Olney: Santander signing could backfire if Jays aren’t able to extend Vladdy

The Toronto Blue Jays filled a major need Monday when they signed power-hitting outfielder Anthony Santander to a five-year deal.

But even though Toronto desperately needed to make a splash after being rebuffed by many of their top targets already, was adding Santander the right move? That depends, according to ESPN’s Buster Olney.

Olney explained that while Santander fills a major need on the Blue Jays’ current roster, it could end up being a contract they’re looking to get out of in short time, depending on how things go the rest of the off-season.

“The micro level, they get a good player who clearly is an improvement over what they had. He’s a power hitter; he adds balance from the left side and he’s known as a good clubhouse guy,” Olney told TSN 1050 Toronto’s First Up Tuesday morning.

“That’s on the micro side. The macro side, I mean, it’s almost like we forecast this in our previous conversation. Like at some point, are they going to wind up overpaying Santander to a contract that in six or eight months they’ll be looking to get out of.”

A 30-year-old outfielder coming off a 44-homer season in 2024, Santander officially signed with the Jays Monday on a five-year, $92.5 million deal that includes an opt-out clause and a 2030 team option with escalators and deferred money.

According to Olney, it’s a deal that makes a lot more sense if star first baseman Vladimir Guerrero Jr. is signed long-term.

“If they don’t sign Vladimir Guerrero Jr., okay, and they’re forced into a decision at some point in the next six months to trade him, what you’re going to have at the end of the year is potentially the same problem – not really having the core guys locked up – and now you have [Santander] signed to a long-term deal that clearly other teams don’t want to give him. The order of operations needs to go backwards.

“...If you sign Vladimir Guerrero Jr., if he does agree to sign, then that’s to me when you go after Santander. That to me is when you’re like, okay, we’ve got the centrepiece, now we’re going to get the complimentary pieces because the way it could play out if they wind up trading Vladdy and having a tear-down, because they don’t look like they’re close to competing in the American League East, then what does that Santander contract look like?”

Set to be a free agent at the end of the season, Guerrero reportedly rebuffed previous contract offers from the Jays this off-season. Reports indicate Guerrero conveyed to the Jays he had no interest in negotiating an extension past the first day of spring training.

“From what I heard last week, the Mets desperately want Vladimir Guerrero Jr. They want him. They’re got a core of surplus position-player prospects that they’re going to have to sort through in the next couple of years. They’re actually well positioned to talk about a trade for someone like Vladimir Guerrero Jr.,” Olney said, adding that he believes the Jays will have to trade their franchise player if they can’t come to a long-term agreement.

“Move on and start to build on what you’re going to have going forward as opposed to, you know, it always feels like they’re a day late and a dollar short all the time. Make an aggressive move in that direction.”

Another course of action for Toronto, according to Olney, would be to sign free agent first baseman Pete Alonso to help them in 2025 and be a possible contingency plan if Guerrero leaves or is traded.

“Well, you know what, if Vladdy’s not going to sign, if he’s not going to be the core guy, then sure. Trade him for prospects, sign Pete Alonso, sign Santander and build your bridge into the future.”
Olney told TSN 1050 the Jays are in a “great position” to sign Alonso because of his current market.

“… If the Mets move on from him, then I mean, let’s face it, the Blue Jays’ best chance for signing guys is to overpay veterans who are not getting the money they want elsewhere. And Pete Alonso doesn’t have much of a market. So, it wouldn’t surprise me if they work out something there.”

But ultimately, according to Olney, the Jays’ future all comes down to getting Guerrero signed long-term. And only then will Santander’s deal and anything else the Jays do this off-season come into clearer focus.

“There could be more work [to do in free agency] but I still think that you have to look at the team if you’re the Blue Jays through the prism of how close are we to the Yankees, to the Red Sox, to the Orioles, and right now, they’re not close,” he said.