An Interview with The Star’s Gregor Chisholm

by mike in boston / @mikeinbostonemail


With the Raptors taking the city by storm and the Leafs being a lead story 11 months out of 12 your Toronto Blue Jays have flown under the radar for most of the last calendar year. The heady playoff days of 2015 and 2016, with their packed stadia and superstar personalities, seem like ages ago. 2017 and 2018 were seasons lost to dithering by Shapiro and Atkins, and 2019 finally brought an earnest rebuild and the harsh reality of losing 100 games.


We’ve banked a bunch of Jays items for the dog days of summer and will be rolling those out over the next few weeks. The first item up is an interview with The Star’s Gregor Chisholm. Gregor took over the Star’s baseball column from Richard Griffin who moved into the lead PR role with the team he used to cover. Here is our conversation.



Q: How did you get started in sports media?


GC: I started with MLB as an intern in 2007. Before that I was an intern at TSN, which was my placement from Ryerson. When I was at TSN I worked in the pit area behind SportsCentre cutting clips and writing scripts for hosts. That led to an associate reporter internship with MLB. This is what convinced me that I wanted to be on the “print” side of things. My degree was actually in broadcasting. But after working at TSN and seeing so many other people my age who wanted to be in front of the camera I saw that those jobs would be scarce. The other thing with the MLB job was that it was really hands-on. I was at the park and in the clubhouse rather than being stuck in an office. That fed the desire to be working as a writer. At the end of the internship I worked at the Toronto Sun for three years doing mostly desk work. When the Toronto job at opened up in 2010 they called me for an interview and I was hired later that year. 2011 was my first official season in that job and I was there until a few months ago in 2019.


Q: The MLB job is with a league-owned site covering the Jays. Who do you report to? 


GC: The site is run by MLB Advanced Media which has their own separate office in New York. They run the streaming and technology side of things. MLBAM has an editorial department as well. There is a club reporter in every city. They used to have associate reporters in every city too. There are columnists. So they run everything in terms of coverage and that is who I reported to. It’s very similar to a newspaper department. 


Q: Since you work for the league and not the team, how much freedom is there in how you cover the Jays? Do you get preferential access to management and players?


GC: From my experience there was no preferential treatment. I can’t speak to what goes on in other cities. I was on equal footing with all the other reporters. I never felt that Anthopoulous, for example, was more likely to return my calls because I worked for There certainly was a perception that I worked for the Jays and I would have to correct that every now and then. The way I looked at it as a result of my journalism school training was that reporters are supposed to be down the middle. Since it wasn’t my job to be opinionated I didn’t feel a lot of tension when covering the team. 


Q: If you were a reporter at a traditional paper you would have a colleague who would give opinions on the important stories. At MLB you don’t have that back-up. Does that change how you approach something like the Osuna story?


GC: I don’t think so. If I worked as a reporter at The Sun rather than MLB it still wouldn’t be my job to give an opinion on the Osuna [domestic violence] story. I would cover the story by reporting the known facts. That’s what I did at MLB that morning when the news broke. I wrote about the allegations. But I didn’t follow up with a personal opinion piece on what the Jays should do with his contract. I feel that opinion columns should be left to people who have paid their dues in the industry. I had a little space to give opinions on twitter and that was fine.


Q: Did they give you guidelines on how to use twitter?


GC: To be honest it was a bit of a grey area. I felt confident speaking my mind but in the back of my mind there was some hesitation. I would tweet about numbers or in-game analysis but wouldn’t go too far beyond that because my role was to report. It was certainly different than what I am doing now. But having said that I’m never going to be Mr Hot Take. I think there’s an important difference between that and a strong educated opinion. I’m only going to put out there something I believe and not anything designed to get a rise out of people. I think people tend to dismiss anything they disagree with as a hot take and that’s wrong too. You have to be able to back it up and stick around for the debate.


Q: Was there any concern about taking a newspaper job at this moment is media history?


GC: I was pleasantly surprised when the job was posted and obviously elated when I was hired. I’m really glad they are committed to keeping the baseball column. I was also happy for the additional freedom to speak my mind. I was ready for a bit of a change in my career. I know that not a lot of people have gone from online to print in recent years but I have no concerns about that. 


Q: It’s early in your new job as a columnist. Have you noticed any major differences since switching from being a reporter to being paid to write opinions?


GC: It’s a very different job. And to be honest it’s not a job I expected to do over the last few years. But after all the time I have put in on the beat I’m really glad to have the opportunity to speak out more. There were times when, for example, a columnist would write something that I wanted to debate or disagree with and I felt restrained due to my role. As I said earlier, I’m a big “pay your dues” guy. I grew up reading Bob Elliott and Richard Griffin and I have so much respect for those guys. I would not have been prepared to have a voice even a few years ago. It takes time to build up that confidence. You need experience seeing the game to back up your opinions. That helps a lot when dealing with the backlash when you write something. Especially with the social media aspect of it, but internally as well. My relationship with players and executives will change going forward since my job now is be more critical.


Q: I want to follow up on the point about paying your dues. We often see this when someone moves from being a single sport writer to being a generalist. How do you establish credibility with both your subjects and the audience? There’s going to be a gap because people aren’t used to seeing you in that role.


GC: I look at it this way. I have seen a lot of people come on to the beat over the last 10 years who didn’t have a lot of baseball experience but are really good reporters. They learned the job pretty quickly: if you’re a good news reporter then you’ll be able to make the switch to sports. But becoming a columnist is tricky … there’s not a lot of room to learn on the job because you’ll lose credibility. You can learn the reporting side relatively easily but you do need lots of specifically baseball experience in order to have solid opinions. You need to know the game but also the behind the scenes stuff. Like how agents talk, how different front offices work, how clubhouses are run … if you don’t have that knowledge then you’re not going to be a credible voice. 


Q: It’s an interesting conundrum for young people wanting to break in to the industry. If you grew up reading Bob Elliott then when you write a blog post or something for the school newspaper that’s the style you’re going to emulate. But obviously that person doesn’t have any of the experience to back up their opinions. 


GC: Yeah, and there’s a lot of nuance in how you write a story when someone has said something off the record. That’s the kind of skill you can only develop by talking to people who have something to say. I used to be the kind of person you’re describing. I was a huge baseball fan and was looking to break into the industry. A part of me was upset that I even had to go to journalism school. But over time I came to see how the background is important. The grind helps you get perspective. You also get experience when a player blows up about something you wrote. That happens even when you’re more on the news side. It happened to me when I was young and it definitely rattles you. We also get lied to a lot so you have to develop the ability to tell fact from fiction. And to determine people’s motives for telling you things. That’s why I am so grateful that I had the chance to learn in a reporter role before moving to being a columnist. All of that said, the Jays beat has gotten a lot younger in the last few years so it’s possible we are seeing a shift. 


Q: Everyone knows Rogers owns both the Jays and Sportsnet. As a reader that means I rely extra heavily on the other outlets to dig for the stories that I know won’t be coming from Sportsnet. Does that context shape how you approach your job as the lead baseball columnist for The Star?


GC: I don’t look at it that way entirely. I don’t think I would change my approach based on the market. I’m a firm believer in independent newspapers. Every media outlet has its own interests at times. TSN has the CFL. has its own stake. The papers are criticized for their political leanings. But for me covering sports I don’t really think about any of that when I do my job. I have the freedom to pursue stories and give my opinions on the team. I’m excited about that. And I recognize that this market has a gap right now with the departure of Elliott and Griffin. Those are the people I wanted to read, especially when things were not going well. I’m not there now but that’s where I want to get. When there’s a big topic going on with the Jays I want people to care about what I have to say. That’s the ultimate goal with a job like this one and a challenge given the person I am replacing. Additionally, I like a market – like Boston – where the media is not afraid to write stories that they know will lead to heat from executives or players. I take that as a sign of a rabid fanbase that wants all the news they can get about their teams. I’m not going to make stuff up, obviously, but there is definitely a need for people in my position to ask tough questions.


Q: Given that your new role comes with a new focus, do you have to explain the change to the players you cover? 


GC: I’ve had a few people already jokingly say that I have joined the dark side. In one-on-ones I have also told players about the new job. It’s more of a common courtesy. Especially for the guys in Buffalo. I spoke with Anthony Alford recently and told him that I’m now writing for The Star. But one of the benefits of a year like this one is that there are so many new guys that I haven’t really faced the issue of guys being used to certain lines of questioning from me and then being surprised that I’m asking different kinds of questions. I’m just starting to build relationships with a lot of the players. It would have been way different two years ago. A guy like Jose Bautista I would have definitely had more of a conversation with about my new job. On the management side, I happened to run into Ross Atkins in the elevator the day it was announced and he very nicely congratulated me on the job. So that was a quick and easy acknowledgement of the change. The day to day is really going to be the same even though the product is going to be different. It’s not like I switched to being a banker or something.


Q: Is it news when players have issues with the media?


GC: No. At least not every time. Griffin didn’t write a story every time Stroman cursed him out in the clubhouse. You need to be selective, especially when things happen behind closed doors. The [NAT FUCKING BAILEY] incident in Boston happened in public and there were some colourful quotes and that rightly became a story. 


Q: Sportsnet didn’t cover that so there is obviously room for interpretation on these boundaries.


GC: 100%. But there is a damned if you do, damned if you don’t element to all this. You don’t want to give the impression that you’re airing your dirty laundry or just trying to cut somebody down. I get what you’re saying though about interpretation here. It’s hard to know when a line has been crossed. 


Q: Sports media sometimes get stuck chasing the same story. How do you plan what you want to write about, both in the short and longer term? 


GC: That’s an interesting question right now as I’m still trying to figure that out. I’m toying with a few concepts for regular features. There’s also the scheduled stuff like the draft. But so much of what I now do is going to depend on what happens with the team. I’m not going to be reacting to games as much, but it will be reactionary to be sure. Once they start selling off then I’ll need to be writing about that. Lots of Stroman and Sanchez and Giles analysis. I know what you mean about chasing the same story and I’m really looking forward to the challenge of finding a different view.


Q: As a columnist you have the responsibility of, to put it crudely, telling people what to think. For example, the general fan wants to know whether Stroman’s social media commentary is a problem or not. That’s where the opinions of experts come in. How are you feeling about that?


GC: To be honest it’s mostly about trusting my instincts and experience. I’ve always wanted to think of myself as an expert in this field … you know as a kind of professional goal. And now as I move into more of a senior role that’s the trajectory I’m on. And I agree that it comes with responsibility since you are, as you put it, telling people what to think. But that’s not how I approach it. I would like to think that I have proved that I am reputable so far in one role and I now I want to prove that again to the audience in a new role. People will of course disagree with me but I want them to see that my points are well thought out. That’s really the most important thing to me. I want the reader to see my point even if they disagree. And that should all be there in the writing: yes, you’re taking a side but you should also be presenting both sides as well.  I’ve seen good columnists and I’ve seen bad ones and it can be easy to sit at home and come up with some take that will get a reaction. That’s never what I want to do. I’ll still be at the ballpark every day, facing people if I have written something critical. And I’m also looking forward to the positive stories too. 


Q: How much do you care about audience reaction to what you write? Some media are famous for saying “never read the comments/mentions” but I think this is pretty disingenuous. Everyone who writes cares what the audience thinks to a certain degree, otherwise you wouldn’t be in this field. You want people to read it and you want it to be good. What kind of interaction do you want as a columnist?


GC: One thing I have definitely gotten better at is ignoring the really negative comments. When I started I prided myself on responding to everyone. I think it happens to a lot of younger people. People appreciated it and I felt good about doing it, but the downside is that you end up engaging with people who are just looking to be negative. And that can have an impact on you. So I have become a little smarter about staying away from the people who are just trolling. I’m much better about laughing off the really nasty stuff. I’m not a big blocker on twitter … you have to say something really personal to get that from me. So I ignore more than I used to, but I don’t want to be someone who doesn’t engage at all. I struggle finding the balance still. I really enjoy doing twitter Q&As and have not had time for that recently. I want to get back to that. There are people with whom I’ve been interacting on twitter for 10 years now and that’s really cool. Another thing is that so many negative comments rest fundamentally on ignorance about the industry and how things work. But comments that are just differing opinions? Bring those one and let’s have the debate. You can also breed some loyalty in the audience that way. That helps the paper and helps me. Lastly, I want to engage with people in part because when I started out other people engaged with me. Bob Elliott responded to my emails when I was in Grade 10. 


Q: A common complaint from players relates to criticism from media people who are not in the clubhouse all the time. You’ve already mentioned the importance of being accountable to your subjects. How important is it in your new role to be in the clubhouse every day?


GC: Definitely I need to be there the majority of the time. One of the biggest lessons I learned from Griffin is about facing the music. He really believed in letting the players respond to what he wrote, especially when it was something unpopular. That’s an important part of the process. The vast majority of athletes will do that in a pretty respectful manner. It may start off heated but you can usually find common ground. Again, most of the players and management understand that you have a job to do. If you’re not there then, over time, those relationships will fall apart. So I’m not going to parachute in. I’m not going to be sitting at home. You need to be available for when people have something to say. Sometimes a player will make a snide remark and then it’s up to you to respectfully give them an opportunity to clear the air. You can tell when someone is upset. And sometimes they don’t want to talk about it and the snide remark is all they are going to say. And that’s OK too. They get paid a lot of money and dealing with the media comes with that territory. So I’m going to take the Griffin approach and handle things the right way. There may be some drama along the way but as long as you’re being fair then the respect will follow. I might upset one guy but there will be others in the room who will take note and see that I’m doing my job. Some guys will never understand what our job is but that’s the minority. You can’t change your approach just because some guys fly off the handle easily. 



Thanks to Gregor for taking the time. Follow him here. Two quick discussion points:


1) I especially liked his ideas about audience engagement. It’s a pretty big shift from how the older generation approaches their readers and followers. I’m not sure if that is due to a fear of social media or a preference for one-way communication with the audience. (See for example the people who only ever quote-tweet their replies … this is not a real discussion and you’re not fooling anyone). As I have written before, there was a time when sports media were the gatekeepers to athletes and management, and enjoyed considerable power as a result. Those days are long gone and it’s been interesting to watch which media personalities have been able to make the adjustment. Radio folks have always been a struggle to follow since so much of what they tweet relates to getting people to call in. Writers are generally more interesting but that is not a universal rule. TV folks are hit and miss.


Q: Which sports media feeds do you find most rewarding either from an entertainment or information standpoint?


2) Another enjoyable part of this interview for me was around the idea of columnists telling people what to think. Those are my words not his. Our friends over at Pension Plan Puppets have made an industry out of pointing out how Leafs media shape fan opinion in misleading ways. It’s easy to say that we should just ignore or laugh at bad takes but it’s not quite so simple. Most fans get their talking points from newspaper columns, and to a lesser extent prime time radio shows. These legacy media outlets still have tremendous influence over the local fanbases. If you’re hired into one of these positions then you inherit that power, and arguably the responsibility to use it for good. (Perhaps I am wrong about this.)


Q: Do legacy media influencers still have relevance in today’s sports media marketplace?



thanks for reading, commenting, and following

until next time …

mike (not really in boston)

photo credit: The Star
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