For a franchise that possesses 27 World Series titles, it’s been a while since the New York Yankees have captured championship gold. The last time the Yankees were victorious in the Fall Classic, they defeated the Philadelphia Phillies in six games back in 2009. This year’s loss to the Toronto Blue Jays in the AL Division Series (ALDS) was yet another disappointing ending for a team that prides itself on the number of titles it has captured throughout the club’s history.

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There are a few holes that Yankees GM Brian Cashman and the front office need to address. Most notably, the potential loss of outfielder Cody Bellinger in free agency leaves a hole in left field. While the hope is that Jasson Dominguez continues his development and claims that spot, Cashman would surely like to hedge his bets.

While re-signing Bellinger or inking another free agent, like star outfielder Kyle Tucker, could be an expensive proposition, trading for a replacement could be wiser. There are several avenues in which Cashman can explore the left field spot. However, one idea that has gained a lot of traction since first suggested a few weeks ago would be Cleveland Guardians left fielder Steven Kwan. Luckily for the Yankees, they have a player who could be offered in a straight one-for-one swap. That player? None other than top outfield prospect Spencer Jones. Would that be enough to bring Cleveland to the table?

Spencer Jones could unlock multiple trades for the Yankees

Scranton/Wilkes-Barre RailRiders outfielder Spencer Jones (48) is walked during the first inning of Game 2 of an MiLB International League Championship Series at VyStar Ballpark Wednesday, Sept. 24, 2025 in Jacksonville, Fla. The Jacksonville Jumbo Shrimp defeated the Scranton/Wilkes-Barre RailRiders 6-4 and force a Game 3 Thursday evening for the title championship.
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Question 1 of 4

Which pitcher struck out 20 batters in a single game?

Nolan Ryan
Roger Clemens
Kerry Wood
Randy Johnson

The Yankees’ lineup really only has one true hole: in left field, where Bellinger once roamed. Furthermore, they could use a prototypical leadoff hitter. A bat that will consistently get on base and give three-time AL MVP Aaron Judge a chance to knock in more runs. Kwan would serve that purpose and more for New York.

Kwan is slated to hit arbitration once again this winter. At 28 years old, he’s scheduled to hit the open market after the 2027 season, as his arbitration years would be done. While the Guardians could lock him in with an extension, he’s likely to prove too expensive for the current owners’ wallets. If that’s the case, don’t be surprised to see Cleveland GM Mike Chernoff and the front office to consider trading their leadoff hitter.

Despite the fact that Kwan is only a couple years from the open market, the Guardians won’t move him for peanuts. It would cost a pretty penny for the Yankees, or any other team, to pick him up. Luckily, a piece like Jones could be a major part of a return for Kwan. The center fielder shot through New York’s minor-league system, finishing the season in Triple-A.

While his strikeout totals are a bit concerning, an organization like the Guardians could certainly help the towering outfielder change those tendencies. If Cashman decided to trade Jones, plus another piece, like a pitcher such as Harrison Cohen or Thatcher Hurd, that could be enough to bring Kwan into the fold. Would it be worth parting with those pieces for the Yankees? If they hope to get back to the World Series, they need to try and bring Kwan aboard, whatever it takes.