If there is one thing you can bet on during the winter meetings, it’s that Brian Cashman won’t sit still; he never does. Whether it was Gerrit Cole in 2019, Giancarlo Stanton before that, or the re-signing of their captain, Judge, the New York Yankees general manager always makes a way to make a noise. This time, too–they might be ready to do something drastic. And the first domino? It might involve the Blue Jays.

Up in Toronto, the Jays have also bulldozed through the early off-season checklist. Dylan Cease to Cody Ponce, both signed. Shane Bieber is back for another run. And they made it crystal clear–they are not slowing down and are running after names like Kyle Tucker, Pete Fairbanks, Edwin Díaz… and yes, Steven Kwan.

And that’s exactly where things start to get messy.

Insider Robbie Hyde says two of those top Toronto targets–Kwan and Fairbanks–could end up with New York instead! And if Cashman pulls that off, he wouldn’t be just derailing the Blue Jays’ off-season strategy; he would be reshaping the Yankees’ future and even putting two young Yankee careers directly in the line of fire.

Right now, the Yankee outfield is crowded, but it is unsettled. Aaron Judge owns right field, Grisham is the placeholder in centre, Jasson Dominguez is on left, and Jones is coming up fast. Hyde thinks that the New York Yankees might be prepping for a move by giving up Domínguez or Spencer Jones—especially if they land someone like Steven Kwan.

It does track because Kwan gives the Yankees exactly what they have lacked for years–a real leadoff hitter who gets on base, puts the ball in play, and gets the job done. He played 156 games for Cleveland last season, hitting. 272 with 11 homers, 56 RBIs, and 21 steals.

Then comes the bullpen, and given that Devin Williams is gone and Luke Weaver is unsigned, the Yankees needed some expert help. This is where Pete Fairbanks enters the picture. He is yet another Jays target and now a real option for the Yankees. Sure, he is showing early signs of decline, but over the last six seasons, he has been the league’s most consistent reliever, ranking top-30 in fWAR, xERA, FIP, and strikeout rate.

But these are not the only smart moves the Yankees could go with!

Minnesota’s fire sale might hand the Yankees their next rotation fix

The Minnesota Twins’ mid-season teardown was one of a kind, where they sent Carlos Correa to Houston, Jhoan Duran and Harrison Bader to Philly, Willi Castro to the Cubs, and Danny Coulombe to Texas. One team not involved in this was the New York Yankees, but that could change.

Minnesota didn’t move everyone, though. Joe Ryan and Byron Buxton are still on the roster… But for how long? Because it feels counterproductive. Why cling to a 70-75 win ceiling? If they want a reset, then mobbing Ryan and Buxton during or after the winter meetings is the logical next step.

This is where the Yankees enter the picture, because Ryan fits perfectly. The New York Yankees need another steady arm, and he fits as a No. 3 or No. 4. Now, Gerrit Cole will eventually return from his Tommy John surgery and take the ace spot, but he won’t be ready for opening day. Max Fried was a brilliant pickup last season, but the rotation needs depth, and they need reliability.

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And Ryan brings both!

This is also where Spencer Jones enters the conversation. The Yankees’ top prospect isn’t untouchable if you thought so. Sure, most people assume he would be moved for a big bat, but a solid starter like Ryan can move the needle. Jones, paired with Carlos Lagrange, could give the Twins two legit building blocks.

What do you think?