acting jail director when Montgomery allegedly arrested her under dubious pretense, one of many actions that now also has Montgomery facing criminal charges in federal court. Ross said that the first time she met Montgomery she noticed right away he had “a look of arrogance, a look of entitlement” on his face. 

After well over an hour of friendly questioning of Ross by Goodwin, there was hope the happenings might get a little spicier upon Mason’s cross-examination. Mason, speaking to Ross, began: “I am basically going to talk about things we have talked about before.” 

Mason’s stated intent during his opening arguments was to discredit the witnesses testifying against Montgomery. He attempted to do so with Ross by impugning her credentials, going through her resume leading up to her arrival at the City Justice Center, including a stint at Rally’s. He listed a number of professional organizations she hadn’t joined whose conferences she hadn’t attended.

At one point, outside the courtroom, a trial attendee noted that if all of Montgomery’s alleged misdeeds get such a deep dive, his trial is going to last three weeks.

Things eventually did get heated between Mason and Ross, though any excitement was undercut by its subject matter being extremely in the weeds of jail policy and procedures. Said an exasperated Judge Stephen Ohmer: “The questions are getting convoluted—the answers, extremely so.” He added: “Don’t start rambling and we’ll get done.” 

As his second witness, Goodwin called Anthony Anderson. Back in January, then-deputy Anderson accompanied Montgomery as he confronted Darryl Wilson, a deputy Montgomery had fired but who Montgomery reportedly suspected was “impersonating” a deputy as he worked security at a south citygas station. The AG’s office says that Montgomery illegally took Wilson’s firearm as part of the confrontation, an action they say demonstrates how the sheriff, despite his limited mandate, was going around attempting to enforce criminal law. (Making that overreach worse, Montgomery is not himself a POST-certified law enforcement officer.)

Anderson half-heartedly applied for criminal charges against Wilson at Montgomery’s request. Reading between the lines of Anderson’s testimony, the veteran of several police agencies knew there was no way a prosecutor would take the case given Anderson had no police report or warrant application. The judge asked what charges Anderson had even applied for. Anderson was vague in his answer. A month after the gas station encounter, he was fired when comments he made to the media about it drew his boss’s ire.

His testimony was at times interrupted by severe back pain, which Anderson apologized for ailing him to the point of distraction. He said he’d skipped his medication that morning so he could give his testimony with a clearer head. It was hard not to feel bad for him. Many of the questions put to him by both sides were about the nuances of Wilson’s attire that day—the idea being to determine what merit, if any, there was to Montgomery’s accusations that Wilson was “impersonating” a deputy. At one point, Ohmer offered the witness a bottle of water.

Packing the courtroom alongside reporters and court watchers were about two dozen students from Ursuline Academy’s “You and The Law” class. Teacher Kevin Reid said he conducts these field trips regularly and his students always come away with some sort of insight. This trip just happened to coincide with the quo warranto trial to remove Montgomery. “There was a murder case happening down a few floors but it wrapped up,” Reid said. He said he didn’t expect his students would feel let down. “Beats the heck out of being in school.”

The class ducked out before lunch.