As the baseball world awaits the pending decision from Roki Sasaki, easily the most sought-after free agent left on the market, the Blue Jays seemingly still haven’t learned an important lesson.

News came down earlier this week that the Blue Jays are among the three finalists for the latest ace-level pitcher to come from Japan, which was certainly encouraging. That said, this is a team that has been a “finalist” for several of the top-tier free agents so far this offseason, only to see them come up short time and time again. There could be many reasons for that, and there certainly are depending on how many cases you’re reviewing. Whether it’s the money/term of the contracts offered, the geography, or the future of this franchise, Ross Atkins and his front office team haven’t been able to land the coveted free agents they’ve pursued, including but not limited to Juan Soto, Corbin Burnes, Max Fried, Teoscar Hernandez, and more.

And I wonder if the story would have unfolded differently if Vladimir Guerrero Jr. had already been signed to an extension.

The Blue Jays are in a precarious position right now in that they’re on the verge of losing arguably their two most valuable players to free agency, Guerrero Jr. and Bo Bichette. The duo have been the pillars that Atkins and co. have built around for the last number of years, but the window of contention is closing on this group, and it’s undoubtedly been a factor in the Blue Jays’ free-agent pursuits. The fact of the matter is that most free agents also want a chance to win in addition to a shiny new contract, and right now the Jays aren’t offering a lot of guarantees beyond this season. Even then, this was a team that had a paltry 74 wins last year, finishing in last place in the vaunted AL East.

In brief defence of the current front office, I’ll admit it’s a bit of a chicken and egg situation here, or at least it seems that way. Potential free agents likely don’t want to make a long-term commitment to Toronto without assurances that Guerrero and others will be around to help them compete for a playoff spot, and at the same time, Guerrero Jr’s camp likely wants to see a commitment to win from the Blue Jays as well before he sticks around for the next decade or more (in addition to a boatload of dough). However, I believe that there’s a remedy, and that’s to meet the demands of your franchise face, a 26-year-old who is a four-time All-Star.

Will that result in a potential overpay for the Canadian-born slugger? Almost certainly.

However, this feels like a paradigm-defining moment for the Blue Jays and one that will determine the direction of the franchise for the next 5-10 years. That matters to the current players on the roster, and even more so to future free agents. If you want to be the best, you have to compete with the best, and sometimes that means making exceptions beyond whatever your “valuation” tells you. I will give ownership some credit for pushing the payroll into the top 10 in baseball, but this is a time when they need to go even beyond that to make sure they retain one of the best homegrown hitters they’ve ever had.

As far as the Blue Jays’ pursuit of Sasaki, I can’t imagine a world where the 23-year-old phenom would choose them over the Dodgers or Padres (the other two reported finalists) without knowing that he was coming to Toronto to team up with one of the best young hitters in the game. His other two options are the reigning champion Dodgers, who continue to aggressively improve their elite roster, and the Padres, another club that is arguably in the top three in the National League right now. It was never going to be an easy sell against those two clubs, let alone the rest of the other 17 or more teams that had interest, but I honestly can’t imagine the presentation without Vladimir Guerrero Jr. being a big part of the pitch.

If Atkins and his team need any further convincing that it’s more than okay to overpay for Guerrero Jr., getting Sasaki for a league minimum (after his signing bonus) feels like the perfect reason to do so. Because Sasaki chose to come to play in North America before he turned 25, he will be arbitration eligible in three years, just as any other minor league free agent would to begin their pro career. With that in mind, the Blue Jays could pay Guerrero $30 to $40 million a year and they’re very likely to get great value between the pair, as Sasaki will make less than a million for his rookie campaign. I understand that it’s not as easy as extending Guerrero Jr. and the Jays in turn sign Sasaki because of it, but this is a unique opportunity in front of them right now.

It remains to be seen where Sasaki will ultimately choose to begin his MLB career, but I hope that the Blue Jays had more to say than “we’re confident that we can re-sign him” when Vladdy’s name came up. It’s not as if they needed another reason to extend Guerrero Jr.’s contract, but if there was ever a time for them to be borderline irresponsible with a new offer, it was yesterday.

All Toronto Blue Jays odds are brought to you by MLB betting site Betway!