RISKY BUSINESS: What are the Blue Jays getting from $500-million investment in Vlad Guerrero Jr.?

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The money figure had been tossed around for weeks and months now: $500 million US — or more than $710 million in the currency of the country Vladimir Guerrero Jr. was born.

The fact that the Toronto Blue Jays finally got the face of their franchise under contract for a near-unfathomable 14 years is both a landmark deal and one that has risky implications far beyond the moment and far beyond Canada’s lone Major League Baseball team.

What does it mean to the future of the Blue Jays, a last-place team doggedly determined to spend aggressively to remain competitive and thus relevant?

What is the context of the richest deal in Canadian sports history when compared to other franchises?

And what does it mean to free-spending telecommunications behemoth Rogers Communications, which suddenly seems to care more about sports than bloated wireless plans?

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We answer these questions and more in explaining the questions surrounding the enormous deal that was finally agreed to in the wee hours of Monday morning.

PLAY WITH THE BIG BOYS

Simply put, the Blue Jays finally got their man.

In losing out on high-stakes (and high-visibility) bidding wars for superstars Shohei Ohtani and Juan Soto in the past two off-seasons, respectively, the Jays front office was getting a reputation as the Toronto Bridesmaids.

That didn’t deter president Mark Shapiro, with the bankroll and blessing of Rogers Communications CEO Edward Rogers, from pushing in his chips at the big-boy table, however.

“We are not going to apologize for competing for the highest level of talent,” Shapiro said in an interview with the Sun last month. “The fact that we were in and one of the two final teams for some of these great players, to me means that there’s a recognition across the game that Toronto is a world-class city and that it’s a great place to play.

“I’m not going to shrink from that narrative. We’re going to continue to compete for the best talent in Major League Baseball. And I just believe that if we keep after these guys, there absolutely will be a guy we get.”

And now they’ve got their man. The fact that the Jays landed a home-grown player — and one born in Montreal, where his father was on his way to a Hall of Fame career with the Expos — is a bonus.

It also serves notice to future free agents that the Jay mean business — big business — and are determined to pay to build and sustain a winner around the corner infielder and cornerstone player.

ROGERS RICHES

Even by Rogers Communications’ free-spending ways in the sports sphere, dropping $500 million US on one player is a serious commitment, both to win and show good faith to a fan base already antsy about the team’s immediate and long-term future.

This is a company, after all, that dropped $11 billion to lock up broadcasting rights for another 12 NHL seasons and essentially seize control of the Canadian hockey market.

The company also is buying out rival Bell’s share in Maple Leafs Sports and Entertainment, giving itself unprecedented investment and control in the Canadian sports scene.

For the past three seasons, the Jays have been among the MLB leaders in payroll spending. Under Shapiro’s watch, the club also has paid somewhere in the neighbourhood of $500 million for upgrades at the Rogers Centre and the team’s player development complex in Dunedin, Fla.

Is there no bottom to the money Rogers is willing to spend on its sporting endeavours? It doesn’t appear so.

ALL-IN TO CONTEND

By locking Guerrero up for the remaining peak seasons of his career and beyond, the Jays slammed the competitive window back open.

The presence of the big-hitting first baseman will no doubt be a huge attraction to future free agents while also creating further good will from the fan base. It should also encourage players on the roster to consider signing extensions, given the commitment to the team’s most famous player.

What does all this add up to? In theory, anyway, it suggests the Jays will have an easier time accumulating assets to be competitive than they would had Guerrero walked to free agency after the 2025 season, a prospect that was looming large.

From the time he made his major league debut to this historic contract agreement, Guerrero has been seen as the type of player to build a franchise around. It certainly could be argued that the Jays front office had grossly misplayed an asset of this magnitude by letting him get this close to free agency.

Instead, Guerrero will be associated with the Jays for this generation of fans and the one to follow.

CANADIAN CONTEXT

The $500-million US deal is mammoth on so many levels, eclipsing the amount by a wide margin that any NHL or NBA player makes in the country.

At $13.25 million US, Auston Matthews makes more money than any NHL player this season. Edmonton Oilers star Leon Draisaitl’s eight-year, $112-million deal is the richest in total value, however.

With the NBA, the $225 million Scottie Barnes is making on a five-year extension tops the Raptors payroll.

In terms of present-day value in baseball, the $500 million deal is second only to Juan Soto of the Mets, who with his 15-year, $765-million contract tops the MLB gourmet food chain.

The Guerrero deal (which is pending him passing a club physical) also dwarfs — more than doubles, in fact — the previous amount paid for a first baseman, topping the $240 million over eight years the Detroit Tigers committed to Miguel Cabrera.

WIN-WIN?

Deals of this magnitude rarely can be graded in the present, with so much term and so many variables to unfold.

In the short-term, however, perhaps both “sides” can claim victory.

For the Blue Jays, they finally found someone willing to take an historic contract — one that was more than triple the size of the $150 million it shelled out for six years of outfielder George Springer’s services in 2021, the previous club high.

As mentioned above, securing Vladdy should help market to both fans and future free agents, not to mention have one of the game’s most dynamic hitters in the lineup on a nightly basis.

On a broader scale, the team had little choice (a fact Guerrero was well aware) to get a deal done in the early days of this season at the latest. The risk was simple: Sign him to an extension or let him walk.

For Guerrero, holding firm on his contract demands — and not wavering from his want of $500 million without deferrals — was seen by some as a bold move. But the player and his camp had trust in both his ability, his negotiating leverage and the fact that being the darling of next winter’s free agency were all money cards in his hand.

By playing his hand this way, it appears that Guerrero landed himself another $50 million, the gap that had previously existed between the two sides.

Another factor that may have played into the Jays desire to ensure Guerrero didn’t get away? Shapiro said there has been a recognition of his commitment to work on his fitness to maximize his considerable talents.

“There’s a maturity in his role as a teammate and there’s a maturity in his approach to going about his business,” Shapiro said.

DID SOMONE SAY PLAYOFFS?

Ah yes, the post-season is somewhere between a dirty word and a curse around this team. The Jays have made it to the post-season three times in the Guerrero “era,” but have yet to win a single game.

Last year, of course, it bottomed out with a 74-88 record that plunged them to last place in the American League East.

A competitive window that those results suggested is closing, is very much open — at least in the view of those running the franchise.

There is belief in the starting rotation (even with Max Scherzer injured), belief in the elite defence and faith that the offence will be more versatile and productive than the leanness of the past three seasons.

The blueprint, then, is to contend for a playoff spot sooner rather than later and have the revenue reaped from those dates help defray the cost of keeping Guerrero in the fold.

PRESSURE’S ON

There is no denying the talent in Guerrero, a fact acknowledged by baseball personnel around the game.

His 48-homer breakthrough in 2021 validated those opinions while also heaping more onto the weight of expectations. After sub-par and inconsistent seasons in both 2022 and 2023, there was a Vladdy revival in 2024, one that heightened the urgency to get something done.

Now, much will be expected of Guerrero — who has yet to hit a home run in his first 10 games this season — but has had tepid starts in the past.

A happy-go-lucky player by nature, Guerrero also is driven to have a huge season. In that sense, he has matured and grown over the past three years, no longer the fun-loving teen who smashed baseballs almost for his own amusement.

The pressure to produce gets amped up, starting with a four-game series at historic Fenway Park (where Guerrero has hit 10 career homers, a handful of them prodigious) on Monday night.

WHAT’S THE ROI?

It’s near impossible to handicap the potential of monetizing such a bloated contract, one that undoubtedly is factoring in a dramatic downturn in production and impact for the waning years.

Guerrero is popular with the fan base, though, and is a draw unto himself. And he certainly helps the prospect of winning, which is how Shapiro believes the bottom line is most affected.

“I think the monetization comes from winning,” Shapiro said in our interview. “I’ve never seen fans come to see great players on the losing team. Very few fans do that. We’ve got to win. It’s a lot easier to win with great players like Vlad and Vladdy has a magnetic personality that he has a chance to amplify (those chances.)”

In that regard, the business case for Guerrero is significantly different than that for Ohtani. The Japanese and global superstar, for example, opened a huge potential revenue stream as a marketing entity of his own.

With no deferrals, as Guerrero insisted, and no opt outs, the risk lies with the team not the player.

Given that the contract doesn’t include this season — it kicks in for 2026 — I guess we’ll find out a decade and a half down the road.

Wrapping your head around that time frame is as difficult as the dollar value.