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Town manager deletes texts related to hiring; Natick’s Lt. Cara Rossi chosen for Ashland’s Police Chief, a month after the date promised. Requested records released after pick made.

- January 29, 2024 - Frank Wood

Interviews were conducted in March and April 9th the decision between Santiago and Rossi was expected. That day came and went. Michael Herbert the town manager claimed that they were doing background checks on both candidates and after that was done – a decision could be made.

But should we really trust a town manager who deleted public records, claiming that he didn’t know he was really deleting public records.


Was it really – a background check??? Or was there an incredible amount of internal strife going on…. and based on what you will see in this post – was the right decision made? We find it suspect that merely days after announcing Rossi as the new hire, that they would release documents to us that would lead to the public second guessing their town leadership….

In this first email by Hebert – we learn about the finalists and the contingency of a background check – however the background check seems pretty standard and routine.

Jennifer Ball, on the email above, gave some thoughts.

Prior to the announcement of finalists – a Sergeant in the Ashland Police shared some concerns and wanted to talk to Herbert.

It appears the two did not touch base, and the Sergeant put his thoughts in writing.

In this first email – the author relies heavily on our quality research – see the attachment list. This message was sent to everyone – including every member of the Ashland police department.

In other cases – support is heavily for Rossi based on knowing ‘Cara pretty much my whole life’.

Herbert responded positively.

It is apparent that there was some accusations of impropriety – after FU started digging in, and our initial requests showed that well before the job was posted, that Town Manager Hebert and Cara Rossi were talking about the position. December 1st, Rossi knew about the upcoming job posting and reached out to Herbert. In Herbert’s response, a few days later, he expressed concern that he should be writing Rossi at all about this matter, as he writes “I am not sure if us meeting would be the best thing for the process”.

It wasn’t a secret that the town was going to start looking to hire (11/2/2021 Facebook post below) – however the job has not been posted yet.

We do know from the evidence below that it was not until the end of January that Rossi applied for the job.

Did they meet prior to the job being posted? We are investigating it. While Herbert has made it apparent that he deletes public records – we have call and text logs for some of November and December – however some of the numbers are redacted for unknown reasons.

There are no numbers listed showing that Rossi called or texted Herbert, but we only have a couple weeks of records and Herbert deletes public records.

So on the impropriety end – we are investigating…. and apparently people on the search team, employees of the town, and residents were also second guessing if this process was done in an honest and transparent manner, with a email from Peter Chisolm, suggesting that “when the search started, everyone knew who was going t get it.” The email was forwarded up to Herbert – who was upset by the accusation.

Chisholm wrote an identical message a few minutes later to Select Board member Steve Mitchell with and additional line – saying that everyone knew what the outcome would be.

In response to the original message sent to Brandi- she kicked it up to her boss.

On another tangent on this thread, Steve Mitchell – Select Board member – forwarded the initial message from Chilsolm to Herbert, and Hebert responded in a dismissive manner.

This wasn’t Chisholm’s first letter of concern to the town administration. He wrote one a couple weeks prior.

To that message – Herbert wrote back two words.

Another email came in sent directly to Herbert from a person who was concerned about a few Natick Unfiltered posts, as well as a bunch of our research and reporting, and the message merely contained copies of the posts.

Mr. Herbert,

After watching the interview’s I’m left with more questions than answers. Is Ashland hiring a Social Worker or a Human Resource Chief ? I didn’t hear a single response about how the Laws of the Commonwealth are going to be enforced, how criminal acts will be investigated, or how the safety of the public will be ensured by the POLICE CHIEF. Is the Opioid problem in Ashland really that bad ? It’s my understanding that it’s not and when there is a police response it’s usually followed up and mitigated by the Fire Dept. correct ? Lt. Rossi stated she was in charge of Operations in Natick and now she’s the Public Information Officer ? In the Law Enforcement community that’s considered a demotion. You asked, “What’s your biggest mistake? Answer: “Wearing my emotions on my sleeve”.

That’s a perceived character flaw, not a mistake. “What do you know about the Ashland Police Department ?” Answer: “There’s a lot of traffic”, “They keep us safe”. And last but not least, Accreditation. That’s at the front of the line ? Maybe start with knowing the Ashland Police Department Mission Statement.

The claim is it’s the only place Lt. Rossi wants to be Chief. She grew up and lives here but seems to know very little about the it’s operation, its members or the residents she’s to serve.

With that said I’m compelled to provide you with some supplemental information which was easily obtained on the Internet.

Some may call it, “Fake news.” In my opinion all this information raises serious reasonable doubt that warrant’s extensive investigation to confirm or deny Lt. Rossi’s veracity. The concerns are three dimensional. Either way, the optics are bad…

This is inside information privy to and revealed by the Law Enforcement community. I say revealed as opposed to leaked because it’s obvious someone on the inside in Natick is willing to do the right thing and reveal conduct that is at a minimum unbecoming that of a ranking officer, some would argue illegal. As we learned with the past events in Minneapolis, action and inaction are equally condemned. Either way, this behavior is not consistent with that of a potential Police Chief.

It’s my understanding there was a lengthy build up by Lt. Rossi to reach today’s interview. It would be easy to allow that build up to cloud the decision making process. Truthfulness, Ethics and Morality (among many others) are minimum standards. It appears there is an attitude of being, “Above the law”. This idiotology is very concerning.

Within the law enforcement community it’s rumored Lt. Rossi is not being considered for the potential Deputy Chief Position in Natick ?

Something to consider is the potential among the existing members of the Ashland Police Department and future aspiring, “New” Officers to legally challenge the town if passed over for promotion or passed over as a new hire based on any past disciplinary action(s) taken or discrepancies during a background investigation. (this is supported by Case Law within the Commonwealth) To put this in simple terms, the defense will be, how can I be passed over and or not hired for having done this or that when the Chief of the department did the same or worse and is now Chief ?

Perhaps it’s best that the problems in Natick stay in Natick.

Chief Santiago should under go the same extensive background check.

Tho nervous and un-polished I felt he was sincere and displayed a combination of leadership and humility. I think he has a better understanding of leadership and an ability to manage a budget and understand diversity. His expectations/goals were realistic. He seems likeable and more apt to spend time in his office than bother you in yours….

Sincerely,

Concerned Taxpayer

On April 2nd, Herbert and Rossi worked to set up a meeting. This meeting was not unique to Rossi. Herbert also met with Santiago.

But Herbert didn’t want to meet in Ashland, perhaps he didn’t want anyone to see. He wanted to meet in Natick. Rossi and Herbert are residents of Ashland, so his suggestion that they instead meet in Natick is a bit suspect.

For full disclosure of the data – Herbert sent an identical message to Santiago.

And identically – Herbert wanted to go out of his way to meet Herbert, rather than meet locally.

Herbert & Rossi met at Sweetwaters Cafe in Natick, and Herbert & Santiago met at the Dunkin in Shirley. Santiago was meeting with the Shirley town administrator prior to the Dunkin meeting, and offered that Herbert meet him in his office – which was declined – it seemed that Herbert wanted these meetings to be under the radar and not in government or police offices.

The background check was expected and standard. On April 6th – the town got authorization from Rossi to look into her history. This background check wasn’t the issue.

Further digging has revealed that the “background checks” that were delaying the decision process could have been the Massachusetts Commission Against Discrimination (MCAD) suit filed against Natick Officer Quilty, Rossi, and the town of Natick. As we see – Herbert trying to get his hands on what it was all about.

Here are some more emails from the public on the Chief search. Click to enlarge the pages below.




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  1. Pingback: Ashland’s Police Chief Suspended. Is Rossi under POST Commission Investigation? Is she Brady List imminent? – This is FU

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