The Blue Jays need to sign Bo Bichette to this proposed deal at the Winter Meetings

The 2025 Winter Meetings are just around the corner and if the first month of the offseason is any indication, there could be lots of news coming out of Orlando beginning next Monday. Or, it could be a total let down and nothing of significance happens. Regardless, these meetings are a time for GMs to at least get together and lay some ground work face to face with other GM's, agents, and players.

One former MLB GM is hoping that this year's meetings are, in a word, chaotic and he predicts that the Blue Jays won't be immune to the chaos. Jim Bowden recently wrote an article for The Athletic with his Winter Meetings wish list, and on that list is a reunion between the Blue Jays and their home grown star, Bo Bichette.

The Blue Jays need to sign Bo Bichette to this proposed deal at the Winter Meetings

Within Bowden's article, the insider says one of the things he would like to see happen is that Bichette and the Blue Jays come to terms on a seven-year, $189 million deal. He writes, "A Bichette reunion would allow the Blue Jays to run it back and keep the Vladimir Guerrero Jr./Bichette combination for years to come. Bichette wants to be there and they want him there — let’s get it done."

Sounds simple enough! That dollar figure and term pale in comparison to the 14-year, $500 million that Guerrero got. It's also lower than what some of the other marquee shortstops got on the market in the last few years by both total dollar figure and years, but it might be the best deal Bichette gets on the market with an Average Annual Value (AAV) of $27 million.

Some of the other recent deals include Carlos Correa who got a six-year contract from the Twins for $200 million, an AAV of $37.3 million. Corey Seager landed a 10 year deal worth $325 million from the Rangers with the AAV at $32.5 million. Francisco Lindor got a 14-year deal done with the Mets for $340 million, running his AAV to $24 million, and Trea Turner is locked in for 11-years with the Phillies at $300 million, a $27 million AAV.

There are reasons to like Bichette more than some of those players, but there are also reason's why some teams wouldn't trust Bichette to deliver at that level either. When he's healthy, he is one of the best pure contact hitters in the game. But staying healthy has been an issue the last two years now.

One was a freak accident when he collided with a catcher on a play at home plate - but his speed had diminished even before then, and by all the defensive metrics, his glove work just isn't at the top of the heap in the majors, though recent reports indicate he is very open to making the switch to either second or third base. But even if he's willing to move positions it still makes sense that teams would be shy about going to double digits in terms of the length of the contract. Other teams might even be willing to go to a shorter term, for a higher AAV, but we don't know if Bo would be willing to take that kind of deal.

What we're left with is this; a reasonable prediction for a very talented player who has a few flaws in his game, but nothing that he hasn't proven he can't overcome. That prediction also keeps Bichette with the only organization he has known, which has also been widely speculated across the industry to be the best fit. If the Blue Jays come out of the Winter Meeting with Bichette locked up to a deal like this, it will be a very productive week in Orlando.