Could Yankees Trade for Cubs' Ian Happ After Departure of Benintendi?

The Chicago White Sox agreed to terms with free agent Andrew Benintendi on a five-year, $75 million contract Friday, prying him away from the New York Yankees. The Yankees have a need in left field, so would a trade for Ian Happ make sense? Jack Vita ponders.

The Chicago White Sox agreed to terms with free agent Andrew Benintendi on a five-year, $75 million contract Friday, prying him away from the New York Yankees, after the outfielder played just 33 games for the Bronx Bombers, after the club acquired him at the trade deadline.

After a dismal season from Aaron Hicks, the Yankees could use another outfielder. Oswaldo Cabrera saw time in left, but I would be surprised if the club did not add at least one more outfielder before the end of the winter.

The club has engaged in trade talks with the Pittsburgh Pirates pertaining to Bryan Reynolds. Reynolds is under club control through 2025. The price for Reynolds will not be cheap, though, and executive Brian Cashman has recently demonstrated a hesitance to part ways with top prospects.

There may be a cheaper option.

The Chicago Cubs were listening to offers from opposing clubs at the 2022 MLB trade deadline on left fielder Ian Happ. With one year remaining on his contract and three top-100 outfield prospects in the Cubs' farm system, Happ might not fit into the club's long-term plans.

The Cubs are at a crossroads. They can either extend Happ, re-sign him a year from now, or trade him, instead of letting him walk for nothing.

The left fielder is coming off the best season of his six-year MLB career. Happ received a trip to the All-Star Game and a Gold Glove in 2022, after slashing .271/.342/.781.

As a switch-hitter, he could be a useful pinch-hitter, platoon player or potential everyday left fielder for Aaron Boone. With one year remaining, Happ won't warrant the same type of prospect haul that Reynolds would. The Cubs could add another prospect or two, and give Christopher Morel and Nelson Velazquez more reps in the outfield this season. It would give them a chance to evaluate both players to see if one or both will fit into the club's long-term plans.

Happ could be reunited with former teammate Anthony Rizzo, and compete for a championship before testing the free agent waters next winter.

The Cubs listened to offers on Happ at the deadline, but there are no recent reports on the Cubs shopping Happ this winter.

The Cubs just signed Cody Bellinger to a one-year deal, and have Seiya Suzuki under contract through 2026. Top prospect Brennan Davis could arrive at the big league level in 2023, meaning that the Cubs would need to open a spot for him to play everyday and develop.

MLB.com's Mark Feinsand listed Happ as a potential trade chip for the Cubs at the start of the offseason, writing that:

"It was somewhat surprising when Happ wasn’t dealt before the Trade Deadline, but with one year remaining until he becomes a free agent, the Cubs could look to move him this winter. Happ earned $6.85 million in 2022 and is entering his final year of arbitration, so barring an offseason extension, the outfielder is likely to start '23 in a new uniform."

At time of publication, there were no new scoops on Happ's availability, but as the free agent outfield market begins to dry up, clubs with outfield needs will look to add via trade, and the Cubs could be receiving some calls soon.

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