rewrite this title Vladimir Guerrero Jr. Gets 500 Million Reasons to Change His Mind

Vladimir Guerrero Jr. broke off contract talks with the Blue Jays on February 17. It didn’t seem like there was any animus between the two sides at the time, but the four-time All-Star didn’t want to distract himself during his walk year by negotiating all season long. The deadline was arbitrary, but nonetheless immovable. The Blue Jays tested Guerrero’s resolve with a renewed offer on Opening Day, but he held firm.

Then he changed his mind. I try to avoid the impulse to tell baseball players what to do with their careers, but I’ll say this: $500 million is a really, really good reason to abandon one’s previous position.

Guerrero’s $500 million contract extension with the Blue Jays starts next year, runs for 14 years, and contains a full no-trade clause but no opt-outs. The intention, then, is to keep Guerrero in Toronto for the rest of his career.

By the termination of the contract in 2039, Guerrero will be 40 years old, and almost certainly will have demolished every franchise record. It’s a fairly young team, but Toronto has also had a habit of hanging onto franchise icons for only part of their careers; just 12 players have appeared in 10 or more seasons for the Blue Jays. Dave Stieb holds the record for most seasons with the Jays with 15; Guerrero will have 21 if he plays out his contract.

With his extension still a full season away, Guerrero is the active Blue Jays leader in games played (829), hits (915), plate appearances (3,585), and home runs (160). He’s more than halfway to the late Tony Fernandez’s club record in the first two categories (1,450 games, 1,583 hits), and Carlos Delgado’s record (6,018 PA) in the third. As for home runs, Vladito probably will be halfway to the club record (336, also held by Delgado) by the end of the month.

The Blue Jays currently have one retired number: 32, in honor of Roy Halladay. Guerrero’s contract is a down payment (and a huge one, if we follow the metaphor) on putting no. 27 up on the wall someday as well.

When it looked like Vladito was going to take his free agency case to market, I wrote about the paradox that made his value so difficult to pin down. On one hand, he’s 26 — and just turned 26 — and a middle-of-the-order bat with MVP upside. On the other, despite his durability (Guerrero’s missed just 12 games in the past five seasons), his relative lack of athleticism makes it difficult to project the next decade of his career with much confidence. Most mid-20s free agents who sign these super-long contracts — Alex Rodriguez, Bryce Harper, Manny Machado, Corey Seager — did so with an eventual slide down the defensive spectrum priced into the equation.

For example: Harper was a right fielder when he signed his 13-year contract with the Phillies in 2019. In fact, he’d made 59 starts in center field for the Nationals in his walk year. Injuries forced Harper into a full-time DH role for about a year’s worth of games across 2022 and 2023. Now, at 32 and halfway through the contract, Harper’s a full-time first baseman and has developed into a pretty good defender there.

Guerrero was a full-time first baseman and DH, and not a very good defender at the cold corner, at 21. I suspect that by the time this contract is over, Vladito might still own a first baseman’s mitt, but he won’t know where it is on any given day at the ballpark.

In short, I’ll repeat what I wrote two months ago: Is Guerrero more Juan Soto or more Pete Alonso?

The Jays are betting the former. This $500 million contract contains no deferred money — apparently a major sticking point in previous rounds of negotiation — and is therefore the second-richest contract in baseball history in terms of real-world value.

This is a ludicrous amount of money. It dwarfs the petty low-nine-figure deal Jackson Merrill signed last week, among the Great Extension Craze of 2025.

Having already laid out the pros and cons of Guerrero as a free agent, and having already read Dan Szymborski’s ZiPS-informed take on Guerrero’s value, which ran a week later, I don’t want to spend too much time re-surveying a landscape that hasn’t changed in a week and a half of games.

Instead, I want to tie Guerrero’s extension back to the ones Merrill and Kristian Campbell signed last week. When a top-10 global prospect reaches the majors at an age when most people are playing Beerio Kart until 4 AM, the standard procedure is for the team to lock him up to a long-term contract that eats up a couple free agent years.

Why didn’t Vladito sign a contract like that? Well, if Vladimir Guerrero Sr. had been a cab driver or a fisherman, his son probably would’ve been bowled over by the idea of making $60 million or $135 million in the first half of his career. Instead, Guerrero père was himself a Hall of Fame ballplayer, who made $125 million in salary — and this is in early 2000s money — over a 16-year big league career. The Guerreros wouldn’t be awed by the financial largesse that made Merrill a Padre for the next decade and want to stay in San Diego for life.

Moreover, Guerrero fils cashed in big, and early, by playing the market straight. At 16, he signed with the Blue Jays for $3.9 million, the fourth-largest bonus in his class. He was in the majors within four years, and by his age-23 season he was into arbitration, where he made $70.8 million over his final four years of team control.

In short, this is a guy who can afford to stay at the roulette table for another spin, rather than cashing out and going home early. Most equivalently talented players — few though they may be, there are enough to infer a general trend — are content to settle for generational financial comfort, rather than sticking it out to chase every last dollar.

One side effect of the extension trend is the dilution of the free agent pool. Ideally, if the Blue Jays had $500 million to spend on a superstar, and they had concerns about Guerrero’s athleticism or his groundball rate or his consistency, they could search the free market for another hitter who could post a 160 wRC+ or better.

The thing is: Where are you going to find one? Looking at the other standout hitters from the 2019 rookie class, Yordan Alvarez and Fernando Tatis Jr. both signed big pre-arbitration extensions. So did Ronald Acuña Jr., who might otherwise be hitting the market around now.

Actually, let’s just lay it all out there. Here are, let’s say, most of the active position players and starting pitchers who had between five and six years of service time on Opening Day. I drew an arbitrary line for quality somewhere between Lane Thomas and Harrison Bader. You’re welcome to quibble, but I hope we can all agree that if the Jays had let Guerrero walk and offered, like, Brendan Rodgers as a substitute, there would’ve been civil unrest throughout Ontario.

We’ve got 24 players here who would be first-time free agents after this season based on service time alone. Guerrero is the youngest player in this group, but he’s not the best. If these 24 players were in a draft for a potential franchise player, there’s almost no chance Guerrero would go in the top three, and a non-zero chance he falls out of the top 10.

Guerrero is ninth on this list in career WAR; I think this undersells the peak value of his bat quite a bit (he was no. 1 in WAR last year), but let’s go with that as a baseline. Of the eight players ahead of Guerrero in career WAR, six are under team control through at least 2028. In other words: The cream of the 2026 free agency class has already been skimmed off the top.

Let’s set aside all that sentimental number-retiring stuff for a second, where the kid who was born in Montreal and signed with the Jays at 16 ends up spending his whole career in Toronto and rewriting the record book. That’s a great story, and a better reason to sign a player than a lot of people recognize, but it doesn’t show up in the standings.

Instead, let’s focus on the proximate on-field issue: Toronto needs somebody who can anchor the lineup for the next five years and has money to spend to acquire one. Let’s say the Blue Jays decided Guerrero was not, in the words of the poet, that somebody. In each of the past three offseasons, there was a generational irreplaceable hitter available in free agency: Aaron Judge, then Shohei Ohtani, then Soto.

There isn’t really a guy like that this year. What’s there is Kyle Tucker, who’s awesome, and I’d trade Vladito straight up to get him without hesitation. But that’s it. There’s no backup plan. And while the Blue Jays have been in on a lot of top-tier free agents in the 2020s, they’ve never landed the biggest fish in the pond. Having lived through the Ohtani saga two offseasons ago — maybe the most excruciating free agency near-miss in baseball history, all things considered — you’d understand the Blue Jays not wanting to take that risk again.

So what are they left with? Well, an overpay, probably, especially once you figure in the last third or so of this contract. But maybe not by as much as “second-biggest contract in baseball history” would have you believe.

Let’s end by going back to Dan’s article: If Guerrero puts in another season like last year’s, even ZiPS — that merciless, pessimistic, mathematical curmudgeon — has a positive outlook.

“With a repeat of his 2024 season,” Dan wrote. “ZiPS is a lot more confident in Guerrero’s future, adding enough to get to the $400 million mark over nine years, with the rest of his career after that point tacking on another $100 million.”

Under those circumstances, ZiPS would project Guerrero to keep posting wRC+ marks in the 140s and 150s through the end of the decade, and to hit .282/.363/.447 in 2034, his age-35 season. That would be an OPS+ of 126, which is better than what Alonso posted in either of the past two seasons. Most hitters would kill for a decline phase like that.

But most of all, that’s a problem for another day. The Blue Jays locked up their best player for the rest of his career. That’s a huge positive, no matter the terms. They can figure out the rest later.