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William Contreras trade could elevate the energy of Yankees-Red Sox rivalry

This could kick things up a notch.
ByStephen Parello
Oct 3, 2026; Milwaukee, Wisconsin, USA;  Milwaukee Brewers catcher William Contreras (24) reacts to hitting a solo home run during the seventh inning against the San Diego Padres in game one of the NLDS for the 2026 MLB Playoffs at American Family Field.xx.  Mandatory Credit: Michael McLoone-Imagn Images
Oct 3, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers catcher William Contreras (24) reacts to hitting a solo home run during the seventh inning against the San Diego Padres in game one of the NLDS for the 2026 MLB Playoffs at American Family Field.xx. Mandatory Credit: Michael McLoone-Imagn Images | IMAGN IMAGES via Reuters Connect

One of the New York Yankees prime trade deadline needs was believed to be the catcher position. It seemed like a foregone conclusion that the club would target help behind the plate, as Austin Wells struggled miserably throughout the first half of the season. Brian Cashman seemed to feel otherwise.

Wells rebounded somewhat in the second half, hitting .229/.351/.436 down the stretch. Still, the Yankees might not want to roll into 2026 with Wells, or at least might be wary of counting on him as the primary catcher moving forward. There will be options in free agency, highlighted by Ryan Jeffers, but after him there's Tyler Stephenson and a bunch of questionable options. The bidding for Jeffers could get hot, so New York might turn to the trade market to scratch its itch behind the dish.

That could bring a risky trade partner back into the fold: the Milwaukee Brewers, who could find themselves dangling William Contreras in order to bring back a haul.

Trading the soon-to-be 29-year-old would follow the Brewers' M.O. He'll be entering his final year of team control in 2027, and his last two seasons have been good, but a downgrade from his peak in 2023 through 2024. This season, Contreras hit .270/.341/.417 with 18 homers, which is good production regardless of position, but looks even better in light of the fact that he's a catcher

William Contreras fWAR by year since becoming a regular

2023 - 5.8

2024 - 5.5

2025 - 3.7

2026 - 3.0

A Yankees-Brewers William Contreras trade would be a Devin Williams type of risk that further ignites Red Sox rivalry

Whether Devin Williams flopped because he was on the decline or because he just didn't want to play in New York is unclear, but Milwaukee has a history of fleecing people in these kinds of trades. Just look at what they did to the Mets with Freddy Peralta for further proof.

There's a real reason to engage the Brewers with caution, even for an offensive force at catcher like Contreras. However, if Brian Cashman made a move for the backstop, he'd be throwing even more gas on the Yankees' never-ending rivalry with the Boston Red Sox.

The Red Sox employ William's older brother, Willson Contreras, so such a move would add a sibling rivalry dynamic to the competition between these long-standing enemies. Willson is fiery player, who has both taken Boston's leadership to task while also threatening to use his no-trade clause if the Red Sox approached him about a trade prior to Boston's turn of fortune ahead of the deadline.

William is an equally passionate player, following in his older brother's footsteps with stirring displays of emotion on the field. Putting the two of them together, on opposite sides of the most heated rivalry in sports, would create a highly combustible situation that could be a lot of fun to watch.

It's all speculation for now. The Brewers have shown no indication that they'd want to trade Contreras, and we'd have to admit that while he'd be an intriguing option, we'd be wary if they actively shopped him. At the same time, if he landed in pinstripes and it worked out, next year's Yankees-Red Sox matchups could be full of fireworks and a lot of fun.

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