TB Investigates

Barstool Sports Small Business Fund Gave Money To Plymouth Limousine Business Whose Owner Was Former MBTA Union Boss Indicted By AGO For Accepting Over $300K In Bribes


Dave Portnoy is currently doing God’s work at Barstool Sports by raising over $18 million and counting for small businesses who have been negatively affected by the pandemic. Meanwhile, all the critics who tried to get him deplatformed this summer because he sang Ja Rule lyrics in 2015 have given nothing and done nothing to help small businesses. To get money from him businesses must send him an email, explain their situation, and he doles out the cash. However, it’s not clear how this process works, which has opened the door for con-artists.

Yesterday Barstool announced they were giving money to a limousine company out of Plymouth called Special Occasion Limousine. Here’s the email owner Diane Dockery wrote to Portnoy:

My name is Diane Dockery and I own Special Occasion Limousine in Plymouth MA. Yes a woman owned business in a male dominated industry!  In 2009, after 22 years at my job my boss left his position which left me with no job, it was the beginning of the recession and I was having a hard time getting another job. So, in a stroke of genius I decided to open a business… during a recession….with no experience…… that was fun. But Plymouth is just far enough away from Boston that people don’t want to drive to the airport, so I decided a car service would be a good idea!!  Plus, Plymouth Rock Studios was set to open in Plymouth also and I was the only limousine service in the town at that time so I thought I was onto something big.

Plymouth Rock Studios never came to be, but with ALOT of hard work Special Occasion Limousine grew. We went from 2 cars to 33 cars (sedans/suvs/vans/limos/mini buses). I have worked every single aspect of this company (except for mechanical work) I will get out of my bed in the middle of the night if I get an emergency call from a client and do whatever needs to be done. The first 5 years I didn’t collect a paycheck, but around 2017 my company really took off!!  I have a great client base, many clients are on a first name basis with me and when they call in we play a little catch up on each other’s lives before we get to the business of the reservation.

My staff is amazing, my operations manager has worked for me for FREE since March when the pandemic hit.  YES I SAID FREE. He is amazing and so wants us to survive this pandemic.  My drivers are like family to me, and many of them have worked for me for years, a few from the very beginning.  I have very little turn over on staff.  They count on me and I count on them.

Anyway, I am down 90% in my business and I’m hanging by a thread as of now.  I’ve lost over $850,000 this year compared to last year.  My funds are totally depleted after a very long 10 months.  The work isn’t coming in but the bills are.  This past year I lost all proms, all concerts, all sporting events, all bachelor and bachelorette parties and almost all weddings.  My airport work went from 50 jobs a day on average to weeks of no jobs at all, we are now at around 5 jobs a day.  My staff is on my payroll and has been.  But without some help I don’t know how much longer I can stay open.  Car loans, car insurance, workers comp, rent for my business location, all these things keep coming in.

I could very much use some help, its tough to ask for help when I’ve always been self sufficient all along so forgive me if this rambles. Thanks for your time, and God bless you for doing this.  Even if I don’t get picked, its awesome to watch the videos of those who do because I know exactly how they feel and seeing the relief in their faces is amazing.  I am pretty sure my video is attached below…. I hope, lol.

Happy New Year.

Diane Dockery

The “female business in a male dominated world” pitch worked well for her, since he mentioned it was why he was choosing her.

Diane’s husband Tim Dockery is a big supporter of her business on Facebook.

At a board of selectmen meeting last year he was listed on the agenda with his wife as a representative of their business.

I only bring this up because Tim Dockery was indicted three times by the Attorney General’s Office in 2017 and 2018 for being a corrupt political hack for the MBTA.

On February 26, 2018, a Suffolk County grand jury handed down additional charges against a former Massachusetts Bay Transportation Authority (MBTA) procurement official. The indictments, which resulted from a joint investigation by the Massachusetts Inspector General’s Office (OIG) and the Attorney General’s Office, allege that Timothy Dockery, 51, of Plymouth received over $200,000 in illegal gratuities from a construction company that performed work for the MBTA.  The indictments further allege that the same vendor also paid to install an in-ground pool at Mr. Dockery’s home.

In March 2017, Mr. Dockery, a former buyer for the MBTA, was first indicted for procurement fraud, larceny and receiving more than $90,000 in illegal gratuities from MBTA vendors. (See OIG Joint Investigation Leads to Indictments of MBTA Procurement Official and Construction Contractor, March 2017.)  In June 2017, Mr. Dockery was charged with additional counts of fraud, bribery and illegal gratuities involving two additional MBTA vendors.  (See Additional Indictments Brought in Case Against Former MBTA Procurement Official, June 2017).

Mr. Dockery is charged in the new indictments with two counts of accepting illegal gratuities. Taken together, the three sets of indictments allege that Mr. Dockery received over $300,000 in bribes and gratuities.

He accepted over $300K in bribes and got a free pool out of it.

He was also the management’s union President, and kept working in that capacity despite the first indictment.

THE PRESIDENT OF an MBTA union is facing charges that he used his position as a buyer for the agency to submit fraudulent invoices that netted him more than $100,000 in cash and kickbacks, according to Attorney General Maura Healey’s office. Dockery, who has been on leave from his buyer’s job while serving as union president, was suspended when the indictment came down. His buyer’s job gave him responsibility for procuring and overseeing contracts related to non-inventory items, such as office supplies and smaller construction contracts.

“The criminal conduct alleged in this indictment by the head of the T’s largest management union is very troubling, and it strengthens our resolve to continue bringing reforms to the organization,” acting General Manager Brian Shortsleeve said in a statement. “There is no evidence to suggest that any other MBTA employees were involved in the alleged wrongdoing.”

According to prosecutors, Dockery, 50, had a deal with one vendor to help him with procurements and projects and, in turn, Dockery received at least $60,000 in kickbacks off contracts worth more than $1.8 million since 2011. In addition, Dockery allegedly submitted phony invoices totaling $38,000 for money left over in procurement contracts and split the cash with the vendor. The unnamed vendor, who was not indicted, has entered into an agreement with the attorney general’s office to pay back his half of the stolen money, prosecutors said.

In the procurement fraud scheme, prosecutors claim Dockery created fake quotes to make sure Sheridan was the low bidder on a construction supplies contract. Dockery allegedly inflated Sheridan’s bid so that it was just under the fake quote and “created the illusion of a competitive procurement process,” according to the attorney general’s office. Sheridan also allegedly created and submitted fake quotes from other non-existent companies to ensure he was the low-bidder on another contract.

Some might argue that her business should not be associated with his crimes, however her business also benefitted as part of the bribing process.

Prosecutors also allege Dockery received more than $30,000 in illegal gratuities from two other unnamed vendors, including high-end sporting event and concert tickets, lunches, and goods for Dockery’s private limousine and coach business.

This happened in 2017, the same year she said her business “really took off” in the email she sent Portnoy.

“The first 5 years I didn’t collect a paycheck, but around 2017 my company really took off!!”

On top of that, in 2016 Tim Dockery was listed on the Secretary of State’s website as Vice President of Special Occasion Limousine.

After being indicted in 2017 he was removed.

But they’re still together, he’s still actively involved in the business, and is clearly a silent partner.

It would appear Dockery’s scheme was organized and pre-meditated. He used his position to enrich himself and his friends, and although at this time we’re unable to find any records of a disposition, the mere fact that he was indicted three times speaks volumes. I reached out to Diane for comment, but she would not provide an answer because the public indictment was personal.

She claims her husband is not involved in the company, but he was prior to the indictment, he will benefit from the funds, and as recently as 2020 he was acting as a representative for the company at town meetings.

Apparently all you have to do is send Dave Portnoy an email and he seems to just randomly pick who gets $500K.

Are there not more deserving businesses than this one? He might as well have rang a dinner bell for every crook and con-artist if all he requires is a girl power email to get the cash.

Additionally, he said that businesses are only eligible if they pay their employees throughout the pandemic. But Diane herself said in the email that one employee was working for free since March.

My staff is amazing, my operations manager has worked for me for FREE since March when the pandemic hit.  YES I SAID FREE.

Does anyone actually believe that an employee voluntarily didn’t collect a paycheck for 10 months? Is Tim the operations manager? I feel like these are questions that should be asked before handing out half a million in cash.

Dave Portnoy’s heart is in the right place and he should be commended for what he’s doing right now. In many ways he is a victim here. But at the same time when you raise $17 million and counting you have a responsibility to make sure you have a solid vetting process so that you’re not handing money over to criminals just because they pulled the “woman owned business in a male dominated industry” card. If you donated to this fund would you want it going to Tim Dockery’s legal fees? If you’re going to do something like this, then do it right. Hire a board to oversee the process instead of putting out feel good videos about girl power.


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