Cleveland Guardians send:
OF Steven Kwan (arbitration eligible in 2027)
Chicago Cubs send:
RHP Jaxon Wiggins (Triple-A prospect)
UTIL James Triantos (controllable through at least 2032)
Steven Kwan made $7.725M in arbitration for 2026. His 2027 salary is very likely to climb north of $10M.
And, well, unless it’s for José Ramírez, the Guardians don’t like dedicating eight figures to an individual player’s salary.
At any rate, two winters ago, they traded away the final five seasons of their seven-year contract with Andrés Giménez, and subsequently shipped Josh Naylor to Arizona, rather than paying what ended up being a $10.9M salary in his final year of arbitration eligibility.
Despite their penny-pinching ways, they just keep making the postseason, winning the AL Central for the seventh time in 11 years.
So, if they can turn one year of Kwan into a pair of former second-round picks, history suggests they probably will.
On the Cubs’ side of this one, they are losing a boatload this winter, including four of the six players who appeared in at least 20 games in the outfield in 2026. Pete Crow-Armstrong in center is a fantastic starting point, but Matt Shaw in right and either Justin Dean or Kevin Alcantara in left figures to be the plan as currently constructed.
“Losing a boatload” does also mean “has money to spend.” But trading for one year of Kwan at $10M-$12M would allow them to do their real spending on the pitching staff, where they need it most.
Though Kwan is nowhere near the home run threat that Happ is, his career .739 OPS isn’t drastically different from Happ’s mark of .772 over the past five seasons. Both left fielders also won Gold Gloves in each of the past four years, so it could be quite the seamless transition.
On the prospects front, Jaxon Wiggins entered 2026 as a top 100 prospect on Baseball America, Baseball Prospectus and MLB, but he was a mess at Triple-A Iowa, walking nearly 20 percent of batters faced. Maybe Cleveland can fix his command, though, while James Triantos has .300 batting average / 30 stolen bases potential to replace Kwan.