Intro
I was suggested to reach out to Jack Stern way by Kyle Lesniewski, who I interviewed in the post before this one. They crossed paths originally when Kyle was at Brew Crew Ball as the managing editor and brought Jack on. They both have similar interests as far as the Brewers, analytics and coaching. He is currently the Milwaukee Brewers beat writer for Brewer Fanatic as well as an assistant coach with his alma mater’s baseball team, the Western Lutheran College Warriors near Milwaukee.
We talked about how he reached his goal of covering a Major League Baseball team through lots of study, practice and long hours.
You can read his work at Brewer Fanatic and follow his Twitter account here: @ByJackStern
Getting Into Covering Baseball
When you got into covering and writing baseball, was it the analysis and stat side that got you going?
Once I kind of realized that I was just not gonna be able to make it as a player, when that reality kind of hits you, you pivot to, ‘OK, well, I still really love this game more than anything. So how do you find ways to keep staying involved.?’ I always knew at that point I really liked sharing my takes, my thoughts, and my analysis on baseball. And from there, it was kind of, ‘OK, if I want to do this as more of a career, you got to get good at it and you got to find a way to better back up what you're saying,’ I guess is a good way to put it.
So that's where you get into some of the statistical side of it, the analytics side of it, because that does give you a little bit of a niche that other people don't have. And this is at a point in time when all this stuff was barely starting to become mainstream for baseball fans. I think if you look at it now, a lot of fans are at least familiar with some of this stuff, but you were in that era of a more widespread data revolution across people who were either covering baseball, following baseball, whatever it may be. I started digging into it a little more and learning more about it, applying it more and it just kind of grew from there. I got really well versed in this stuff.
Not only that, but also learning how to explain it to people in a way that doesn't sound super technical or super jargony or super nerdy. That's the whole point of it, too. If you're going to make use of this stuff, and if you're going to illustrate for people why it's valuable and what it can tell you, you've got to be able to put it into layman's terms and you got to be able to explain what it actually tells you about what's happening on the field. Because at the end of the day, that's what it always comes back to.
You’re enthralled by the action that's happening on the field. And then if there is this other stuff out there, this information, this data, these analytics, these different ways to look at and explain things, if you're able to use that to supplement that and to enhance that excitement for what's happening on the field, I think that's a really great thing. So that's my mindset toward it. That's the approach that I took as I was getting into this.
Did you go to school for journalism?
I was a communications major (at Wisconsin Lutheran College in Wauwatosa). It's not a full on journalism degree, but within the communication major, there are a couple of different areas of emphasis, so there was a journalism and media emphasis. That's the area of study that I took. At that point, I already knew this is what I wanted to do, so I figured that was just the best way to go to stay on that track and to get to where I wanted to be.
Was it harder to learn the details of baseball analytics or harder to develop your method for writing about it and relating it to readers and fans? It’s one thing to write a very technical style that loses 95% of the audience, it’s another to put it on paper in a way people enjoy and can digest.
That's the whole name of the game really. If you can't explain it to people and help them understand it, no matter what the information is, it's completely useless. Good writing needs to be clear, it needs to be concise. People need to be able to pick up whatever you wrote and actually get something out of it. It needs to be something that they can understand. And that becomes even more important when you're adding in something that can be a little bit more advanced at times.
It really just comes with experience. Learning these things for yourself, first and foremost. In kind of a roundabout way, it does help a little bit in that, to understand this for yourself, you have to simplify it for yourself first so that you can get a grasp on it. I do think one thing that helped me with this is, sometimes you have people who try to explain this stuff, and you can tell that they're coming from more of like the stats or the math or the data background. I've always been terrible at math. I was always coming at it first from the baseball angle, and I'm just trying to understand all this stuff in terms of baseball, in terms of what it means for what's going on the field. As I'm learning this stuff for myself, I have to maybe talk to someone else who's able to explain it better, or just keep reading about stuff and keep thinking about it. You have to get to a point where you've simplified it for yourself first so that you can understand it, and if you're able to do that, I think that makes it easy to turn around and do that when you're trying to explain it to your audience.
I also see that you're all set up for video and podcasting and radio, too. Have you used that to get a step up in your career and more exposure?
Within the media landscape in general, it's really valuable to be able to do a lot of different things, to be able to communicate a message in a lot of different ways. Whether that's writing something, or video, podcast, radio, whatever it may be. I've kind of done it all at this point. I've done writing. I do radio hits. I've been on news stations to talk about baseball. I think that just helps you reach as many different audiences as possible. I think in a way, too, it helps with what we talked about before, just being able to communicate stuff clearly.
It's nice to not only be writing something down and communicating baseball concepts that way. I think it's helpful, too, just to have the opportunity to verbalize it and to talk about this stuff; whether it's audio, video, whatever it may be. I think having multiple channels helps you in a lot of different ways. It helps you reach more people. I think it helps you become a better communicator, too, just because you are in a position where you have to adapt a little bit based on whatever medium you're using. So if you have the ability to write and speak and talk about whatever it is you're covering, I think that's really helpful.
How long have you been doing this?
So I started publishing at Brew Crew Ball in 2018.
So that’s not a long time, but in the recent media world, that is a long time ago. Other people I've talked to that cover baseball for blogs and digital media, they've said that they’ve been granted a lot more access the last two or three years than they ever had before. Have you noticed that? And has that helped you, A: reach more people, and B: learn more and be able to gather more information by getting more access from the team?
It's definitely a lot different than it used to be. I'm very, very lucky that I'm around during this era of sports media. If you go back just a few years, the kind of opportunities that I've had would not have been available to me. If you go back a few years, a Major League Baseball team, especially the Brewers, would not have been giving a credential to someone who writes for a blog.
The fact that there is more emphasis now on more public, open-ended platforms like Twitter, it makes it so much easier to get your voice out there. That in recent years has become an increasingly prominent source of where people get their information from. Nobody's gatekeeping you when you're tweeting something out. You can say whatever you want. You can put it out there. It's there for people to find. You don't need to go through anyone to get that information up or to get your thoughts up. And the fact that I was able to start doing that, that's really how I built an audience. It's where most of my professional opportunities came from. I was able to write stuff, post it online, tweet stuff.
So for as much noise as there can be on social media sites, the cream rises to the top a little bit. If you have people who are consistently putting out quality content, people are going to see that now and it can lead to really cool opportunities. That's definitely what happened for me, so I'm very lucky that I'm around during this era. The landscape has definitely changed a lot with how people are consuming their media, consuming their information, consuming sports and it's been extremely beneficial for a lot of people, not just myself. The amount of exposure you can get now and the amount of access you can get as a result of that I think has definitely exploded from where it was even just a few years ago.
The wild thing is that when you realize Jack has had his work published online for years and he’s only 22. Meaning he has been at this since he hung up the cleats as a sophomore. When I was a sophomore in high school, I was more concerned with getting a full page written down to turn into my English teacher. He was busy putting together a body of work that got him to where he is right now, covering his hometown baseball team at an age where he’s only older than one player on the active roster for the Brewers (super-prospect Jackson Chourio).
Progressing his Media Career
You're credentialed now. Was that recently? Did you ever see that happening when you first started?
So this is the first year that I've been credentialed. It was always my end goal; the stuff that I'm doing right now is what I wanted to do for a career: be at the stadium as a credentialed media member covering a Major League Baseball team. It's especially cool because it's the team that I grew up cheering for my whole life. But I never would have guessed that it would have happened this quickly.
How has having the credential as a member of modern media, and not legacy media, changed your approach to covering the team or has it changed your approach?
I think it has changed a little bit. I think you get the benefit of having context for things when you're around the team. Seeing these guys every day, I think that it makes you more knowledgeable. Because whenever you're trying to write from the outside, there's always some level of speculation. No matter how much you try to base all of your analysis and all of your content on factual information or logical reasoning, or trying to be as nuanced and level headed as you can, you can't quite fully capture that until you actually get the opportunity to be around players, be around coaches, be around a big league team, be around a big league clubhouse.
It just gives you more context and you get to see more things and it just makes you more informed. That's always a good thing when you're trying to cover a team and put out the best kind of reporting or the best kind of analysis that you can. Now if you ever have any questions about something that you might be trying to write a story on, if you're able to go up and talk to a guy and actually ask him questions and get the answers to what you're diving into, again, it just makes you more informed and it means that you can now really feel confident that you're writing on things that are completely, factually accurate because you get it straight from the horse's mouth.
How do you keep the brain churning with stories and content, especially these days where if you're not posting content, you disappear from people's minds? Do you choose what to write about?
My editors give me the flexibility to write about anything that I want to write about, within reason. Sometimes they might give me some suggestions like, ‘hey, here's a story idea, can you try pursuing this and see where it leads you?’ So sometimes I'll do that. But I think in general, just as far as maintaining content and sticking to a soft posting schedule, for me, it's always been, if I'm immersed in the game, ideas will just pop up organically. It does get a little bit tougher sometimes when the Brewers are on the road because I usually don't travel to road games. When you're removed from it a little bit, then it can be tougher to think of some ideas, but if you're in the middle of the home stand, you're at the ballpark every day, you're seeing these guys every day, you're covering these games every day, paying really close attention to all kinds of stuff, ideas usually tend to pop up pretty organically.
There might be a couple of ebbs within the year where you're having a hard time thinking of something, but for me it's always been as long as you're immersed, there are so many little moving parts that go on in this game. It's a game of adjustments. It's a game that can be a chess match between the batter and the hitter. There's just so many little things that happen in this game that I think if you're really paying attention and you're really being thoughtful about it, there's never really a dramatic shortage of things that you can cover because there's always so many little things going on.
Are you excited to cover the postseason?
Absolutely. I'm very excited for that opportunity.
Where do you see yourself in five years? So you got started 5 or 6 years ago and this is kind of all you've ever known. Do you have any goals or things you hope to accomplish in the next 5-6 years?
Mmhmm.
Besides getting a World Series in Milwaukee, yeah.
Right, yeah. I think the next step for me is just working my way up to a more established major publication. Right now, I'm still very much in the new media scene. And there are a lot of things I like about that, like what we've talked about so far. But there are still certain perks to working your way up past that and getting into more of the legacy media, so to speak.
Is there anything you do to take your mind off of baseball? You're basically 24/7/365 with it, and even I can't handle that much baseball.
When I'm not covering baseball, I try to unplug as best as I can. I like to spend a lot of time off the grid. I like to go out, I like to hunt, I like to fish, just spend a lot of time outside in nature, just unplug from all of this stuff. Or sometimes it might just be sitting by myself one night, pouring a bottle of whiskey and listening to some music.
Just different ways to kind of disconnect and unwind. I think that's a very important part of staying healthy mentally. You can't keep yourself immersed in anything 24/7, especially baseball, because a baseball season can get so crazy. It's 162 games plus the playoffs. There's stuff going on almost every day. It can get a little frantic sometimes, so just being able to have that balance where you can still unplug a little bit, have something that you like to do that doesn't require you to be connected or wired in or super immersed. Being able to get off the grid, spend time with people who are important in your life: family, loved ones, friends. I think those are all things that are very important. So that's what I try to focus on when I'm not doing baseball stuff. You never feel like you have a perfect balance of it, but I feel like I do the best I can to try to keep that balance in a healthy spot.
Do you find that harder to do since your job is so online? You're now a person that people get their news from. Do you find that hard to resist that pull to get back in there and make sure you didn't miss anything.
I actually think it's gotten a little bit easier these last couple of years. I think this year has actually been the easiest for me. When I was in college, I'm still working on all of this stuff in the background. Like, this is what my free time would be dedicated toward when I wasn't worried about my studies or different things like that. Now that I'm fortunate enough to call this my career, I have more structure to it. I have more clearly defined responsibilities for my job. The expectation is that I go in-depth when the Brewers are at home, because those are the games that I cover on site. I have access for those games. I'm credentialed at American Family Field, so that's really when I go all in on this stuff.
When they're on the road now, those can be my breather days. You're not running around talking to players, talking to coaches, sending out live updates during a game. You're not on site anywhere. So I think it actually has gotten a little bit easier now to balance that stuff and take a step back. Obviously, if something really major happens, even when they're on the road, I might still be called on to write something up quick or put out a reaction to it or some kind of analysis. But by and large, I think that now being able to call this my career has been a really huge blessing for me because now it means that when I'm not doing “work”, so to speak, I have a hard time even calling it work just because I like doing it so much, but when I'm not working, now my free time I can set aside for some of those hobbies that are probably a little bit healthier for me than constantly being plugged in and being online.
So I think that it's actually gotten to a spot for me now where it's a little bit better in the exact balance of how much time I might dedicate to baseball work versus some of my other hobbies. I don't think that's ever going to be the same. And like I said, I talked about wanting to get more professional opportunities, work my way up. If I get to a more established place, I'm going to have a heftier set of responsibilities, even beyond what I put in now. But still I think as long as it's my career and it's my main job, that means that there are going to be times when I'm not working and then those are the times where you can kind of take a little bit of a step back.
I’m happy to see that baseball media is gaining more access. Because better access gets you better content. Better content is better for the sport, and generates revenue. It felt like for a decade or two, the online sports media market was almost lawless. You had these pop up blogs and companies that were content farming to whoever they could get to do it for free or practically free. Now you’re starting to see more quality and the league and industry is taking notice and granting the access that they’ve earned. Much like Sox Machine from an earlier interview with their hiring of a White Sox beat writer (that poor soul), adding Jack on the Brewers beat only enhances the coverage surrounding the team.
As Jack mentioned, while today everyone can get their thoughts online for the world to see, the cream does rise to the top. So by being consistent, thorough, fair and accurate, you gain the trust that you formerly had to earn working in old-school media. And as writers like Jack, who strive to improve their writing, coverage and knowledge everyday, get these opportunities, it will only lead to more openings and avenues for future journalists. Not only that, but by reaching a point where people can cover sports and still make a living, you don’t get guys who work 12-hour office jobs and then stay up all night cranking out posts and burning themselves out. You can enjoy some whiskey, go take a hike or a day off, and come back the next day ready to tackle the coverage with a clear head.
Baseball Fan
How did you get hooked on baseball to start?
It really started, probably around age 10, growing up, playing baseball, always being around the game. It's hard to explain. There's just something about it. You fall in love with it pretty early on. You realize how much fun you're having when you're out there. It's kind of hard to put into words a little bit, but there's some kind of quality about it that I think I always gravitated toward. The strategy side of it, on top of being on the field... they call it A thinking man's game, too. And I think that was always something that I always gravitated towards just because I like all the nitty gritty stuff that's part of the sport.
How long did you play?
I was never a good athlete growing up. So I played up until I got into high school. Once I got into high school, and everybody started getting bigger and stronger and better than me, and I was not getting bigger and better and stronger like they all were, I didn't make my baseball team my freshman year high school. I was going to try out again my sophomore year. At that point, I could tell, despite trying to put in the work, I wasn't getting any better. I played up until high school and then after that started pivoting to the stuff that I do now.
I’ve realized that baseball is the one sport where everyone hits a point where it's too hard; whether it’s T-ball or they're 45 years old, it gets too hard for everybody at some point. So you’re also a lifelong Brewers fan?
Yeah, grew up a Brewers fan. The first years that I started following a little more closely, 2011 is like the first year that I can remember really paying a lot of attention to it, so you're kind of on the tail end of Prince Fielder’s last year, Rickie Weeks, Corey Hart, a lot of those guys. You had (Ryan) Braun obviously at the center of that core, too. That was the first group that I can remember really watching closely. (note: Prince Fielder’s last season in Milwaukee was in 2011. After a 38-homer campaign he signed with the Tigers for 9 years and $214million).
Talking about the Brewers now. Did you have any expectations going into this season? This is a surprise for everybody that they're one of the best teams in baseball.
I think everybody, I shouldn't speak for everybody, most people thought that the Brewers were going to take a step back. Even the more optimistic folks, I think it was just a matter of how big of a step back did you think it was going to be. A lot of the national pundits thought that the Brewers were going to be headed for a tear down rebuild. That's not really how the Brewers operate. In fact, their entire vision has been to avoid a rebuild. That's why they trade some of these guys on expiring contracts, so that instead of losing them for nothing, they're able to reload with some guys who are usually just about big league ready, like in the Corbin Burnes trade. They got Joey Ortiz and DL Hall back. Those are two guys who have contributed in the big leagues this year already. Joey Ortiz has been their starting third baseman the entire year and he's having a really nice rookie season.
So they make those kinds of moves specifically to avoid a rebuild, and they're very clear about that. But I think for people who don't cover the team as closely, it's easy to miss that. So I think everybody in Milwaukee figured they were still going to compete. I think I was one of the more optimistic people covering the team. Even I said, especially after (closer Devin) Williams got hurt, I think 86 or 87 wins was the number that I threw out, and they've even exceeded that. So going into the year, I knew they were going to be competitive. I expected that, because if you followed this team long enough, you know that that's the plan every year. I was not expecting one of the best teams in the National League though, so they've surprised me a little bit on that front. I figured they were going to be better than a lot of people, especially nationally, projected they were going to be. I did not have them making out this good. So they've done a really nice job.
Yeah, they've got the best run differential by far.
Yeah.
Eighteen runs above the Yankees. And about 1/3 of the payroll.
Yeah.
I asked Kyle about that, too. Because being a fan of a small market team that operates like the Rays, or the A's, when the A's were functional, and he mentioned that from a content creation standpoint, he almost had infinite stuff to write about, because you're always writing about people nobody has heard about. Whereas if you cover the Yankees, everyone's writing about Juan Soto and Aaron Judge. I imagine that having a team like the Brewers, who have been successful and had a high turnover rate, has helped that part of your career at least.
It's a pretty good situation to be in from an analyst standpoint and a content creator standpoint because, if you look at these Brewers teams, they've been competitive every single year starting with 2017. The roster has looked pretty different almost every single year. The only year where they returned most of their team was from the 2021 season going into 2022. Other than that, there's been a lot of turnover every single year. You've had a couple of mainstays during that time. Christian Yelich has been here every year since 2018. Freddy Peralta has been here every year since 2018. But other than that, there's been a lot of turnover in that time, and they just keep finding ways to keep cycling players through. It is fun from my vantage point, because every time that they scoop a guy up who a lot of people don't know about, it becomes an opportunity to flex your analyst muscles a little bit and think to yourself, OK, what did they see in this guy? And again, it's like a puzzle. You go in, you start looking at all the data that's publicly available on this pitcher, and you start to pinpoint like, OK, this is something that he changed last year or here's something that they can work with and maybe tweak and help him break out a little bit.
Baseball is a thinking man's game, and I think that when you're a small market team, from a baseball operations standpoint, there's even more emphasis placed on that thinking. You have to be really smart. You have to be a little bit more frugal with some of your moves, you have to be a little bit more efficient with some of your moves. You can't afford to dump massive amounts of money into single players. When you're in the kind of market that the Brewers are in, you have to do it a little bit differently.
I think part of the reason why the Brewers have become one of the smarter front offices in baseball, and why they've had so much success developing underrated or under-the-radar names, is because they have to do it this way. They were kind of forced to figure that out to survive and to stay competitive. It just it opens up a lot of opportunities for being able to explore some of these stories, being able to break down some of these players. Every year, there's a new guy who kind of comes in under the radar. A lot of times there are multiple opportunities for content there. When the Brewers first pick that guy up, that's when you can do some independent research, look at all the stuff that I talked about and then write a story up with your own analysis. And now when you have the access like I have this year, if a few months pass by and that guy is having success, you can go and talk to that guy. You can talk to some members of the coaching staff and you can get a little bit of confirmation, like, yeah, this was something that we picked up on or here's something that we worked on that got that guy to this point. You can follow that story as it's progressing and I think it's really cool.
It's also just really cool from an interpersonal standpoint to see these guys who have had to grind to get to where they are now and, after putting in a lot of work over the years, they've ended up in an organization that has been a great fit for them and now they're having success on the field. It's also just nice to see those guys get some of the results as a payoff that they've really earned from all the work that they put in. You look at guys like Colin Rea, Tobias Myers, Jared Koenig, guys who have all pitched really big innings for the Brewers this year, these are guys who were always under-the-radar names. Myers used to be a bigger prospect, but his prospect status flamed out because he struggled so badly in the minor leagues. These are guys who not a lot of people would really pay attention to, but they're all hard workers. They've really had to grind to get to where they are now. They got here because they love the game. They kept going. They kept putting in the work.
And after years of that process, they're now pitching for a first place team, getting big innings for a first place team that has the best run differential in baseball. It's just a really cool story to cover. Simply because from a process-based standpoint, when you look at some of the more technical stuff, I think that's cool. But it's also cool personally and interpersonally to see these guys having success; you're happy for them.
Is there anything about baseball you wanted to bring up that I might have forgotten to ask?
I can keep it kind of cliche. It's fun. Baseball's fun. Not everybody follows it in the same way. Not everybody analyzes baseball in the same way. You might have some people who are into the new school stuff like I am. You might have some people who don't really care for some of that stuff, maybe keep a little bit more of an old school mindset. I do think that's a beautiful thing. Baseball can bring a lot of people together. And I think that no matter how you're following it or covering it, no matter what your role is, whether you're a fan, a player or a coach, an analyst, writer, front office executive. It's fun. Just have fun. Baseball is fun. It's a fun game to watch. It's a fun game to breakdown. It's a fun game to consume. Baseball's awesome. I love baseball. Have a good time with it.
You weren't born in the 2000s, were you?
2002.
My first 2000s interview.
That's quite a distinction. I don't know how to feel about that.
I’ll have to do more research on the Brewers roster. But that was wild that going back to 2018, only 3 players are still on the team. And even just from 2021, there’s 7. I’m not sure what the league average is, but to be able to be competitive with that kind of turnover is impressive. It also means a lot of people will be searching for analysis of these lesser known players and more articles for Jack to print.
After my interviews with Kyle and Jack, I now feel bad celebrating the 2023 Wild Card round the Diamondbacks took last season. So this season, I’ve gotta root for Colin Rea and the Brew Crew.