On a Monday afternoon in Texas five days into the 2021 season, Vladimir Guerrero Jr. and Bo Bichette are sitting together in the Toronto Blue Jays dugout, the former with his right arm around the latter. They’re staring out to the field when the slugging first baseman gently squeezes the kinetic shortstop’s shoulder before resting his arm back on the bench. A quick conversation follows and they share an impish laugh.

The BFF moment, captured by a TV broadcast camera and shared widely by fans, resonated because of the genuine affinity and rapport between the two young stars, and there were similar scenes all summer long. Fate paired them in the Blue Jays farm system as potential organizational cornerstones and since 2017 they have essentially walked the same pro baseball path, graduating from level to level through the minor leagues up to the majors, succeeding at each step amid burdensome expectations and debuting as all-stars together last summer.

They have, over the past five years, become so synonymous with both each other and the franchise, that it is impossible to imagine the Blue Jays without them. For that reason, the most pivotal bigger-picture personnel matter facing the Blue Jays once the current lockout ends is whether to extend Guerrero and Bichette and ensure they remain together for years to come.

To a certain degree, this is a medium-term issue, as both players will be under contractual control through the 2025 campaign. That’s four more seasons, so the risk of their departure is far from imminent. At the same time, however, the longer the Blue Jays wait, the more difficult and expensive it will likely be to lock the duo up, as each year brings them closer to the open market and incentivizes the exploration of other options.

Guerrero, with the rules as they stand, would hit free agency after his age 26 season, Bichette after his age 27 campaign, meaning both will have lots of peak left to sell. Assuming they maintain something akin to their current trajectory, interest in them will be significant. The risk that creates for the Blue Jays is that they could lose two franchise pillars at the height of their careers in the same off-season. Such a possibility factored into Jose Berrios’s thinking when he signed his $131-million, seven-year extension in November, as the pitcher secured an opt-out after 2026 in case the franchise abruptly pivots to a rebuild. If the Blue Jays want to guarantee they get all the peak years from Guerrero and Bichette, this isn’t an issue to punt to spring 2025.

Already complicating matters is the inflationary pressure created by Wander Franco’s recent $182-million, 11-year extension with the Tampa Bay Rays, a deal that raised the floor substantially from the $100-million, eight-year contract Ronald Acuña Jr. signed in April 2019. A deal between Juan Soto, who is just three years from agency, and the Washington Nationals could just as dramatically alter the ceiling.

All of which means that if the Blue Jays have full conviction in both players, locking up Guerrero and Bichette is a matter worth exploring sooner rather than later.

What Would Extensions Cost?

This is obviously the most significant and contentious factor at play. The Tatis deal, agreed to after just two big-league seasons, one of which was the pandemic-shortened 2020 campaign, shifted expectations for what an emergent superstar’s early career extension should look like, especially given the Acuña contract two years earlier. And while a $340-million guarantee is nothing to scoff at, it’s worth remembering teams don’t make such financial investments unless they expect to generate surplus value. As Bichette noted when the Tatis deal was signed, “He’s probably still not going to get paid what he should have, but I think it’s good for Fernando and I think it’s good for the Padres. It’s good for baseball.”

The challenge is to find a sweet spot where both sides share risk relatively equally, the club making a significant guarantee in pursuit of long-term savings, the player locking in a substantial sum to protect against injury but surrendering the chance to truly max out.

To that end, the Tatis deal provides an interesting model, with his 14 seasons from ages 22 to 35 valued at $340 million. Guerrero will be 23 on opening day, Bichette will be 24. Like Tatis, both debuted in 2019.

Tatis hit the ground running faster than Guerrero and played more games than Bichette, prompting the Padres to jump in. When I spoke to him in November, Padres GM A.J. Preller said that they were impressed by the way Tatis “came back from his rookie season wanting to build on [it]” and the way he followed up an MVP-calibre 2020 by asking “to play winter ball because he’s been working on some things with his dad,” former big-leaguer Fernando Tatis.

“Obviously the talent part of it is very important,” Preller added. “But that hunger to be the best no matter where you stand from a contract standpoint or anything like that, we felt like he was a guy we wanted to lockup long term.”

Similar plaudits apply to the young Blue Jays duo, and while Guerrero initially lagged Tatis, he caught and even surpassed him offensively last season.