How much is a championship-winning third baseman worth when his best days are behind him? For super-agent Scott Boras, the offseason isn’t just about landing the biggest contract; it’s about playing chess with MLB rosters, even if that requires pushing Alex Bregman away from an established team like Boston. And one potential landing spot, the Toronto Blue Jays, could create a domino effect that puts the future of a promising young player in jeopardy.

According to Jim Bowden, Bregman could end up in Toronto.

“There are several contending teams that Bregman would be a difference-maker for if he signs with any of them, including the Tigers, Phillies, Mariners, Yankees, Mets, and Blue Jays, as well as non-contending teams like the Angels and Pirates. His free agency is going to be must-watch during the Winter Meetings.”

While Bregman leaving Boston and going to the next best place sounds appealing, a closer look reveals it’s not without risk. Bregman is entering the stage where the production historically begins to dip. He is turning 31 this March, and only nine players of this age or older have posted a 4+ WAR in 2024. Most were better hitters than Bregman.

Add in his declining walk rate of 6.9% last season, and we see a hitter’s once biggest weapon slipping past. His athleticism, too, has followed a similar path: below-average speed, a declining arm, and the elbow surgery raise questions about his durability.

Plus, let’s not discount that profile leaving Fenway’s friendly dimensions to go to Rogers Centre, a completely new environment, and a place that could mute his resurgence. Moreover, his signing with the Jays could crowd the infield built around Bo Bichette and create a spillover effect the Jays don’t want.

Then there is the obvious Scott Boras layer.

Bregman is clearly betting on himself, all thanks to Boras’ hype. He is pursuing a long-term deal that pays him like a star into his mid-30s. This gamble could get expensive fast on both sides.

Meanwhile, Bowden’s analysis puts Addison Barger in a difficult position, as well.

The Jays are already juggling a chaotic winter. They are trying to figure out what to do with their pursuit of Bichette, while also monitoring Kyle Tucker’s megadeal market amid staying afloat the Ketel Marte trade rumors.

Adding Bregman into the picture, someone who is a steady bat and a proven postseason player, will force Toronto into making an uncomfortable decision: someone has to move. This is where Barger’s future becomes uncertain.

Already for weeks, analysts have hinted that Barger could be the piece Jays part with if they pursue Marte.

On Locked On Blue Jays, Brayden Ewasko put it plainly: “If they do get Bo Bichette, they’re probably not getting Kyle Tucker… And so in that situation, you’re alright giving up Addison Barger.”

Toronto’s financial math makes it even trickier.

Bichette could cost over $200 million, Tucker might command $440 million, and Marte’s contract runs through 2028. And even after a dip, Bregman has proven to be a .275 career hitter with a 133 wRC+. So he won’t be any less expensive. And again, he’s a Boras client – they won’t settle for less.

But does Alex Bregman even fit with the Toronto Blue Jays?

Insider reports aren’t always set in stone. A-Breg is one of the most intriguing names in free agency, but the truth is, he comes with equal parts upside and uncertainty. He is no longer the player who tore the league apart back in 2019 with a .296/.423/.592 line, but he’s still betting big and aiming high.

And as far as the connection with Jays goes, it’s not as wild as it sounds.

The Toronto Blue Jays already have a strong defensive option in the infield. Ernie Clement, Andrés Giménez, and others can pick it clean. But what they don’t have is the steady offensive production that Bregman, even in a down year, can bring.

ESPN has projected that Alex Bregman could get a five-year, $160 million deal this offseason, and that price point alone tells you that the teams see him as a reliable bat.

But Bregman’s defense is questionable. His glove is not what it used to be. If he can’t return to his 2018-19 form, the Jays could be paying premium dollars for some average leather – that’s a huge gamble.

So, will Toronto take the bet? Because his impact and leadership are definitely something to consider.