35,000 people packed BMO Field on a Friday night to watch TFC’s legends take on a Brazil Allstars side featuring one of the greatest players to ever kick a ball. The next evening, 45,000 showed up for Inter Miami and Lionel Messi. Right in the middle of all of it was our Jimmy Brennan, playing 50 minutes, scoring a penalty, and being surprised with a cake and a singing of “Happy Birthday” by an entire stadium.

From Thursday Dinner to Friday Night Kickoff

The weekend started a full day before any football was played. The Brazilian side and the TFC legends squad went out for dinner together on the Thursday night, and Jimmy said “that just got the ball rolling.” The ice was broken, the mood was set, and whatever came next was going to feel easy.

By the time Friday arrived and Jimmy walked back into a dressing room at BMO Field, it hit differently than he expected.

“You could see just in even in the dressing room, the guys were just excited just to be back in the dressing room getting changed, going back to your old routines that you used to have.”

Former pros who’d spent years doing exactly this, doing it one more time. That alone was something.

Walking out to 35,000 people was the moment Jimmy knew this was going to be a proper night. He’d told himself beforehand he’d last ten or fifteen minutes at most, keep it sensible, not push it. Then the ball started moving and “when you get out there, you start knocking the ball and it’s a good little standard.” Ten minutes became fifty. His back and his hamstrings paid the price over the next two days but by every measure, it was worth it.

Fifty Minutes With Ronaldinho: “This Guy Still Got It”

Ronaldinho is 46 years old and he still has the touch. He still has the move that sends you the wrong way. Jimmy found that out the hard way.

Standing in the center circle between runs, Jimmy had a proper conversation with Ronaldinho mid-match. He asked him how he was enjoying himself.

Ronaldinho’s answer: “I love it. I love this city, man.”

Then came the post-game invite. Jimmy, running on fumes, turned it down. “Bro, no. I’m going to the Brazen Head. I’m going for some chicken wings. I’m going home cuz I’m knackered.”

Ronaldinho loved the city. Jimmy loved his chicken wings. Both parties understood.

Before that, on the pitch, Ronaldinho still had the move. “He still has that little move that sends you the opposite way. He sent me the opposite way.” Jimmy turned around, watched him go, and had one thought: “Fuck. You know this guy still got it.”

Did Jimmy catch him? “No. You nuts, man. I didn’t catch anybody.”

What stood out to Jimmy beyond the football was the complete lack of ego. Coming in, there’s a reasonable expectation that someone carrying Ronaldinho’s career, his reputation, his profile, might hold a certain distance. Not the case.

“What a chilled, happy-go-lucky guy, man. He was awesome.” Smiling the whole game, laughing, completely in his element. Ronaldinho playing football at 46 and genuinely loving every second of it is not a surprise to anyone who watched his career. Seeing it up close, apparently, hits different.

The Birthday Penalty Nobody Saw Coming

Jimmy Brennan does not like taking penalties. He has said it on this show before and Friday night did nothing to change that. He was standing there, planning to let someone else handle it, when Giovinco walked over and closed the discussion: “Hey, it’s your birthday. You’re taking this.”

As he walked up to the spot, looking at the keeper doing his little dance. He ran through his options. Could he still get across his body and bend it into the corner? Did his legs have enough? He decided they did not.

“I don’t trust myself. I’m going to put my head down and ping it down the middle.”

The keeper guessed left. The ball went straight down the middle. After the match, Jimmy asked him what he was thinking.

“You’re a lefty. I could have swore you were going to come across your body.”

Jimmy’s response: “Yeah, I couldn’t. If I did that, I would have fell over.”

Then 35,000 people sang happy birthday to him. He had no idea it was coming.

“That caught me off guard,” and called it “a truly special moment.”

Asked to rank the three highlights of the night, playing alongside Ronaldinho, scoring the penalty, or the birthday serenade, he couldn’t do it. All of it together was the night. He also noted this was the last time his kids would watch him play.

“It’ll be the last time that I’m actually going to play a match on BMO. Like a good match like that.” So yeah, he’s going to remember it.

“Just when you think you’re retired, you end up back at home playing again. Could not have asked for a better birthday in my life.”