The Art of The Deal: Negotiating With Bob McCown

The room is on the fifth floor of a building in a bustling office complex. The buildings rise high above a traffic choked, pedestrian soaked neighbourhood in downtown Toronto. These buildings are referred to by their daily inhabitants as The Campus. A man, wearing tire black coloured sunglasses, sits in the fifth floor room and talks. He talks so eloquently, and with such hardihood and verve that the owners of these buildings pay him to talk. They pay him to talk in this room, known to all as “The Studio,” for three straight hours, five days a week. He’s been paid to do this for more than forty years. They pay him to talk into a silver mesh and wire microphone. His words shoot instantaneously through bundles of black and grey cords and copper wires that snake under the studio’s blue carpet, through the building’s floors, walls and ceilings and then are propelled with electromagnetic magic throughout the city of Toronto, to the east and west coasts of Canada and pockets in between. The Campus owners love it when he talks. They’re practically get giddy when he does. His baritone voice and peacocky word selection makes their media operation a lot of money. They need him talk. Badly. There’s only one problem: the man in the black sunglasses knows it, and the timing is good to posses such knowledge because it’s contract negotiation time.

Bob McCown, the host of Prime Time Sports on the Fan 590 in Toronto, wears his black Serengeti sunglasses everywhere apparently, bucking the widely accepted societal rule about never wearing sunglasses indoors. He wears them while on the air, he wears them during wedding receptions, and yes, he even wears them when he negotiates his work contracts.

McCown’s latest contract ends at the end of December, but by all accounts, he’s about to sign a three-year extension with Rogers, the powerful Canadian media and mobile corporation. McCown’s future was the source of much speculation this year. The way McCown talked on the air, and to close friends, you never truly knew exactly how this would all play out. He suggested at times that he’s done with the show, and radio in general. Perhaps the talk was all just another negotiating ploy. When you ask around, industry people rave about McCown as the master negotiator, poker faced until ink kisses paper. His negotiation skills, like the man himself though, are a cocktail mix of myth, legend and actuality. I’ve attempted to sift through the brume and fog to find out what makes him such a skilled negotiator.

Always Negotiating

“Everything (with Bob) is a negotiation,” said Don Kollins, one of four former Fan 590 program directors. “From what time are you showing up to your shift, to who are the producers, to who is the co-host, to, ‘When am I going to be on TV? How long am I going to be on TV? How long am I going to be on radio?’ He is sly,” Kollins said. “He is smart. He has a face like a stone when you’re negotiating with him. You never see him smile. And, of course, he has the glasses on all the time. So, you never get a chance to look at him in the eyes.”

The Fan’s very first program director, Allan Davis, said he and McCown were constantly negotiating. “It was everyday,” Davis said. “(Bob) loves the exercise. He loves the process of negotiating agreements. It’s what he’s all about. It’s one of the reasons why I’ve always said he’s so good at what he does because he has a business perspective on everything. He wasn’t up for, ‘Here’s the boiler plates, here’s whatever the terms are, sign it and away we go.’ He was about getting creative and trying to find ways to leverage things.”

The 65 year old McCown has done so many deals over the years that he feels supremely confident in the process. “I’ve done a fair bit of research and homework and read a bunch of stuff about the skill of negotiating,”McCown told me. “I came up with a formula that I’ve used over and over and over again. Obviously it changed and evolved over the years. You get smarter at things. You realize some stuff doesn’t work and some stuff does work. You learn from each process.”

It’s widely understood that McCown is constantly in negotiation mode. “Everyone knows this, it’s publicly known, he’s always negotiating,” said former Prime Time Sports producer Mike Gentile. “That narrative is always alive. Bob and his contract, it’s constantly a topic of discussion.”

According to McCown, negotiating his contracts are generally long drawn out affairs. “I have often said, it probably takes on average about six months to negotiate a contract,” McCown said. “If you talk to (President of Sportsnet) Scott Moore or (former Fan 590 program director) Nelson Millman, I’ve heard them say this when I was in their presence, that negotiating with me is like an experience they don’t ever want to go through again. It’s not because I’m an asshole, it’s because I’m persistent.”


I spent the first four and half years of my sports media career patrolling the halls and the carpeted, air sealed radio studios at 40 Holly Street in midtown Toronto, the original home of the Fan 590. I produced Fan talkshows at all hours of the day and night during my time there. There were late nights with Stormin’ Norman Rumack, mid mornings with Mike Hogan, and Steve Simmons, and afternoons with Gord Stellick. I spent one miserable week working the morning show with Mike Hogan and John Gallagher, while John Derringer and his producers were away on the vacation. It wasn’t a miserable week because of the guys I had to work with. Mike and John were a lot of fun. It was just that the hours sucked. I even got to spend a couple weeks producing Prime Time Sports with McCown. This was the pre-sunglasses era.

If you spent any time at the Fan, especially back in the early days, you heard the stories. Bob McCown’s contract negotiation stories. I always heard about a detailed list of demands or “wants” that he would send to management at negotiation time. I wanted find out if this list actually existed, and if it did, how he used it in negotiations and other strategies he used to to get what he wanted. And I really wanted to find out what it was like to sit across the table from him. That’s where this story was hatched.

As McCown grinds through the negotiation process, he tells me he constantly writes notes to himself. The notes consist of his own evaluation of himself, his status within the company, and candidates that Rogers could possibly replace him with. And he’s always trying to read the people he’s sitting opposite from at the table.

“Do you think they really give a shit whether they re-sign you or not?” McCown said. “It’s like reading tea leaves.”

One thing McCown stresses is patience, and having even more patience than those sitting across the table.

“We all want to do the deal quickly,” McCown said. “That’s the easiest thing. What I’ve always done is deferred the process. I never begin the negotiation. I never make the first phone call. Never ever ever ever. My contract is coming up? I’ll wait. Let them make the first move.”

When the company reaches out for the first time with specific details, McCown never responds.

“You just listen,” McCown said. “Don’t say yes to anything. Don’t say no to anything. Just listen. What they’ll do then is give you a blue print of what they want. You take it back. You think about it. And you analyze what you want and what you think you can get.”

McCown then attempts to prolong the negotiations for as long as he can. And yes, there is a “wants” list.

“I always had a theory that I’m going to put a hundred things on the table,” McCown said. “Out of those hundred things, I maybe want two.”

He doesn’t put all hundred things on the table at once. He’ll present the company with a list of ten things to start. They may reply telling him he can’t have any of them. He’ll then send a list of ten more things, and then ten more after that. He essentially tries to confuse them and wear them out.

“The longer it goes on, the more frustrated they become,” McCown said. “You can’t look at it as a battle, you have to look at it as a war, and a war is a series of battles. It could be five battles, it could be fifty battles. You don’t know how long the war is going to last. You have to be prepared to be there at the end.”

And all the while McCown says he keeps laser focused on those two particular things he really wants. He always gets them in the end. Davis said McCown cared about every aspect of the agreements.

“He took great time to consider every part of an agreement and what that meant,” Davis said. “He is also smart and astute and understood both ends of it. The front end and the back end. The back end being the other language that provides outs for people. He understood both. He was also astute, even early on, in terms of what his value was and the leverage that he could bring to a negotiation because of that value.”

Bob Mackowycz, Sr. took over for Davis as the Fan’s Program Director in 1994. “A lot of people think (McCown) has a certain kind of personality. I never found anything like that,” Mackowycz, Sr. said. “There was no vanity shit. He wasn’t a primadonna. He was very, very confident in his abilities and he was very confident in his ability to deliver the mail. He didn’t need velvet mic socks. I think he kind of knew he was in the driver’s seat.”

McCown says he doesn’t negotiate the actual money portion of the contract until the very end of all the discussions, and he always makes management play their cards first.

“Ultimately, the test is to get them to the point where they’ve gone through this so often, have had so many meetings, and so many back and forths,” McCown said. “They say ‘fuck it, whatever it takes.’ And when you get to that point, you always know when you do get that point, you know you got them. And that’s when you put your foot on the gas. And you say, ‘Alright, I want this, I want this, and I want this much.'”

Myths & Legends

One of the myths about Bob McCown is that he’s often prickly and crabby. He certainly plays that character on radio. He projects this image to great effect. It’s probably one of the reasons why he’s been so successful over the years. Whether he’s lamenting about a slow commute into the office on a snow-blasted Toronto day, or telling the Mayor of Hamilton, Ontario to shove it, the audience laps it up. His railing on station management has been a big part of his on-air shtick for years. Ranting on air about the “Suits” walking into his studio mid-show and interrupting things, or opining about how he’s going to clean their clocks come contract negotiation time, observers suggest it has endeared him to his listeners. Kollins couldn’t believe his ears the first time McCown brought up his contract on the air.

“I was scared as hell,” Kollins said. “I didn’t know what to do next because it’s Bob McCown. Sure I’m the Program Director. Sure I’m managing the station. Nobody manages Bob. Bob manages himself. Some negotiations did play out on air.”

“It’s all tongue-in-cheek,” McCown confessed, “but there’s truism in it. I don’t do it without an agenda. I just try and be honest. I don’t have much of a filter.”

The on air barbs didn’t seem to faze Millman.

“It used to make me laugh,” Millman said. “It didn’t matter. So what? So he’s talking about his contract on the air. That’s Bob. All the names and everything else and all the things he said…I always just laughed. Unless it was something confidential which I don’t ever recall him doing. So if he wanted to go on the air as part of his act and as part of the radio show, talk about the idiot program director. I was cool with it. It didn’t matter once you were in the boardroom. Howard Stern did the same thing. Was management scared by what he was saying on the air? Fuck no.”

Breakfast Flakes

Not long after the Fan switched formats to 24-hour sports, McCown was asked by management to move from his afternoon time slot and host the station’s morning show. The morning time slot was struggling so management thought it would be a great idea to move the station’s most popular host, McCown, to mornings.

“They asked me to do the morning show,” McCown said. “I said no. And I said no, not because I was negotiating. I said no because I didn’t want to do the morning show.”

Management pressed the issue. “They kept coming back to me, over and over and over again. I kept saying no no no.” According to McCown, a station executive asked him to go for dinner one night. The two met at a local Italian restaurant.

“(The executive) pulled out a paper and a pen,” McCown said. “(He) slid it across the table and said, ‘Write down what it would take for you to do the morning show.’ I said, ‘I’m not going to do that.'”

With the pen and paper now on the table in front of McCown, the two went back and forth, all while McCown explained he simply did not want to take over the morning slot.

“So, I thought about it for a second,” McCown said. “And then wrote down a number that I absolutely believed he would balk at. (The executive) looked at it for a second, and he looked me in the eye, and looked back down at the number, and he said, ‘Ok, done.’ My first thought was, ‘Oh fuck, too low!'” McCown spent two years hosting the morning show before being replaced by John Derringer.

Back To Prime Time

Dan Shulman took over as the host of Prime Time Sports when McCown moved to mornings. Shortly after McCown was bounced from mornings, it was announced that Shulman was leaving the station to call Blue Jays games on TV for TSN. Immediately, those of us at the station started speculating as to who would take over for Shulman.

According to McCown, the wheels were already in motion for him to move back to his afternoon time slot. The week after hosting his final morning show the station threw McCown a going away lunch. He found it odd that they would do that but he went anyways. When he arrived he quickly realized there were only station executives at the lunch, there was no regular staff there at all. McCown told me that as they were about to sit down to eat, one of the station’s top executives walked up to him and whispered in his ear, “This was a mistake, it shall be corrected.”

McCown quickly understood that to mean the executive did not agree with McCown’s firing from the morning show. McCown also quickly realized that all of sudden he now had all sorts of bargaining power to negotiate his new Prime Time Sports contract. They offered him the job and immediately started negotiations.

“I decided that every meeting would be at my house,” McCown said. “I would not go into the station. They would have to meet on my turf. I’ll bet you we had five, six, seven meetings and I just kept saying, ‘Nope nope nope nope.’ And eventually got what I wanted.”

Mackowycz, Sr. understood how important McCown was to the station.”(McCown) had a number in mind and we were in the business of keeping him happy,” Mackowycz, Sr. said. “We didn’t want to lose him.”

Knowing that he had the station over a barrel, McCown was going to attempt to play one more card in the negotiations. “I said, ‘If I’m going to come back, I’m going to come back on a Friday,'” McCown recalled telling the bosses. “I will work one day and then I will go on vacation for three weeks of paid vacation. And they had to agree.”

Vegas Baby!

Let it be known that Bob McCown was in Las Vegas before the big leagues were there. Long before the NHL’s Golden Knights, and well before sinister Oakland Raiders owner Mark Davis put a shovel into the desert soil. After settling back into his afternoon time slot, McCown actually hosted the show from Vegas during the winter months for five years in the mid-90s.

How the heck did the Fan allow that to happen? “For Bob (McCown) there was one thing that was important to him back then and it was important to me too,” said Mackowycz, Sr. “McCown and I always got a long as individuals. We both had a similar kind of attitude. There was a little swagger to the both of us. If you go beyond the dollars and cents, the thing (McCown) really wanted to do — he wanted to swing in the big leagues, and that would be the States. As good as he is, you kind of want to play on the big field. I like to play at that level as well.”

Mackowycz, Sr. wanted to show McCown that the company valued his aspirations beyond just the afternoon radio show. So, Mackowycz, Sr. devised a plan to pitch Sports Illustrated magazine on the idea of a daily one-hour syndicated radio show with McCown as the host. The last hour of Prime Time Sports would be dedicated to American sports. The two Bobs flew down to New York City to meet with the SI executives.

“It’s one of those moments,” Mackowycz, Sr. recalled with great excitement. “You’re in the SI boardroom and you’re pitching.”

It was McCown’s suggestion that they do the show from Las Vegas with the thinking that it would be an ideal place to land interviews with top US athletes. The thinking was that everybody likes to go to Vegas. The SI pitch went well, and they thought they had a deal. McCown headed to Vegas and bought a house. Ooops! The deal with SI fell through. McCown now had a house in Vegas but no American syndicated radio show to host.

“So we cut a deal whereby I would go down and do (Prime Time Sports) from Vegas for the winter,” McCown said. “So I would go down for four or five months and do the show from Vegas.”

Mackowycz, Sr. understood the technical nightmare of the host being in Vegas, while the show producers were back in Toronto dealing with a three-hour time difference. Remember, this was all pre-internet and cell phones.

“It is about your franchise player,” Mackowycz, Sr. said. “People used to say to me, ‘how the hell could you let him do that? How’s he going to watch the Leafs every night?’ I said, ‘He doesn’t watch the Leafs now. What’s the difference?’ I thought it was really important to keep him happy.”

Producer Chris Clarke figured McCown just wanted to avoid Canadian winters. “He said he was done or he was going to get his way and do the show in Vegas half the year,” Clarke said. “He was sick and tired of the weather. He didn’t like the cold. It was another negotiating ploy. His contract was up and this was a way that he re-signed a contract. So, he said, ‘I’m going to work in Vegas for six months,’ and they said, ‘Ok, no problem.’ This was before the internet. It (was) insane to think that could happen, but it did. We were faxing him articles from the newspaper everyday. I was asked my opinion on it. I thought it was going to be a very difficult way to produce a show and host a show on his part. He had a little studio at his house, which was basically a mixer, an ISDN line and a microphone. That’s the way he did the show.”

Walking Away

One of the most important aspects of being successful in contract negotiations is to simply have leverage over the people across the table from you. If you’re willing to walk away from the table, and from a potential contract, then you’re way ahead of the game. According to some, McCown has played the ‘I’m walking away’ card numerous times over the years.

“When you talk about negotiating power, he lets on like, ‘If it’s over, it’s over,'” Clarke said. “I think there’s no way, but then he’s done it before. Maybe not walking away from contracts, but he’s definitely been let go out of a contract, and it didn’t really seem to faze him. He’s also the first one to tell you, ‘I’m done. Yeah, this is the last contract. There’s no way they’re going to get me back.’ It’s negotiating through just talking to people, but people talk to other people, and people hear that he says these things and it gets back to management and management thinks, ‘Oh man, is this guy willing to walk away?’ And it gets him a better deal.”

Clarke recalls McCown using this tactic back in the 90’s. “I’ve heard this many times,” Clarke said. “Every time a contract is over, or coming up, he will tell anyone who will listen to him that he’s done. I’ve heard it many times over the years. I don’t know how many contracts he had in the 14 years I was there, but I guarantee you, I heard it every time that he’s done.”

McCown says you can’t just arbitrarily go into a negotiation with a willingness to walk away.You have to be willing to walk away at a certain point, McCown said. “But then again, you have to understand who you are, what your strengths are, the guy at the other side of the table what his strengths are. Truthfully, probably 999 out of 1,000 people should never take the approach of, ‘I’m willing to walk away,’ because it’s not a question about how good they are at their job, but what kind of job do they have? What you really want to ask yourself is, ‘Am I replaceable? Is there one other person that can do my job as well as I can do it? Are there a hundred other people or are there ten thousand other people who can do the job as well as I can do it?’ You have to be honest. So it starts with that premise. And most people fall into the ten thousand category. A few people may fall into the, ‘There’s a hundred other people.’ There are very few who fall into the, ‘I don’t know of anybody else who can do it.’ It’s not a question of ego, you gotta be honest with assessing where you are. If you get misled by the ego, then you’re gonna get called and then you’re gonna end up out of job and not able to get another one. I always felt as though, ‘If I lose this job over a negotiation, I can get another job.’ And part of that is because of the offers that you get.”

The Competition on Line One

Being willing to walk away because you have somewhere else to go, you have another job waiting for you, is true contract negotiation leverage.

“Look, I’m not telling you somebody called me every week,” McCown said. “That didn’t happen. But with some regularity, I got calls. I got network calls from the U.S., I got calls from major markets. I got calls from New York, Boston, Chicago, LA.”

Millman heard this frequently from McCown during negotiations.

“Yeah, sure. Absolutely,” Millman said. “If there was leverage there to use, he’d use leverage in the negotiations. Did it always make a difference in where we wound up? No. Did he always say it? Yes. Why not? Why wouldn’t you? In fairness, I have no idea if he was talking to them or not. So I would take it in as part of the conversation, as part of the information that you used to make your business decisions.”

Millman made a point to clarify that McCown didn’t actually use this tactic each and every time.

“When I say every time, I don’t really mean every time,” Millman stated. “It was part of the fun we have. ‘Oh these guys love me. Ok, great, well go.'”

Phil King was the President of CTV when Bell Media started putting together plans to start a Toronto-based all sports radio station.

“When TSN Radio was starting up (in 2010-11), I tried to steal (McCown) from the Fan,” King said. “I went to his house quite a few times. I didn’t know him that well, but I got to know him a little bit and remember going over there and trying to negotiate a deal. The problem was he really wasn’t free and clear from Rogers. So nothing happened to it, and (Keith) Pelley (President of Rogers Media) matched it.”

I asked McCown what he remembers about the TSN Radio meetings. “We actually had an agreement,” McCown told me. “We had a verbal agreement for me to go there. (My agent) Gord (Kirke) and I believed that I could get out of my (Rogers) contract and TSN didn’t. Their lawyers didn’t. Phil and (former Bell Media executive, and current Rogers executive) Rick Brace came to my house. It was in general terms in the beginning and then it got a little more specific and then it got down to negotiation. They wanted to launch sports radio and Phil said he didn’t want to launch it without me. And he said he wouldn’t launch it without me. So, we went through the whole process and we basically came to terms in the general sense on an agreement. Then they wanted to see a copy of my contract so we gave them a copy of the contract and they gave it to their lawyers. Ultimately it failed because of my contract situation.”

King felt it was well worth his time to meet and pitch McCown on joining the TSN family.

“Bob’s one of the most famous, and I would argue, high profile and profitable radio hosts,” King said. “You can probably count on one hand radio hosts that can literally generate advertising revenue on his show, his name. There’s very few in this country. He’s definitely one of them.”

Some people I talked to for this story suggest McCown would never leave the Fan because he knows he has it good there. Was meeting with TSN another negotiating ploy for McCown with the aim to land a big deal from Rogers?

“Bob’s astute enough to know, whatever deal he got from, I guess it was Keith (Pelley) at the time, I suspect (McCown) either let it out or people knew that I was talking to him, which tends to increase your value,” King said. “So, another really smart negotiator is (to) make sure you have a Plan B. I don’t know if I (and TSN Radio) was Plan B or Plan A and it ended up not happening. I didn’t ask. I didn’t know. But good for him.

New Deal

It could be announced as soon as this week that Bob McCown has re-upped with Rogers. The word is that it’s a three-year deal to continue hosting Prime Time Sports from 4-7p.m., Monday to Friday on the Fan 590 in Toronto and on Sportsnet. The questions I want answers to are, how soon after the ink is dry on the new deal does he begin posturing and leveraging for the next deal? Or will there be another deal? Stay tuned.