If you’ve watched a Raptors broadcast, you’ve been met with a booming, cheerful, extremely long HELLOOOOOOOO! That voice belongs to Jack Armstrong, who has worked alongside the Raptors for 25 years, first in radio, and then in his courtside spot as on-air analyst for TSN. He frequently brushes shoulders (and swaps coats) with celebs like Drake, and is an encyclopedia of institutional knowledge when it comes to the franchise. He’s also a wonderful singer, and recently put out an album of Christmas songs called, naturally, Hellooo and Happy Holidays, with all proceeds going to the MLSE Foundation and Special Olympics Canada.
Dime caught up with Armstrong on a recent snowy day between games and talked about his first live music performance, the Raptors current slump, reasonable expectations for Scottie Barnes, his tailgate routine as a season ticket holder for the Buffalo Bills, and much more.
Dime: You’ve always been a crooner, but how did the holiday album come about?
Ah, wow. Barry Taylor and Tim Golan from Comedy Records reached out to me, I’m gonna say four years ago, and said, “You know, we’ve heard you sing a lot on the air and we think it’d be a great idea to do this.” And I’m like, you guys are nuts. They said we want to do an album, and maybe even try to do a concert or something like that. We had just won the championship, and it it was pretty chaotic and hectic, and just literally didn’t fit at that time, and then obviously COVID took place. But every year we would chat about it. And finally, I just felt like, you know what, the the time is right. Let’s do this. Let’s have some fun with it.
The album came out in November, and then we had three days of rehearsal to get ready for the concert last Tuesday, Dec. 6. So it’s been a whirlwind. And actually, this Friday at Union Station, I’m going to be singing. I’m coming in early — I have the Raptor-Nets game at night — but prior to that they have, for commuters going through Union Station during the holidays, they have folks singing holiday tunes. So it’s just been like a whirlwind of fun, and obviously it’s for a great cause, proceeds go to the MLSE Foundation and Special Olympics Canada.
To me, Christmas is a joyous time. It’s also a difficult time for a lot of people. So it’s a nice way to bring a smile to someone’s face, and actually more importantly, be of help to somebody that needs it. And I think both organizations do a great job
And how was the concert? I’m very sorry to say I missed it.
I have a hard time being able to critique myself. I could tell you this, I was very nervous. And I’m honestly not nervous when I do public speaking, or when that red light comes on and I’m on television. There can be 1 million people on or whatever the number is that night. That doesn’t get me nervous because I’m in my realm, and I’m very comfortable.
But for this, it was different. LiveNation books you to do a concert at the Danforth Music Hall, you’re like, whoa. And you’re hanging out with musicians, and they’re like, hey, man! They’re cool and they laid back, and they have their own little pre-game ritual. So here I am, hanging out, drinking water and uptight, getting focused to do it, but once I got out there — I had a knot in my stomach the whole night, but probably a good one because it drives you to be on your game — so I think I got through it okay. The crowd was very responsive and fun. So I feel very fortunate. It worked out great, and it’ll be a night that I’ll never forget.
Did any of the other musicians give you advice when you were feeling nervous?
Well, particularly we had two young ladies that were our vocalists, and I’d only met them the day before, because when I did the album, you sing the album and then they come in at a different time and do all the backup stuff. So finally I met them the day before the concert for our last rehearsal. So we added a song really late — it was me, it wasn’t we — I wanted to salute my mom, so I sang “Danny Boy.” My parents are from Ireland. I also did another song to salute my wife with “My Way,” which is my all-time favorite song.
I sang “Danny Boy” for all of them Monday morning. I tried to sing it like I did when I was younger, but as you get older, your voice changes. So they gave me some tips on taking it down one notch. It really helped me be able to express my sincerity and the depth of my passion and love for my mom. I seek out a coaching. I like people that tell me what I need to hear. The thing I hate the most is when people tell you great job, and they don’t mean it. I want to know, I’m an open book. Tell me, please, because I want to be good at it.
On the note of coaching, you’ve been through winning and losing as an athlete and a coach, and you’ve seen the ebbs and flows of the Raptors now from your role alongside the franchise for 25 years. What is your perspective on slumps that a team goes through? Because some Toronto fans are are panicking.
It’s a game of habits, it really is. I’m not sure who the smart person was that said, excellence is a habit. Not an act. And to me, I look at the big picture of five games, 10 games, 20 games — what are the habits? What comes out? You can have a great game one night. You’re never as good as you look, you’re never as bad as you look. What is the core of who you are and what your habits are? At this point, at kind of the the third of the way through — 27 games have been played so far — you are who you are. And now you gotta look in the mirror and say, okay, how do I get better? That’s the challenge right now for them is to figure out how to create even more shots that are makeable, and make some. That’s a problem.
Also, when you’re not turning people over, can you find a way to do a better job of making it more difficult for your opponent to score when you’re not turning them over? The way they play is a fun way to play. They play really hard, they try to be opportunistic and turn you over, and get on the offensive glass, and outwork ya, and get more possessions. But when you start getting banged up, and you have Precious Achiuwa, Otto Porter, now O.G. Anunoby out of the lineup, it’s really hard because you’re asking guys in extended minutes to be able to hold up and play that way when you actually absolutely have to, so that’s a tough part. They’re just going through a dip in their performance right now. I’m a big believer in habits, and somehow, some way trying to get better at what they’re doing, and I think they can. They’re well-coached, it’s a well-run organization. They have good high character people there. The challenge is the schedule right now. The next 13 games, it’s teams that are at least .500 or better? I know a bunch of them are going to be at home. But, man oh, man, that’s tough!
But I think Raptor fans have gotten spoiled, too. What is it? Eight of the last nine years have been the playoffs? And then you win a championship in that run. So to me, I’ve said this before and I’ll say it again, if I could replicate over the next nine years the run that they’ve just had, where do I sign up? When you look around the NBA, they’ve been at the highest level in terms of standard. So they’re going through a tough time right now. There’s no doubt about it, and I think in some way Raptor fans are spoiled, and I think that’s a really good thing because there is a standard. There is an expectation.
It’s like when you’re a fan of the Yankees, or one of those iconic franchises that are pretty much in the hunt every year. It’s a different place to be, because I’ve been with the Raptors 25 years and I’ve seen a lot of years where they just weren’t very good. And I’m like, they’re 13 to 14. Okay. But man oh man, there’s been a lot of years that 13 to 14 would have been an amazing accomplishment. So as odd as this sounds it’s nice to be in this position because it shows how hard winning is. You never take it for granted. It’s a grind, it’s tough, but I also feel confident that the the people they have there, they’ll figure it out.
Yeah, I was going to say, you’ve definitely seen some lean years, to put it politely. But I’m glad you brought up expectations. When I look at the Eastern standings, 5 through 9, the records are near identical. You’ve got a team like the Kings, where their expectation for this season is to just make it to the playoffs. Something I really admired about you in terms of when you talk about expectations and being realistic is when you talk about young guys like Scottie Barnes. What is a reasonable expectation to you for someone like him in his second year in the league?
You know, it’s interesting you say that. I got really nervous in the offseason. I do a lot of appearances in the GTA, different events, and the whole thing with Kevin Durant. I love Kevin Durant’s game. Did I like how all that stuff played out in Brooklyn? No. I respect Kevin Durant the player, though. He’s going to be a first-ballot Hall of Famer. He’s got an amazing record of accomplishment and a resume.
So when I have people coming up to me and saying, I wouldn’t trade Kevin Durant for Scottie Barnes straight up, I’m going, Whoa! Hold on a minute! Slow down. I’m not advocating trading Scottie Barnes for Kevin Durant, but at the same time, I’m going, do you realize who you’re talking about? That’s Kevin Durant. And Scottie is a young player. Let’s slow down here a little bit. We did our TSN NBA season preview show, and that was one of the points I made. We’re talking about the Raptors this season, I said, people need to slow down on Scottie Barnes. He 21 years old. He’s a kid. He had a really nice rookie year, and he won Rookie of the Year, and that’s great, but here you go again, and part of being a successful professional athlete, or successful in any line of work, is the commitment to the grind and consistency and habits.
And then, when you go through those bumps, learn from them and grow and continue to get better. And they’re going to nurture him, they’re going to challenge them, they’re going to make him better, and that’s all part of it.
I saw Vince Carter Friday night in Orlando, was chatting with him — first game I ever did with the Raptors was Vince’s rookie game against Paul Pierce with the Celtics — it’s a tough journey. When I first got to the Raptors, Tracy McGrady, what, was he going into his second year? It was a struggle his first year or two in the NBA. I look at where Scottie is now compared to what Tracy was in his second year, Scottie’s ahead of that. Tracy McGrady, by the way, is in the Hall of Fame. Now they’re different players, and I’m not saying Scottie Barnes is going to be a Hall of Famer, but what I’m saying is, it takes time.
I am a big believer in the fact that it gets me nervous when the hype machine overwhelms. I think in the case of Scottie, and it’s not his fault in any way, shape, or form, but the hype machine that is sports media, social media, the NBA trying to create story lines and hyping guys up, it gets to the point where we don’t allow guys to grind and fail and learn and grow. So when they go from having a really nice rookie year, there’s a lot to learn to become great. He’s going through it now, there’s growing pains, and that’s a good thing. They’re gonna nurture him and challenge him and get him out of it, but the bottom line is too often when you have all this hype around you, and now you do fail, the failure becomes bigger than what it is. We’re making mountains out of molehills. Do I think he needs to play better? Yes, I do. Does he know that? Yes, he does. Now how do you get there?
As you said, your first game on the call was Vince’s first game. But I was curious if there are other NBA athletes that you feel something of a personal tie to, either through professional overlaps like that, or for other reasons?
There’s so many overlaps, because the fact that I’ve traveled on the Charter, particularly when you’re on the road. You’re in the hotel. You’re running to people. Ride on the bus. Yadda yadda yadda. The other night, Charles Oakley and Mo Pete were at the game. You go right over and you hug each other, and everything’s great, how’s your family? There’s so many of those guys that you know, like when I see Dell Curry, and obviously Alvin Williams was one of my old time favorites. And Corey Joseph and Jose Calderón, Matt Bonner, Delon Wright, DeMar DeRozan, Jonas Valanciunas, the list goes on.
It’s a business sometimes that attracts people that get caught up in all the glitz and glitter. I’m more about the substance, the soul of it. I always say anytime I talk to a player, or I’ve ever chatted with young people, the biggest thing, and you will agree with this because you’re in the business, the single biggest thing people want to know is when someone says, what’s Chris Bosh like? What’s Vince Carter like? What’s Pascal Siakam like? What was Kyle Lowry like? They don’t want to talk about their killer crossover, or they’re up and under move in the post. They want to know what kind of guy that person was, what kind of person they are.
That’s my way to kind of navigate a business that sometimes can be phony. I try to really focus a lot on the substance, the core, the soul, the character of the people you’re around. DeMar DeRozan is a good person. Yeah, he’s a heck of a player, I love DeMar as a player, but I love him more as a person because he’s a good man. That to me is what counts. So when I talk about Vince Carter, was he perfect? No he wasn’t. Do I think in different ways he mishandled his departure from Toronto? Yes, absolutely. On the other hand, overwhelmingly, he’s a good person. Nobody bats 1.000. People get too caught up in all the other nonsense. They spend the major on the minor, and in my opinion the minor ain’t that important.
That’s what I like about being in the NBA, because people think, that guy’s a natural athlete. No, no, they’re really dedicated. They work really hard, and they’re all very insecure, too, which is cool, because they know how fragile it is. They might walk around cocky, but they all have their own little idiosyncrasies and quirks and superstitions, which is pretty cool because they care.
I love those things the most. Because they’re humanizing, but also because they show you can have this maniacal work ethic, but then still be very human about your achievements and what they mean to you.
I’ve had a lot of Raptors fans say to me, you’re the kind of guy I’d like to have a beer with. That makes me feel good because that’s who I am. I feel I’m very approachable. I like people, I enjoy spending time with people. Someone wants to talk basketball, if they want to take a picture, I’m totally cool with it. I’m not big timing anybody, because I’m a nobody. I’m a caraway seed in the bakery of life. I’m a little spec.
And obviously in the business that we’re in now, unfortunately, is more and more of a gated community mentality. There’s that moat in front of the castle where you can’t really get to the players. The NBA, NFL, NHL, Major League Baseball, agents, teams, have created that separation. And the job I have, and what I do, is I feel like I’m an ambassador for the Raptors for the growth of the sport in Canada. To me, that’s a big deal, that Canada’s No. 2 in representation in the NBA. I enjoy hearing that. I want to make sure that some eight year old girl in Calgary or ten year old boy in Halifax that is watching the Raptors game, they had a good time watching it. So anytime someone comes up to you, you always have that choice of saying, I’m too busy, I’m too important, or make them feel really comfortable. You’re that conduit to the game.
Career-wise, you’ve been honest about putting the work in and also where opportunities can come out of the blue, like when you were fired from your coaching gig and that led to your broadcast career. I was curious how have your definitions of success changed over time for yourself, if they have?
Success for me is night in and night out, doing games. I study other analysts, like a Tony Romo — I’m a big Buffalo Bills fan. So he did the game on Sunday and I’m watching it as a fan, but I’m also watching it as an analyst. I love John McEnroe on tennis. I love Teddy Atlas on boxing. I love Charles Barkley, and all these different announcers and analysts. My standard is, my job’s to tell you why and tell you how. Frame it, give you a gem, give you a teaching point, give you food for thought — something to reflect on — and have fun. I’m not a world leader, I’m not that smart, I’m not solving any major world issues. I’m a basketball analyst.
When I started with the Raptors, a lot of people said the NBA is not going to make it. Vancouver didn’t make it, and thank god we had Vince Carter, but there were a lot of people that wanted us to fail, the old time hockey puck establishment. And there were other elements that I won’t get into, why they didn’t like the NBA.
But every single chance we can get people under our roof, under our umbrella, everybody’s welcome here. The the door is always open. So every single person that comes up to me and wants to talk basketball, I’m going to have the time to talk basketball with them because I’d rather them talking basketball than talking hockey.
On this note of longevity and expanding the game. I think of the length of NBA careers now compared to 10 or 15 years ago, how do you think that lends to or changes the shape of the game?
I think it’s great. I think the science and the efforts by the NBA and all 30 teams to really help players have that longevity and look after their wellness, it’s a great thing. And I also think it helps our game because we need more veteran players. We need more wise, mature, experienced players that can help mentor our young players. Coaching staffs are a lot larger now than they’ve ever been in my time in the NBA. There’s a reason for that. There’s so much teaching and development going on right now because the league has gotten younger.
So any way we can develop our young guys, and at the same time bridge the gap with having good veteran role models in the room as well, is a really important thing and I think very helpful, very beneficial to the league. Plus people like familiarity. That’s important, I think, to the growth of the game. I would imagine down the line after the CBA gets done, and after the new TV deal gets done, after those two things, it wouldn’t surprise me to see two expansion teams. I think that would lend itself to even more opportunity for guys to play, and more coaches and more referees, you name it.
The one thing I’m concerned about a little bit is let’s not kill the golden goose. I’m sensing an undercurrent from fans and partners about the fact that, you know, I go to Broadway to see Barbara Streisand or Denzel Washington perform, and now they’re not available that night, understudies are there, and they go, hmm. We got to find that balance and that fine line, because we really need to be respectful of our fans because they’re spending their hard earned money. The price for that ticket is pretty high, we’re a national team. People fly from all over Canada to watch the Raptors. There’s going to be greater runway for players to stay in the game, particularly if we had two more teams. Think about that, and the CBA, if we get a new one done. Fingers crossed, we do. There’s gonna be a lot more money in the pipeline. All the players are 50 percent partners with the owners. Yet let’s not kill the golden goose here.
On the note of of pipelines, I did want to talk about that, but in terms of coaching. You’ve counted Stan and Jeff van Gundy as your coaching colleagues in the past. A criticism of coaching within the NBA is that it’s a very small pool. It can sometimes feel like musical chairs with head coaching hires. Obviously, there’s only a set number of jobs and teams, but aside from expansion are there other ways you think the coaching pipeline could be further opened up for more diverse candidates?
There’s no doubt. I think the G League is a great training ground for coaches, and I really think that organizations value that more than ever, because they’re sending their scouts to those games not only coaches, but young executives, and young support staff members, young trainers and equipment people. I see with the Raptors how people paid dues with the 905, now they’re up with us, and I’m thrilled for them. You end up chatting with them about what their journey is. I think it’s very important, staff representation, there’s a value to that. It’s all about how do we help our players achieve? And a lot of times, if it’s the same type of voice or the same type of approach all the time, it gets stale. You gotta be current. You gotta be imaginative and creative.
I was reading this morning about a coach of Mississippi State, Mike Leach, that passed away, and he was kind of a counterintuitive, rebellious, not a traditionalist football coach. And yet you watch any NFL game now, or college game, and a lot of the concepts that he stressed are right in front of you now. We need to always continue to bring those voices and outlooks in.
I’m around a lot of older players that are retired now, but they’re around the game. Older coaches, older broadcasters. I’m also around younger players, younger coaches, younger broadcasters. My job is I’m always trying to see it through all the different lenses. I never want to be that guy — and it’s a daily challenge, because you’re getting beat over the head with it, “Oh, well, the good old days of this and the good old days that” — no. These are the good old days, right now. And I choose to celebrate the guys that are playing. The journey they had is different than a person in their 40s and 60s and 80s, it doesn’t mean they don’t love it as much, if not more, than those people did when they played.
I think it’s really important to celebrate their journey and their story, and be a good storyteller, and stay current with them and be excited about them. A lot of times, they’re getting slagged, “Ah, they’re making too much money!” Good for them. You wouldn’t have taken the money 30 years ago? You wouldn’t have stayed at a five-star hotel? You wouldn’t have chosen to fly on a charter plane? Oh, you did that because you wanted to do it or you did it because you had to do it, because that’s the way it was? Yeah, you paid your dues and you help grow the game and I get that, and I respect your journey. But let’s respect their journey because I’ve been in the league 25 years. I look at the guys when I first started and things were going starting to go really well in the league for players, now you hear from them going, “Ah, these young kids!” This has existed since time has existed. Probably 2,000 years ago some wise philosopher was saying, “Ah, this generation!”
My point is, to your point, we need to keep growing. Keep expanding. Keep being better. And I feel I have to be that, too.
Finally, I would be really remiss if I didn’t ask you for your Bills tailgate routine.
[laughs] Well, I’m going this Saturday. Actually, I’m the happiest guy going, because the game got flexed. They weren’t sure if it was going to be a Saturday game or a Sunday game. My routine is, so the game’s at the 8 o’clock or something, so we’re always there four and a half hours before the game. We get there, have a few beverages and stand around — I’m sure it’ll be snowing a little bit — build the fire and stand around outside and talk football and listen to music, throw a football around.
There’s a whole crew of people I tailgate with. My wife and I, we’re season ticket holders. Everyone has an assignment of what to bring. I think this week I have to bring appetizers and a few pizzas, and everyone is assigned different things. And then we’re having burgers, and hot dogs, some weeks we have chicken, other weeks we have steaks.
And then, when I’m done, I always light up a cigar and I put a drink in a in a red solo cup, and I walk over with my cigar, my red solo cup to the stadium, and then, when I get to the gate, I put the cigar out and finish my drink, and I go in to watch the game. I drive there, but I never drive home. Let’s just say that, but I have a great time. I love it. I love being a fan, cause that’s the only time I ever get to be a fan. Friday night and Sunday, is work, and I love work, work’s awesome. But Saturday night, I’m Joe Bag-o-donuts. Just cheering on my team, having a great time.
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