The biggest move the Blue Jays can make this year isn’t a free agent signing — especially now that Juan Soto is off the table. The most important negotiations for Ross Atkins and company will center around Vladimir Guerrero Jr., the team’s superstar first baseman who’s months away from walking to free agency.

I know fans are calling for an extension as soon as possible — heck, they’ve been clamouring for a deal for years. But, if it happens, when will that extension realistically happen? What are the variables and motivations that impact that timeline?

The Blue Jays dropping a Vladdy extension in the next few days would soothe the sting of an off-podium finish in the Juan Soto sweepstakes. But, I’d be shocked if it came soon.

Ross Atkins spoke to the media yesterday at the Winter Meetings in Dallas, Texas, and was questioned on the subject, “We have to stay disciplined to how we view things… We are committed to always being fair and being consistent. Nothing has changed in terms of our pursuit of Vladimir Guerrero Jr., and we are very hopeful to extend him.”

It takes two sides to agree. What incentive does Guerrero Jr. have to ink a long-term deal in December? He doesn’t know what the Blue Jays’ roster will look like in March, let alone for the potential decade he’d be committing to Toronto. Is he signing on to a core that includes Teoscar Hernández and Corbin Burnes? Or is he signing away his prime with no long-term, high-level pieces around him?

Of course, the Blue Jays could put a massive dollar figure on the table today and get it done, but I figure Guerrero Jr. wants to see what the rest of Atkins’ offseason looks like before really heading to the negotiation table. The Jays probably want to see how these next months go, too, as a few more free-agent misses could signal an impending reset.

As well, I don’t think the gargantuan amount of money Soto just signed for should be discounted here — it has a trickle-down impact. The newest Met is obviously not a one-for-one comparison to Guerrero Jr. Still, I do think the contract has shaken up Vladdy’s negotiations and the rest of the baseball landscape.

Both Vladdy and the Blue Jays will be eager to see what guys like Alex Bregman and Pete Alonso now get in free agency — as they may also earn well north of projected contracts, like Soto. If this winter is filled with other massive deals, it’s a sign the market is shifting and Vladdy’s extension ask would push up with it.

In my view, this is Toronto’s best path to locking up Vladdy.

The Jays did extend José Berríos in November 2021, but this front office has done most of its extension and arb negotiation work in Spring Training, historically speaking (Bo Bichette in 2023, Randal Grichuk in 2019). In fact, members of Toronto’s front office have explicitly told me they don’t like negotiating deals once the season starts. So, I see the start of the 2025 season as a pseudo deadline for a deal.

Spring is the time when both sides know exactly what they need to know — it’s also a time filled with optimism, usually. Guerrero will know how Toronto’s offseason panned out and what the future could hold and the Blue Jays know the state of the market — both know how much comparable players signed for and the potential destinations for Vlad the next year in free agency.

The Jays better take a real shot at this extension in spring, though. If Opening Day kicks off and Guerrero is still a pending free agent, Jays fans can look to Shohei Ohtani and Juan Soto as a signal of what’s likely to come next.

If the Jays don’t get a deal done before Opening Day, Guerrero’s pending free agency will become one of the biggest stories of the regular season. Of course, Toronto could ink him to a deal during a random road trip to Texas in July. But, at that point, it’s more likely he gets to the open market if things aren’t tied up by the end of March.

In November, it’s no longer a negotiation — it’s a bidding war. The scorned Yankees will be in, the ambitious Red Sox have long-coveted Vlad, and maybe Steve Cohen will decide to drop his massive wallet on the table once more. This is the worst-case scenario, and every day that goes by without a deal announced, it’s an increasingly likely reality.

Even if Vlad, ultimately, wants to return to Toronto, there’s a case he should wait until next winter anyway. That’s exactly what Aaron Judge did two years ago, and he earned ~$150 more than the Yankees were offering before Opening Day.

The Jays have one way to prevent getting to this point (well two, if you consider the scary possibility of a trade): the big offer. They can make it now or they can wait until Spring Training, but If the Blue Jays want to keep their star first baseman, the clock is ticking.