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HOME › HOWIE'S COLUMNS › TOM BRADY IS GOING TO BE SENTENCED TO PR…
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Tom Brady is going to be sentenced to prison tomorrow …

Howie Carr · Sunday, October 25, 2026 𝕏f✉
Convicted former Norfolk County Sheriff's Deputy Tom Brady. Norfolk County Sheriff's Office photo
Convicted former Norfolk County Sheriff's Deputy Tom Brady. Norfolk County Sheriff's Office photo

Tom Brady is going to be sentenced to prison tomorrow.

There! I thought that would get your attention.

Of course, there’s more than one Tom Brady in this world. For some Tom Bradys, this is the best of times, but for others, it’s the worst of times.

For Number 12, it’s just another Sunday — getting picked up in a limo from a luxury suite at the finest hotel in Detroit and then being driven to Ford Field to call the Packers-Lions late game on Fox.

For the GOAT, it’s the best of times.

"For the GOAT, it’s the best of times."

Then there’s the other Tom Brady, a 54-year-old hack from the other side of Norfolk County, Norwood. He’s packing his tooth brush today, getting ready to be sentenced in Courtroom 3 at 11 a.m. Monday.

The other Tom Brady has been convicted on felony charges of witness tampering and using interstate facilities to commit bribery and extortion.

The feds are asking Judge Julia Kobick to give Tom Brady 24 months in prison — two full NFL seasons.

Tom Brady is a hack’s hack, a payroll patriot for Norfolk County sheriff “Honest” Pat McDermott. When Brady starting giving Honest Pat cash ($3,500 in all), his pay skyrocketed from $103,000 in 2021 to $138,432 (plus detail pay) in 2024.

When Brady was finally terminated in May 2025, after months of “paid administrative leave,” Honest Pat handed Tom Brady a lump sum “leave/buy back” check of $81,992.66.

Professional courtesy… Democrats.

On Friday, I asked Honest Pat for a comment on his loyal minion, on the eve of his incarceration. The sheriff declined to comment.

Brady was a straw boss in Honest Pat’s hackerama. His title was “assistant deputy superintendent.”

He started forcing his underlings to work at his house, doing plumbing chores among other tasks. He paid them nothing. Sometimes they had to do Brady’s home repairs in their jail uniforms.

This is SOP in the hackerama, and Tom Brady comes from a extinguished, er, distinguished Norfolk County hack family. His brother-in-law, Brian Walsh, is a hack district court judge ($207,855 a year).

His wife, Jennifer, is yet another lifelong payroll patriot, a “chief probation officer” at the public trough for $167,038 a year.

In her pre-sentencing letter to the judge, Mrs. Brady said she “fell in love” with the other Tom Brady because “his dedication to faith and family.”

The feds laid out Tom Brady’s dedication to faith and family in their pre-sentencing memo. When the employees Brady was oppressing at the jail began dropping dimes on him, Brady fought back in the traditional hack manner.

He mailed out anonymous letters full of lies about them, trying to destroy their lives.

The feds described how he sent one letter to a local elementary school. It “described in graphic detail that (the victim of Brady) sexually molested his minor relative.”

Totally false, but it accomplished Tom Brady’s goals.

“The letter destroyed (the victim’s) family and his relationships. As for the minor relative — a child at the time in elementary school — after DCF (Department of Children and Families) interrogated her best friend and her parents about the contents of the letter, the minor relative suffered the loss of her best friend.

“Subsequent bullying resulted in the minor relative eating lunch alone in the school bathroom, and the minor relative lives in fear that new allegations will potentially impact her life.”

Nice guy, Brady.

You can see why Honest Pat would want to hand Tom Brady all those promotions and pay raises. The sheriff even put him in charge of the honor guard at the jail. Of course he did!

Here’s what Brady did to another worker he’d been shaking down. He sent an anonymous letter “with a condom inside, disclosing a relationship with another (jail) employee, to his parents…”

In addition to the condom Brady enclosed “a handwritten note, ‘Take Me Back or I will tell Your husband Love You.’”

The FBI dusted the envelopes containing the scurrilous anonymous letters for fingerprints. Guess whose they found.

Meanwhile, as Tom Brady faces justice, Honest Pat and his remaining crew continue to live the high hack life uninterrupted at the almost-empty jail in Dedham.

The sheriff has found a replacement for Tom Brady. His name is Robert Vitale, and his title is “executive deputy sheriff.” He just got a pay raise to $147,900.

In 2023, Vitale left an even sweeter gig in the hackerama, in the trial court. He pocketed his own “leave/buy back” kiss of $30,075.33, after which he parachuted into the House of Correction.

Lately, Vitale too has found himself on paid administrative leave. Despite no longer working, he’s retained his county vehicle, a Chevy Tahoe.

Honest Pat declined to answer questions about Vitale’s status.

(Note to Sen. Brownsberger, who’s seemed concerned about all the waste and bloat at these nearly empty county jails: Do you think hearings into all these paid administrative leaves and who’s getting them under what circumstances might be a fruitful line of inquiry, Senator?)

Then there’s Honest Pat’s counsel, Courtney Madden. She just got a big fat pay hike, from $116,000 to $150,000. She owns a dog, a St. Bernard named Brutus. Did I mention that the sheriff likewise owns a St. Bernard? His is named Cleo.

Don’t laugh — lucrative hack careers have been based on less.

Then there’s Samantha Dallaire, Honest Pat’s “chief of staff.” She used to be the hack flack for the former Senate president, Therese Murray. Sam pockets $165,000 a year, in addition to the Ford Explorer she drives back and forth to Plymouth on the days she shows up for work.

A car and free gas — that’s worth at least another 30 grand a year, on top of the hack salary. Honest Pat has a fully loaded Ford Expedition.

Don’t forget Frank Reynolds, the “superintendent” who’s gone from $163,240 to $173,000, plus OT and details, not to mention his own Ford Explorer. Does he have a college degree? I asked Honest Pat. No comment.

Read it and weep, Tom Brady. You too could still be slurping at the county trough, if only you hadn’t been such a rotten bastard.

Two of the people writing letters for him to the judge called Tom Brady a “glue guy.”

Indeed he was. He had very sticky fingers. He just should have put some gloves over them before mailing out those vile letters…

Tomorrow afternoon we’ll be running a headline, “Tom Brady Gets Prison Time.”

It’ll get more clicks than any other headline in the Herald this year. Guaranteed.

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HOWIE CARR HCRN columnist. Boston to the bone. More from Howie Carr →
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