TORONTO — It’s the moment Vladimir Guerrero Jr. won’t forget. It’s the one that hurts most. Lying on the ground in the Target Field dirt, Guerrero gripped second base as he waved to the dugout.

Bo Bichette froze in the batter’s box in disbelief, robbed of his opportunity to hit. Guerrero kept waving, begging for a challenge to erase the mistake. He hoped a review would give Bichette another chance — one more swing. It didn’t.

In this era of Blue Jays baseball, largely defined by the pairing of Guerrero and Bichette, a span that includes three playoff exits and six postseason losses, that 2023 pick-off against the Minnesota Twins torments Guerrero the most. He drifted off second base as Toronto’s tying run, unaware of Carlos Correa sneaking behind him. Four innings later, the Jays lost by two runs to exit the postseason.

The pick-off still lingers in Guerrero’s mind because of his teammate at the plate — the guy who’s been alongside him the whole time. The guy he so badly wants to win with.

“When I got caught at second base,” Guerrero said through interpreter Hector Lebron. “I really felt like Bo was having a good at-bat. He was going to get a base hit that at-bat. We would have tied the game.”

Bichette and Guerrero arrived in 2019 as Blue Jays franchise saviors. They represented just two pieces of a much larger puzzle, but they were undeniable top prospects tied at the hip. They dripped with pedigree and potential — the sons of former big-league stars, now the centre of Toronto’s rebuild. The franchise, Bichette said, was put on their shoulders.

October arrived as prophesied. The pair, the only players remaining from that 2019 team, have earned All-Star nods and MVP votes. They’ve achieved more playoff appearances together — four berths in seven seasons — than any Blue Jays team in the last 30 years. But postseason wins remained elusive as wild-card exits stacked up. Swept in 2020, 2022 and 2023. Punctuated with Guerrero getting picked-off.

Six postseason games. Six postseason losses.

Now they’ve pushed further than ever before. They’ve won the division and bypassed the wild-card round. They enter a Division Series with home-field advantage, starting Saturday. Guerrero struggled down the stretch and Bichette watched from the sidelines with a sprained knee. Bichette hopes to return at some point in the postseason, but the Jays may have to advance further to grant him that possibility — to earn him and Guerrero another October opportunity, together. With Bichette on the cusp of free agency, this postseason may be their last chance to replace painful memories with a pennant.

“We’ve always had huge goals together,” Bichette said. “To win as much as we can, win the World Series, if not more. So I think that it’s been a road. You kind of find a recipe that might work and we got to continue to grow that. Hopefully that’s for many more years, but it feels good to have another opportunity.”

Vladimir Guerrero Jr. is still haunted by getting picked off in 2023, when the Blue Jays fell to the Twins in the playoffs. (David Berding / Getty Images)

A flock of cameras and reporters followed Vladimir Guerrero Jr. across the turf. The swarm only grew as first pitch neared on April 26, 2019. Rowdy Tellez took batting practice on the field as the mass of bodies surrounded Guerrero. He smiled and cameras flashed. He picked up a bat, more photos. Fans, allowed in early to watch the debuting slugger with blond-tipped dreadlocks warm up, pushed to the front rows.

His Hall of Fame father observed, leaning against the dugout railing. Vladimir Guerrero Sr. wore an unnecessary name tag, a sticker on his chest. He hit 449 homers in 16 big-league seasons. He won an MVP and went to nine All-Star games. But Guerrero Sr. never won a World Series. His son would try instead.

“There were people everywhere,” Tellez said. “It was wild. We took batting practice and couldn’t even walk back to the dugout without bumping into somebody. Camera crews everywhere, people everywhere.”

It felt like the playoffs, Guerrero Jr. said. His first day in the big leagues and already a glimpse of the big stage. It’s where he wanted to be. But those 2019 Blue Jays weren’t going anywhere, two years into a tear down. Guerrero’s ninth-inning double that night was a rare bright spot amid a bad year.

The Jays sat three games below .500 when Guerrero debuted.

Bichette joined three months later when the team was 17 games under.

Yet the expectation was clear. Perhaps Tellez, Randal Grichuk, Teoscar Hernández and Cavan Biggio would be the supporting cast, but Guerrero and Bichette were the core. They were tasked with returning the October joys that José Bautista, Edwin Encarnación and Josh Donaldson brought before them. Or maybe the homegrown pair would push further — providing a new generation with the magic of 1992 and 1993 world championships.

“They did have a lot of pressure on them to perform,” Tellez said. “We were in a rebuild. We were bad in 2017, 2018, 2019. When they got here, we were excited to have them. It did bring a lot of attention to us.”

Bo Bichette and Vladimir Guerrero Jr. in 2019, the year they both debuted with the Blue Jays. (Cole Burston / Getty Images)

Their first shot in October arrived almost instantly. In 2020, the duo bounced across the Tropicana Field turf before Game 1, Guerrero spitting seeds with a bandana around his neck and Bichette’s long hair still flowing behind him. The crack of their connecting swings had seemed even louder all season, in the empty stadiums of baseball’s COVID-19 season.

Guerrero’s promised line-drive power and Bichette’s uncanny contact translated straight away. But their first taste of the playoffs quickly became a fanless first defeat.

“It was definitely not what we dreamed of,” Bichette said.

Toronto’s young pair were held to just one hit in 13 at-bats. It’s a two-game sweep that still sticks with Guerrero, he said, the first postseason pain. It sits perhaps only second to the Minnesota pick-off. But, surely, they’d have other chances.

“We had expectations,” Bichette said. “But I think we overachieved early on. So I don’t think it really got real for a couple years.”

Their second shot at the playoffs came after a one-year delay. The Blue Jays stayed alive until the season’s final day in 2021, only to watch in horror as Rafael Devers hit a homer that ended Toronto’s year. The image played on Rogers Centre’s jumbotron. Gone was Guerrero’s end-of-dugout dancing and unwavering smile. He lingered in silence, arms draped over the top rail.

“Last year was the trailer,” Guerrero said the next spring. “What you are going to see this year is the movie.”

Guerrero and Bichette made it back to the playoffs seven months after that spring proclamation. But the 2022 season ended with the Seattle Mariners dancing on Toronto’s home turf. The Mariners erased an 8-1 Toronto lead in Game 2 to complete a sweep, celebrating the comeback by locking arms around the pitcher’s mound. As the Mariners spun in a dance circle with kicking legs, Guerrero once again draped arms over the dugout railing and buried his head into his biceps. Bichette, standing in the back of the dugout, gnawed at a piece of gum as he peered out to the field.

“In a lot of ways, we were ahead of the curve,” Bichette said. “But when we started having failures, is when questions started looming in our own heads.”

Those questions only lingered after their third October, the two losses in Minnesota. Guerrero found himself alone at second base, waving to the dugout. Bichette, the bat taken out of his hand, slouched back to the bench.

The Jays scored more than two runs in just one of the six playoff games. Guerrero owns a .422 OPS and Bichette has a .638 mark in the postseason — both at least 150 points lower than their regular season norms.

Through the defeats, the team changed around Bichette and Guerrero. The Jays, Bichette said, made good and bad adjustments. They fired a manager, replacing Charlie Montoyo with John Schneider. They changed styles, prioritizing defence. They rotated through complementary veterans, traded top prospects for José Berríos and handed the franchise’s largest free-agent pitching contract to Kevin Gausman. The October success still didn’t manifest.

For Guerrero, there’s only one way to move past the quick exits.

“They’ll stay with me, always,” Guerrero said of the playoff losses. “The only way you can stop thinking about it is to go all the way and win the World Series.”

Vladimir Guerrero Jr. and Bo Bichette celebrate clinching a playoff spot 2023. They have yet to win a playoff game together. (Mark Blinch / Getty Images)

The long hair of their youth is now gone, chopped away. The banners hanging off the side of Rogers Centre featured the now-polished pair, long removed from their debuts. In his, Bichette looked off to the distance, a bat over his shoulder. Guerrero held a lone finger to his lips — his signature post-homer hush.

Those banners were recently removed, replaced with Toronto’s postseason paraphernalia. They house a simple slogan: “Want It All.”

Guerrero and Bichette have shared clubhouses for nine years, from the minors in Dunedin to the big leagues in Toronto. It has been seven since their promising arrival. These days, their lockers now reside beside each other in the corner of the clubhouse, a prime position reserved for players of their earned status.

Again, the duo played a critical role in the regular season as the Blue Jays surged to the top of the American League East in 2025. They went from 74 wins to 94 wins. Guerrero and Bichette won their first division title, earned their first bye and await their first-ever Division Series.

Standing in a drenched shirt with goggles on his head amid Toronto’s division-clinching celebration, Guerrero didn’t promise any upcoming feature films.

“The job is not finished,” he repeated three times.

The job is October success — the only thing that’s eluded the Jays since Guerrero and Bichette arrived. It’s why Bichette, who missed the season’s final 20 games with a knee sprain, hopes to return. He hasn’t yet started running. Guerrero may have to go it alone in the Division Series to earn Bichette a shot in a future round. He’s doing everything he can to come back, the shortstop said. That job is why Guerrero, covered in champagne and beer, held his focus on the future.

Bichette hopes he’ll have many more opportunities to achieve October success alongside Guerrero. In reality, this could be their fourth and final shot. Though Guerrero signed a 14-year deal with the Blue Jays in April, Bichette’s future with the franchise remains up in the air.

Together, Guerrero and Bichette shouldered the Blue Jays through a rebuild. They brought the team back to the postseason three times and fell short each time. But now, they won a division. They hold a bye. The team around them is as good as it’s ever been. It’s a chance, perhaps their best one yet, to do the one thing they’ve never done — achieve the October success they yearn for.

“It’s going to be special,” Guerrero said. “It’s going to be special. We’ve been playing together since 2017. There have been a lot of ups and downs, a lot of happiness, a lot of crying, but it would be very special to win a World Series with Bo.”

(Top illustration: Dan Goldfarb / The Athletic; Mark Blinch, Scott Taetsch / Getty Images)