Patrick Dolan
Charles Dolan's son
13
APPEARANCES
3
PODCASTS
012
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Oct 24, 2026
The Cubs Win The Latest Round In Their 20-Year Battle With The Rooftops
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6:01Patrick DolanGUEST
So most states do not require employers to pay their employees to serve on juries.
Let’s Get Legal: Can holiday PTO be denied?
1:04
11:50
Jon HansenHOST
First of all, can you just walk us through PTO and holiday requests? Are there any laws about what companies can or can't do in terms of how they determine who can get it and who can't around the holidays?
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1:17Patrick DolanGUEST
So generally speaking, employers in Illinois can legally deny PTO and paid leave requests, but they got to follow specific state rules and they have to have written company policies about that.
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1:32Patrick DolanGUEST
So what are the reasons they can do it? So if employers have a legitimate business need, that's one of those, you know, legal phrases that folks argue about all the time.
P
1:43Patrick DolanGUEST
They have a legitimate business need that has to do with staffing needs, particularly on peak seasons, such as holidays and high volume periods.
P
1:53Patrick DolanGUEST
They can, based on policies that they have made available to employees, deny PTO requests for those legitimate business reasons.
10 MINS LATER
Jon HansenHOST
Talk us through the legalities and any potential pitfalls as we get towards holiday bonus season.
Will 'Broadview Six' Prosecutors Be Disciplined?
20:18

Mike LeonardGUEST
But Patrick, you talk about all the problems we're, we're, we're gonna face here and why you don't think this is ever really gonna happen.
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20:24Patrick DolanGUEST
I mean, I think you have so many different issues and so many different parties pushing and pulling in different directions.
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20:30Patrick DolanGUEST
The thing that I think may make a difference though, Mike, is if conferences are actually given the ability to make rules and enforce those rules, I think that's the start of something, and then you may see conferences like the Big Ten or whatever issue what we consider to be c- a cap.
Is Congress coming for college sports?
M
21:16Michael LeonardGUEST
But Patrick, you talk about all the problems we're going to face here and why you don't think this is ever really going to happen.
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21:22Patrick DolanGUEST
I mean, I think you have so many different issues and so many different parties pushing and pulling in different directions.
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21:28Patrick DolanGUEST
The thing that I think may make a difference, though, Mike, is if conferences are actually given the ability to make rules and enforce those rules, I think that's the start of something.
34 MINS LATER
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55:37Michael LeonardGUEST
i've never seen that's funny i've never seen that that approach where you had a piece of paper you wrote that out or a paper bag not a bad idea not a bad idea um i'm not sure if it's always necessary but i wouldn't i wouldn't uh fault it i would fault patrick for You know, me bringing him a sandwich and him not eating it, that to me is a bigger
The Illinois End-of-Life law that has families, doctors and faith leaders asking: Where is the line?
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16:02Patrick DolanGUEST
Listen, I'm typically the cynical person, Mike, as a plaintiff's employment lawyer.
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16:08Patrick DolanGUEST
But I think because the decision is made by two physicians, health care practitioners, I think that's sufficient safeguards.
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16:23Patrick DolanGUEST
I look at it a little bit differently as someone whose father died within the last couple of years who suffered.
12 MINS LATER
The Last Minute Push To Stop Illinois' Aid-In-Dying Law
7:53
16:12

John HansonHOST
I think that Mike and Patrick can, Patrick can in here, too, the idea of I think so many people have seen and gone through, maybe their parents or their grandparents or aunts and uncles suffer with some debilitating diseases, and I think that has been what has really changed people's hearts and minds, is as we live longer and sometimes live with diseases longer, the calculus on this has changed, Patrick.
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8:15Patrick DolanGUEST
Yeah, I think this is one of these examples where the law's catching up to where people are.
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8:19Patrick DolanGUEST
You know, Dr. Kevorkian, as Mike pointed out, all those issues were back in the '80s, and frankly I think for some people it really shocked the conscience.
P
8:25Patrick DolanGUEST
What we didn't know at the time was he was ahead of his time, and frankly, what he was doing was, was, uh, in not, not new in a number of places in Europe, specifically Switzerland, which people always point to.
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8:37Patrick DolanGUEST
So I think there's been a lot of support for this, uh, generating, uh, generated over maybe the last couple of decades.
P
8:49Patrick DolanGUEST
You know, it's absolutely heartbreaking and horribly difficult to see a loved one go through the end of their life suffering for months and months when everyone knows that their life is gonna end within, you know, six, nine, 12 months.
7 MINS LATER

Mike LeonardGUEST
... what happens in this situation, Patrick, in terms of death and death benefits?
Turns Out You Can Be Discriminated Against At Work. Here's How.
15:31
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2:56Patrick DolanGUEST
They try to, and oftentimes they would prefer that someone be a consultant because then you don't have to provide benefits.
P
3:06Patrick DolanGUEST
A lot of benefits, frankly most if not all benefits, don't go to consultants.
P
3:11Patrick DolanGUEST
And so oftentimes employers try to slot folks into consultant or independent contractor positions when frankly they shouldn't be because they control what that person is doing.
P
3:23Patrick DolanGUEST
when they're doing it, how they're doing it, whether they're getting paid for expenses, when they show up, where they work, all those sorts of things.
12 MINS LATER

John HansonHOST
I mean, that's the reality is I think a lot of independent contractors just go along with the game because it's the way the game is played.
Is The American Justice System The Best? An Outsider Weighs In.
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8:22Patrick DolanGUEST
So right now, because your podcast is successful, you're going through a whole bunch of different possible stories to put on the air.
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8:32Patrick DolanGUEST
Is there a common thread that you looking back that you think, oh, this is what you know, why I've picked this case or going forward? Is there something that you sort of look to? Because I imagine a lot of folks who've been convicted and incarcerated say that they didn't do it.
11 MINS LATER
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19:53Jack LaurenceGUEST
And then the cop ended up slipping up on the stand during an evidentiary hearing and it was discovered that he'd lied the whole time and he also paid the informant as well, which he said he never did.
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20:02Patrick DolanGUEST
You know, you mentioned earlier something that you learned in that Michigan case, which I find interesting as someone who watches true crime podcasts and TV shows like a lot of people do.
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20:13Patrick DolanGUEST
Do you think there's a distinction between the fairness of the process in rural America versus urban America? You talked about the relationships.
50,000+ Laws Have Been Passed In American History. These Are The Best.
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7:44Patrick DolanGUEST
And this is going to be something, John, you might nerd out about a little bit.
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7:47Patrick DolanGUEST
So I thought, what are the most consequential acts to support the American worker or impact the American workplace from each of the three branches of government? just one act one for each one one for each one so i've got one for the judiciary which is the supreme court in this case okay the congress and the president
11 MINS LATER
Sidebar: The Pope Is Critical Of AI, So Can You Stop Using It At Work?
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5:47Patrick DolanGUEST
Now, remember, this isn't like people who have political problems or personal basis not to use.
Episode 178: Cannes Fashion Choices, Plus Patrick Dolan on the State of OOH Advertising
45:24
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41:08Patrick DolanGUEST
You know, well, that was, uh, one of the reasons why we engaged the Winterberry Group to do this study that I, I was telling you about.
P
41:18Patrick DolanGUEST
You know, there are retail media networks that are going into stores, right? So you've got thousands of screens, you know, as far as Walmart is concerned, and other retail media, um, companies that are out there.
P
41:32Patrick DolanGUEST
And then, of course, you got your neo-retail surrounding the, uh, retail screens and the CTV and digital billboards and things like that.
P
41:40Patrick DolanGUEST
And I- marketers see that as a huge opportunity to, again, go through the path to purchase and, you know, be able to create a message, you know, through that path.
P
41:54Patrick DolanGUEST
The, I think the challenge right now, and what I think the opportunity is, is, like, how do you connect those two together? And doing that with, you know, programmatic capabilities just seems very logical to me.

Ari PaparoHOST
Um, are you seeing similarities? Is this, is this just a phase, or is everything gonna change forever?
Sidebar: Will US Attorney Resign? + Many Chicagoans Fall For New Scam
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10:15Patrick DolanGUEST
So, um, w- uh, un- unless the information is being used by someone in your position to impeach, uh, someone who provides testimony to the grand jury, why should you get that information? It's not evidence.
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10:27Patrick DolanGUEST
What do you, why do you want it other than you just want to know what's gone back and forth? And if the judge has an oversight role, which they do, then why don't you just let them discern? In other words, why do you think you should get that information? I don't think you should.
8 MINS LATER
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18:26Patrick DolanGUEST
So they'll give you 50 bucks, they'll give you 100 bucks, they'll give you whatever it is, but you never quite get that 500 bucks back.
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18:34Patrick DolanGUEST
You take on more tasks and give us more money so you can exceed the 500, and that's so you can exceed the $3,000.
Sidebar: Charges Against ICE Agents? + How AI Discriminates Job Seekers
20:08

John HansonHOST
Uh, are you saying that there has to be a human in the loop? Is that like the, the, the phrase that law uses or is trying to use to make sure that, that the, the AI hiring process isn't as discriminatory as humans are?
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20:22Patrick DolanGUEST
What the law is doing in Illinois and California and in c- other cal- a couple other places like New York is making sure that if company uses AI to hire folks, which just about every company does now and has for a while, but now it's really explicit, to kind of go through the applicant pool, weed them out, determine who should be interviewed, uh, determine who's qualified, et cetera, et cetera.
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20:55Patrick DolanGUEST
Now they're saying, the law is saying HR folks must insert themselves into that process to ensure that it's not discriminatory, not just in terms of sort of what you put in to ensure what you get out, but look at the result.
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21:09Patrick DolanGUEST
If you're getting a bunch of candidates who are always under 40 or always white or none of them are disabled, uh, et cetera, in other words, all those categories that we think of that are protected by employment laws, if you're getting, uh, none of those folks, then there's gonna be something wrong with your hiring process in terms of who you're vetting out.
10 MINS LATER