What a Ride on the South Side!

I know what you’re thinking.  

Three straight 100-loss seasons and then, all of a sudden, out of nowhere, like magic … the White Sox just start winning???? From 60 wins to making the playoffs????? That’s basically a miracle! 

How is that even possible?

It had to be the pope, right?

HAD TO BE! ONE HUNDRED PERCENT!!!!

And look, I get it. It’s like…. 

“He loves the Sox! He put in a call to the big guy!”  

Or maybe it was The Wizard™, or sushi night in SoCal, or Miguel’s dog barks, or the dance routines in the dugout. 

Honestly, though, it wasn’t the pope or any one of those other things that led us to have such a magical year. It was….

All of those things, and more, combined.

It was us experiencing all that stuff, and becoming great friends who loved playing baseball together. And for me personally, when all those elements came together, the result was something extremely meaningful. Just nine months before we clinched our playoff berth, it wasn’t even certain that I’d have a place to play in 2026. I’d been cast off by my third MLB franchise. Designated for assignment. A man without a team.   

And that was only just the most recent setback for me in this game. Let’s just say … I’m not someone you’d envision making an All-Star team as a rookie, or playing in the MLB playoffs. I’m pretty much not even supposed to be here, if we’re being completely honest. In fact, I can give you 8 reasons why me getting to this place was a ridiculously massive longshot, just off the top of my head. 

1) I was born and raised in Winkler, Manitoba. Canada. It’s beautiful up there, but cold. By any objective measure, I should be playing hockey right now if anything. But my dad loved baseball, and the Jays, and if you stepped out the back door of our house and walked a little ways beyond a tree line, there were some baseball fields. I remember heading out to those ballfields as a little kid, going to the tiniest one, and my dad lobbing pitches to me so I could try to hit the ball all the way to the fence on a roll. We loved doing that when it was warm enough to be outside. 

2) I played competitive badminton as a kid. You know badminton, right? The light, small rackets. That white plastic birdie with the rubber red nose. I was actually even on our high school team for that. I also did hockey as a kid, of course, and soccer, in addition to baseball. And I did volleyball, too. But yeah, badminton practice was an actual thing for me when I was 14 or so. Canada, man. Gotta love it.   

3) I was huge into Beyblade growing up. You guys ever heard of Beyblade? No? Well, allow me to explain. It’s basically this spinning-top game from Japan with these insane-looking colorful plastic toy tops that kids would use to “battle” and see whose top stayed spinning the longest, or whose could knock their buddy’s top out of the battle area. Haha, as I write … I’m realizing in real time that I’m not doing a great job here. Just Google it maybe. But yeah, I loved playing Beyblade so much. When I wasn’t inside at volleyball practice or whatever, or out on the fields with my dad, I was all about that game.   

4) Summers in Winkler lasted about two months. It’d basically start snowing in September. In the winter, I’d have to go to this tiny middle school gym and throw around these totally lame squishy “indoor baseballs.” So, when I was 16, I moved in with my aunt 1,300 kilometers away in Calgary because she lived near this baseball academy in Okotoks, Alberta. The facilities there were amazing, with a huge turf indoor training space and a great weight room, but the thing is … it’s still Canada, right? I remember we’d be heading out to the field on some days and we’d literally be shoveling snow off the turf part of the infield as a team. The outfield would be completely covered, so we’d just clear these little paths for the outfielders, and the coaches would hit fly balls and grounders that basically needed to follow those paths. Otherwise the baseballs would just hit those white areas of the field and roll along gathering more and more snow. It was the most Canadian scene ever.

5) I became a position player basically by accident. When I got to that baseball academy, they initially put me as a pitcher. They had no idea I could hit. When I didn’t pitch great that fall, they decided to place me on what was the equivalent of a JV team. Then, our first game in the spring, our team scrimmaged against the varsity squad and they put me in the infield for that game. I went 4-for-4 with a homer off their best left-handed pitcher. That next morning, I was on varsity. 

6) D1 schools weren’t into me at all. I had a few D2 teams interested, Minot State was one I remember. And maybe, maaaaybe one D1 “offer,” but with no money at all. So I went the JUCO route at Chandler-Gilbert Community College down in Arizona. And guess what happened when I got down there? You know what I realized? I realized that….

7) I LOVE line dancing. Hahahah. This was 2018. My buddy asked me to go with him to this place called Scootin’ Boots in Mesa, and I decided to give it a shot. Mind you, I have no rhythm whatsoever. But it was a blast. We’d go every Friday night, and I was terrible, but it didn’t matter. I met some great friends at that place, and that first Friday night I actually met my wife for the very first time. After a while, I ponied up for a nice pair of cowboy boots. Then it was a belt with a big buckle on the front. I bought in fully, and it was so much fun! Of course, I was also hitting the tar out of the ball in Arizona at that point and did well enough to get recruited to D1 for my final year of college, but I mean whatever … you seriously should’ve seen me out there on the floor scootin’.    

8) After one season at Southern Illinois, I played for the Savannah Bananas in the summer. How’d that happen? Well, get this … THEY KNEW I LOVED LINE DANCING, so they figured I’d be a perfect fit. I’m not even joking. The Bananas manager, Tyler Gillum, had coached against me at JUCO and appreciated how I played. When he found out about the line dancing thing … I guess that kind of sealed the deal. I’d heard of them, and knew they were all about the fans, and so I said yes immediately. But at the time I definitely didn’t realize I was gonna end up wearing a kilt on the field or dancing to “Baby One More Time” by Britney Spears. Hahaha.  

Before the games, Coach Gillum would stand in front of a whiteboard and be like, “O.K., here’s the celebration we’re gonna do after our first run.” Then, “If someone hits a homer, we’re all gonna do X, Y, and Z.” And on and on. Our first base coach and choreographer, Maceo, would come in next and teach us whatever dances we’d be doing that night. It was … awesome! As much as I’m someone who takes this game very seriously, I still gotta say … that extra-fun version of baseball was wonderful. Coming to the ballpark every night with the goal of doing everything we could to make fans happy? That resonated with me. And what made it even better was that … we were actually good! It wasn’t just a bunch of clowns out there trying to LARP as ballplayers. We won the Coastal Plain League championship that year. Legit won it all. I wasn’t around for that final game, though, because by that time I had been selected in the MLB draft. 

Look, I could keep going here … like 9, 10, 11 … 20 … 50 … 100. I could tell you all about how after getting drafted in the 7th round by the Brewers, I somehow got traded not once but twice in that first 16 months. About how, that first time, I’d been planning to propose to my then-girlfriend on the field at our ballpark a week later, but then my manager pulled me aside to let me know I was dealt to the Giants and was about to be a Richmond Flying Squirrel and needed to meet that team on the road. (Note: The proposal still happened on schedule, but just in Maine, while we were playing the Portland Sea Dogs. Life, man, what can you even say?) Or how lonely I was after those trades, feeling like I didn’t have anyone on each new team to lean on, or who I could really talk to. How at times it became hard for me to see a future for myself in baseball anymore. And then how, after I actually did get called up, with the Rays, I played four games, took an 0-for-12 and badly misjudged a ball in the outfield, got roasted on Twitter, and then got DFA’d a few months later and was left thinking: What if I never make it back up and end my MLB career with literally zero hits? I could tell you about all that stuff in excruciating detail. But an article like this can only be so long, you know what I mean? This isn’t “War and Peace.” 

So instead, I’ll just keep it moving, and tell you I’m living proof that if you continue persevering and grinding and refuse to give up on your dreams, sometimes things like the 2026 Chicago White Sox run actually do happen for people.

When I got a call two days after my DFA from the Rays saying they’d found a trade partner, and that I was going to the White Sox, I mainly just felt relieved. It also helped that the Rays front office guy told me there were five other teams interested. 

It felt so good just to hear that I was still wanted, you know what I mean? I knew deep down I still believed in myself, and a few months later when the White Sox told me I’d made the major league roster out of spring training, I was starting to feel like I’d latched on with a team that did, too. 

At the same time, though, just to be completely real with you … for a good long while at the beginning of the season I was still very nervous that I might be sent down again at any moment and then … that might be it for me. I worried about that even after I notched my first MLB hit against the Brewers during the first series of the season, and after I walked off the Blue Jays in early April and then got in a groove at the plate. I’m pretty sure I had some PTSD from getting DFA’d. 

But then, before I knew it, our team was coming together like nothing I’d ever experienced before, and we were winning a bunch of games, and … I guess I was just having too much fun to worry about any of that stuff anymore. 

I know lots of people on the outside assumed we’d be terrible again in 2026, but after a few weeks everyone in our clubhouse started to sense something. It was like we all kind of looked around at each other and were like, Hold up, we’re actually nasty. Like, We’re a legitimately good baseball team!  

Plus, we were building these amazing relationships with each other, literally all becoming friends and having fun. And when you’re loose and goofy and just having fun with each other, there are times when you truly believe you can accomplish anything as a group. So yeah, no joke, from very early on … we absolutely believed that we could win the World Series. We believed that with all our hearts. 

And look, I understand why there was skepticism all year as to whether we could keep it up. But if you dig in and look at our season … we were actually very consistent. We never lost more than four games in a row at any point. We weren’t some fluke. There was nothing lucky about it. And by the time those clubhouse celebrations were taking place at the end of the season, and the champagne was flowing, it was this thing where we all felt like teenagers again. Just partying and having a blast and shouting out our home countries in unusual ways and living our very best lives. 

It probably sounds crazy to hear someone say that the White Sox getting knocked out of the playoffs was a tough pill to swallow, but man did that series loss to Cleveland hurt.

And the thing is, for the guys in that clubhouse it honestly wasn’t mainly about not getting to advance further in the playoffs. There was actually this very human side of things that kind of even eclipsed that part. For me … and I think I can speak for the other guys, too … it wasn’t like, Oh man, it sucks that we didn’t win the World Series. It was actually more like.… We don’t get to play any more games together?!?! We have to stop coming to the ballpark????  

We were just genuinely sad to not be able to hang out anymore. Not to be able to play on the South Side for Sox fans anymore. 

But on the bright side, this past season, I truly believe … it was only just a glimpse of what’s to come. I can’t wait to see what magical stuff happens next. 

And, on that note, before I get out of here, I’d like to clarify something for the record. Just to avoid any potential misunderstandings. You know how I said up top that we didn’t go on this magical run because of the pope? Sooooo, about that, for real … I definitely didn’t mean to suggest that his fandom didn’t matter. No way. 

That guy, he’s the man! We love the pope! 

And hey, should he decide to put in a good word for us going forward, or whatever, I mean, let’s just say….   

We’d be very, very grateful.

No pressure, though. All good either way. Not trying to tell the pope what to do. Whatever works.

See you in the spring,

—Tristan