Vladimir Guerrero Jr deadline looms for Blue Jays

They've been here before with marquee players, extending Carlos Delgado once before letting him walk the second time, twice reaching deals with Roy Halladay, locking up Vernon Wells to what was then the longest and largest contract in team history, tying up both Jose Bautista and Edwin Encarnacion for their best years before they finished elsewhere, dispatching Josh Donaldson for whatever they could get at the very end.

Yet next Monday's deadline for a long-term agreement with Guerrero is uncharted territory for the franchise in terms of dollars and scope, as any extension will be deep into nine figures and cover the remainder of the soon-to-be-26-year-old's career.

So, this is a major inflection point for the Blue Jays, one that will define the organization for seasons to come, extension or not.

If there's a deal, Guerrero becomes a cornerstone for the next decade plus, a path that means fully leaning into his upcoming peak years.

If there isn't an agreement, the sides could still reach terms next off-season, but not without other teams having the chance to lure him away first, risking the current competitive window.

With the clock ticking, let's look at some of the dynamics at play:

The $68-million, four-year extension Delgado signed in October 2000 included salaries of $17.5 million in 2003 and $18.5 million in 2004, two seasons when franchise spending cratered amid a wider reset.

With the Blue Jays at the time running payrolls of roughly $50 million, devoting one-third to one player, no matter how elite, was unsustainable, which contributed to the decision to let him walk after '04.

These Blue Jays face no such pressure, with their 2025 payroll for Competitive Balance Tax Purposes projecting out to $273 million, beyond the second threshold of $261 million.

Even if their payroll was at $250 million, a $40 million average-annual value for Guerrero would amount to only 16 per cent, leaving plenty of room to augment around him.

And they're clearly willing to ante up for such a mega-contract, as their high-profile pursuits of free agents Shohei Ohtani and Juan Soto represented a financial Rubicon crossing for the franchise.

The discussion, then, isn't about whether the Blue Jays can afford Guerrero or how he might fit their payroll structure, it's solely about what they're willing to pay him and how much they feel he's worth.

Time and again Guerrero has said he'd like to remain in Toronto long-term and that's not something a team that's missed on several big swings - Ohtani and Soto prime among them - should take for granted.

That he's still willing to consider an extension a year away from free agency and actually suggested that he's given the Blue Jays a number that gets a deal done is significant.

Soto, for instance, seemed determined to reach the open market, rejecting a $440-million extension offer from the Washington Nationals and never engaging the Yankees last year.

Guerrero, on the other hand, doesn't appear to be leading the Blue Jays in a one-sided discussion, instead engaging during the exclusive window the team has here.

What happens if Guerrero leaves?

One of the main reasons the Blue Jays' rebuild out of the 2015-16 playoff runs went relatively quickly was that they had Guerrero and Bo Bichette waiting in the farm system.

That's not the case now, with a farm system externally ranked in the bottom third of the majors and without an obvious future cornerstone player to dream about. Allowing Guerrero (and Bichette, for that matter) to spend his developmental years in Toronto only to watch his peak with another club would be gutting.

If he were to leave as a free agent and the Blue Jays ended the season as a CBT payor, they'd be entitled only to one compensatory draft pick after the fourth round.

Given how disastrous a return that would be, the club would have to weigh trading him at the deadline if it wasn't in contention, making this some extremely high-risk asset management.

Still, even if Guerrero were to leave as a free agent, the Blue Jays could always reallocate the money for him elsewhere, but as the past couple of off-seasons have shown, there's no guarantee the players you really want will take it.

SOURCE: Sportsnet