Guardians Still Face Massive Looming Question After Trade Deadline

The smoke from MLB’s chaotic trade deadline has finally settled, and the Cleveland Guardians are largely in the same spot they were in ahead of one of baseball’s wildest days.

The drama surrounding the Guardians during deadline day was whether they would, or wouldn’t, trade their All-Star left fielder, Steven Kwan.

After plenty of rumors and speculation, Kwan ultimately remained in Cleveland past the trade deadline, but there’s still one massive question that has to be answered: Will Kwan stay a Guardian long term, or is the organization postponing a trade until the offseason?

Jun 7, 2025; Cleveland, Ohio, USA; Cleveland Guardians left fielder Steven Kwan (38) celebrates after hitting a double during the ninth inning against the Houston Astros at Progressive Field. Mandatory Credit: Ken Blaze-Imagn Images | Ken Blaze-Imagn Images

Let’s be clear, the Guardians don’t have to trade Kwan. He still has two and a half years of team control left and won’t become a free agent until after the 2027 season.

However, Kwan is creating quite a nice resume for himself, and with that, will be do for a large payday once he does hit the open market.

Cleveland’s organization typically doesn’t retain its stars once their first MLB contract is up, unless that player is Jose Ramirez, who decides to take a hometown discount well under market value. Francisco Lindor, Michael Brantley, and Josh Naylor are some recent examples of All-Star position players who didn’t stay with the team long-term.

This reality is why the Kwan trade speculation is already starting to sneak into the mix.

Kwan and the Guardians have reportedly held extension talks in the past few offseasons, but obviously, the two sides haven’t been able to come to an agreement.

It’s not too late for Cleveland to sign their star left fielder, and Kwan clearly is a fan of both the city and the organization.

The Guardians should still aggressively try to sign Kwan to an extension, but if the front office doesn’t feel that he’ll sign the deal they present to him, they could look to move him sooner rather than later.

However, at this point, this is a dilemma that must wait until the offseason.

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