Did Andrew Benintendi contract help Yankees with Ian Happ trade?

The New York Yankees are very familiar with the “price going up,” as fans watched for the duration of the 2022 season when Aaron Judge continued to hit home run after home run in his contract year, eventually earning $360 million over nine years (after they offered $213.5 million over seven).

The Chicago Cubs? Really not sure they’ve ever dealt with anything close to this magnitude. The largest contract in the history of their franchise is Jason Heyward’s $184 million, followed by Dansby Swanson’s $177 million. And those were players outside the organization.

They failed to retain a single player from their 2016 championship core. All of Kris Bryant, Anthony Rizzo, Javier Báez, Jorge Soler, Willson Contreras and others are gone. Whatever they’re doing right now is … directionless, to say the least.

Their current core is Swanson, Ian Happ, Nico Hoerner, Seiya Suzuki, Marcus Stroman and Jameson Taillon? Did we get that right?

And Happ, arguably the best of the group, is a free agent after 2023. Why does this matter? Because after Andrew Benintendi, a fellow left fielder, signed a five-year, $75 million contract with the Chicago White Sox, Happ saw his market instantly reach new heights.

Did White Sox help Yankees in Cubs-Ian Happ trade talks … possibly?

The only difference here is that Happ will be entering his age-29 season heading into free agency, while Benintendi was entering age-28. That’s the best we can nitpick here. Otherwise, Happ is on track to have the edge in more important offensive categories, like home runs, OPS and OPS+.

Happ also has recency bias on his side, as he’s outperformed Benintendi over the last four seasons, with Benny’s 2017 and 2018 campaigns inflating his overall numbers. Additionally, Benintendi’s contract year was hardly impressive. Across 126 games between the Yankees and Royals, he hit .304 with a .772 OPS, 120 OPS+, 54 runs scored, 5 HR and 51 RBI. He had just 31 extra-base hits. His defense? Exactly average. He logged a 0.0 dWAR, 2 Defensive Runs Saved, and 0 Outs Above Average.

Does the Cubs’ reported interest in Michael Conforto indicate they’re not willing to pay up on an extension with Happ after learning it’ll likely cost at least a $15 million AAV deal (or likely more, if Happ logs another All-Star-caliber campaign in 2023)?

Yankees fans have long been on the “trade for Happ” bandwagon, especially after he emerged as a competent full-time left fielder last season (he was previously used all over the diamond to varying degrees of success). The Cubs are not built to win in 2023, so if there’s a gap in possible extension talks, there’s no reason to think Chicago wouldn’t consider a trade.

As for New York, Brian Cashman should be willing to go out of his comfort zone to fill the last missing piece on this championship roster. Bring in Happ and add another reliever, and the 2023 season is looking exponentially better than the last three years.

3 Cubs trade targets Yankees should pursue at 2022 deadline

The New York Yankees should pursue these three Chicago Cubs at the 2022 MLB Trade Deadline to beef up the outfield and bullpen.