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. And there won’t be an escape hatch for the team like there was with Dave Stieb’s “lifetime” contract signed in 1985, which ran 11 years at roughly $16.6 million with deferred payments and incentives worth up to $10 million more, although only three years and $12.6 million was guaranteed.
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.
“You all know our desire to have him here for a long time,” GM Ross Atkins, in limited comments about Guerrero during Max Scherzer’s introductory Zoom call, said last week. “We’ll continue to work towards that.”
With the clock ticking, let’s look at some of the dynamics at play:
The Blue Jays can afford this — 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.
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.
Guerrero wants to stay — 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.
Elite young free agents get paid — Despite never having thrown a pitch in the major leagues, Yoshinobu Yamamoto signed a $325-million, 12-year deal in December 2023, with the Dodgers paying an additional $50 million posting fee to his NPB club Orix. For context, that far exceeds the career earnings of future Hall of Famer Clayton Kershaw, which are just under $300 million thus far.
How does that make sense, you ask?
Yamamoto was heading into his age 25 season when he signed and with his combination of elite talent and youth, a frenzy broke out because players that young and that good rarely become available. As a result, several big-market clubs pursued him, driving the price up, the same dynamic that helped Soto get $765 million.
Guerrero hits the open market at 26 selling his age-27 season and beyond, which is right in that similar sweet spot. Only exceptional players reach free agency so young. Aaron Judge, for instance, didn’t reach the majors until 24 and only became an all-star for the first time at 25, the same age Guerrero earned his fourth selection.
In theory, his best years are coming up.
Will Guerrero get the same frenzy as Soto or Yamamoto?
We’ll see, but when you look at future free-agent classes, it might not be until Gunnar Henderson finishes the 2028 season at 27 before another MVP-calibre player hits the open market so young. Players of this ilk often get locked up early. Guerrero may be an opportunity teams don’t want to pass up.
First basemen haven’t been getting paid — The biggest contract ever for a first baseman — not including players who signed at one position and moved later — is Miguel Cabrera’s $248 million extension with the Tigers signed in 2014 covering 2016-23. Given that he had $44 million and two years left on his previous contract, the total package became $292 million over 10 years.
Whether the position’s reduced defensive value relative to other spots on the diamond justifies a penalty is up for debate, but Guerrero should crush Cabrera’s total.
Soto isn’t a strong defender and may very well be a DH in the next few years and that didn’t hamper interest in him. Guerrero may not be as accomplished an offensive player as Soto, but through their first five-plus seasons, their numbers are closer than you might think.
Even during Guerrero’s down production seasons of 2022 and ’23, his underlying hitting metrics remained elite, making his combination of youth, elite exit velocity and abilities to make hard contact while hitting for both average and power highly coveted, no matter where he is in the field.
Back in 2000, that $68-million deal the Blue Jays gave Delgado made him not only the highest-paid first baseman in the majors but also gave him the sport’s top AAV. A quarter-century later, Guerrero is positioned to reshape the first base market, whether with the Blue Jays or another club.
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.
