After days of rumors — and months of negotiating — the Toronto Blue Jays agreed to a 14-year, $500 million deal with superstar Vladimir Guerrero Jr. on Sunday night.

The deal is the third largest in MLB history — behind Shohei Ohtani‘s with the Los Angeles Dodgers and Juan Soto‘s with the New York Mets — and, like Soto’s, contains no deferred money. And after finishing as also-rans in both of those deals (along with others) over the past few offseasons, with Guerrero, the Blue Jays receive a long-term commitment from their best homegrown talent since Hall of Famer Roy Halladay. The 26-year-old Guerrero is a four-time All-Star, 2021 American League MVP runner-up and Canadian-born superstar.

ESPN MLB insiders Jorge Castillo, Bradford Doolittle, Buster Olney and David Schoenfield weigh in on the deal.

What is your first reaction to Vlad Jr. agreeing to a $500 million extension with the Blue Jays?

Castillo: It’s about time. Is Guerrero the perfect player? No. But he is a 26-year-old Canadian-born homegrown superstar and the son of a Hall of Famer who wants to stay in Toronto. The Blue Jays will never have another player like this again. For a franchise that has failed to attract stars north of the border — over and over and over again — this is the right move, even if it could become an uncomfortable overpay on the backend.

Doolittle: Mild surprise. It’s one of those things where you’d think that if it were going to happen, it would have happened already. But it’s a smart move for Guerrero. It’s a good franchise, a great city, and he has a chance to be a defining player for it. He could have done it elsewhere, but I’m not sure he would have proven to be quite the market-mover in free agency as he might have thought. His worth was more for Toronto than for other clubs, but he was going to get paid either way.

Olney: The Jays had to do this because by constantly deferring decisions about his situation, they gave him all the leverage — and wow, they paid for that mistake. No deferred salary, $500 million guaranteed. Stunning. But at least for now, the perception of the franchise will shift because the Jays have their anchor — a Canadian-born superstar who wants to stay.

Schoenfield: It’s a little risky at this price point, given Guerrero’s year-to-year inconsistency, but the Blue Jays had to make this move. For them to contend in the AL East, they need the superstar version of Guerrero to anchor the lineup. That’s no guarantee, but there’s also a chance his best seasons are still ahead of him — and they won’t be coming for the Yankees or Red Sox, two teams who likely would have pursued him in the offseason.

What should Toronto’s next big move be after locking up the face of the franchise?

Castillo: Nothing, for now. The Blue Jays should stand pat and see where this team goes over the next three months. If it’s a real American League contender, the Jays can try adding for the stretch run at the trade deadline. If not, they can trade veterans for future help. Guerrero is 26. There’s some time to build a contender around him. A half-measure will only waste more of his prime years.

Doolittle: Let’s let things play out this season and see how the roster functions in what should be a highly competitive division race. This extension establishes the franchise’s longer-term direction, which is to try to win. If Guerrero had walked, the direction would have been a lot less clear, with a full reset on the table.

Olney: It’s hard to say because if they don’t contend, they could be a seller in midseason. The extension for VGJ makes it easier for them to make that decision leading up to the trade deadline.

Schoenfield: I’d start hounding the Marlins about Sandy Alcantara. If the Blue Jays are going to contend this season — and they can — they’ll need more pitching, especially with Max Scherzer’s immediate future in doubt. Alcantara is signed through 2027, so he would team up nicely with Guerrero while showing the Blue Jays are committed to winning now.

If you were starting a team, where would Guerrero rank among the players you would choose to build around?

Castillo: In the top 20. Where exactly depends on if we’re talking about just this season or for several years. Guerrero’s potential at the plate is matched by just a few of his peers, but he has been inconsistent year-to-year and he’s a first baseman who provides little value in other areas.

Doolittle: Second tier, probably in the 15-to-30 range. Positional value, fielding acuity, slowness afoot — all these undercut his allure if you were picking from the entire talent pool, not just in right-now value but for what they mean as he gets older. Not a slam at all — I love to watch Vlady hit and he’s a championship-level producer.

Olney: He’s a great young hitter. Still, given that he’ll be a first baseman or DH throughout the contract, it’s hard to compare him with Bobby Witt Jr. or Ohtani. He’d be in the top 20 for me. Part of the reason he got so expensive for the Jays is what he came to represent about the team’s future, in the eyes of the fans.

Schoenfield: I’d agree with my colleagues. Probably closer to 30 than 15 because I can’t ignore that 1.8 WAR in 2023. The 2024 version of Guerrero is extremely valuable, but he needs to hit at that level given his lack of an all-around game.

Which young star could be the next to land a megadeal like Guerrero’s contract?

Castillo: The answer would’ve been Gunnar Henderson or Elly De La Cruz — if their agent wasn’t Scott Boras, who has a track record of preferring to take his star clients to free agency. With that, Heliot Ramos isn’t on Guerrero’s level — and he surely wouldn’t get a “megadeal” — but he’s a budding star whom the Giants could lock up as part of their long-term core.

Doolittle: Somebody from the Orioles. Shouldn’t they lock up somebody? Henderson strikes me as the kind of player you’d like to have for as long as possible, but he’s not the only one in that organization who fits that bill (no pun intended).

Olney: Elly De La Cruz.

Schoenfield: The window might be closing for a De La Cruz extension with the Reds, but I’d love to see Cincinnati lock him up like the Royals did with Bobby Witt Jr.

Besides the Blue Jays, who is the biggest winner — and loser — of the deal?

Castillo: Guerrero is the biggest winner. When Guerrero is going right, he’s one of the most dangerous hitters in the sport. Look at his 2021 and 2024 seasons. His production in the two years in between, however, was not on that level. Guerrero was very good — and an All-Star — in 2022 and 2023, but he slashed .269/.341/.462 with 58 home runs and 5.8 bWAR across the two seasons. First basemen with those numbers — and poor defensive and baserunning value– don’t warrant megadeals. But his potential and age combined with the Blue Jays’ unsuccessful search for a foundational superstar and Juan Soto’s market-setting deal, created the perfect storm to make this not only possible, but the right move for Toronto.

Doolittle: Jays fans, which isn’t probably what we’re going for here, but this is a big day for them. Toronto has had several really good teams, won a couple of World Series, and had some Hall of Famers pass through their clubhouses. What they haven’t had is an all-time face of the franchise, a Hall of Fame player who spent all or virtually all of his career with the franchise. Dave Stieb is probably the closest thing to that the Jays have had and he was terrific, but Vlady has a chance to become the Blue Jays, even if in a few years the Angels sign him to an erratic, ill-advised contract for his last couple of years. This stuff matters to the identity of organizations.

Olney: Vladdy wins, big-time. The Jays lose in terms of the market because this might be more than other teams would’ve paid, but they win because they desperately needed a signature star to bridge into the future. The Mets were interested in talking about a possible trade in the winter, but sources say they were uncertain about whether to pursue him in the upcoming winter.

Schoenfield: I’ll throw in a couple of losers here — those teams where Guerrero could have been a great fit in 2026. That would include the aforementioned Yankees (Paul Goldschmidt on a one-year deal), plus the Giants (pursuing a big star for years) or maybe the Tigers (plenty of payroll room).

What does it say about the state of MLB to have three players with deals for at least $500 million over the past 15 months?

Castillo: It says teams willing to spend the money have decided paying top dollar for superstars is worth the risk, a departure from where things stood five years ago when the Red Sox traded Mookie Betts instead of paying him his worth.

Doolittle: Everybody’s different. Jackson Merrill seems to like his situation and isn’t driven to maximize his check. There might be an undercurrent of CBA-related uncertainty over what might be looming down the line. So get locked in now, as long as the numbers are in the ballpark.

Olney: Some teams have to weigh these whopper investments, but as we learned from the late, great Padres owner Peter Seidler: The franchises worth billions will be OK if they spend big. The Jays are a financially healthy business, and they have now completely altered the perception of what their franchise could look like in the years ahead. Other teams (hello, Cubs!) should take note. If you’re going to buy a baseball team, be prepared to spend money to make money.

Schoenfield: Despite all the angst over long-term local TV revenue, there is plenty of money in the game. Especially if you’re good and set to reach free agency at a young age.