Andrew Benintendi Deal with Sox Provides Starting Point for Ian Happ Negotiations

The Cubs have taken a real will-they-or-won’t-they approach with Ian Happ, who was being shopped at the deadline and now is reportedly the subject of aggressive extension plans. But between the inability to add via free agency and possible fear of being burned again at the deadline, Jed Hoyer could again field calls for his Gold Glove left fielder as he seeks other ways to round out the roster.

Which direction the Cubs choose to take could hinge on Happ’s asking price, which is surely higher now than ever given both his recent hardware and the exploding market. And with just one year of arbitration left, there’s little for the Cubs to buy out in order to get a discounted rate if they indeed want to engage Happ in talks ahead of spring training.

They should have a starting point for those negotiations now that Andrew Benintendi has agreed to a five-year, $75 million deal with the White Sox. Just one month older than Happ and also boasting a Gold Glove in left field with somewhat similar offensive production, Benintendi is about as good a comp as you’re going to find.

Happ has superior power and his ability to bat from both sides gives him additional versatility, plus he’s got more intrinsic value to his current club. Those factors should earn him a little more than his colleague on the South Side, it just depends on how much the Cubs value him as a piece of the next team they may eventually get around to building.

I had mentioned that same exact Benintendi figure as a floor for Happ back in earlier November, so pardon me for a moment while I pat myself on the back. The issue is that Happ’s projected salary of about $11 million for 2023 means he’d only be looking at $64 million of “new” money over the subsequent four years ($16M AAV).

Pushing out to $87-91 million with a partial or full no-trade clause would up the deal to $19-20 million AAV while putting Happ back on the market ahead of his age-33 season. It would also ensure that both corner outfield spots are covered for the next four seasons, which is can be seen as either good or bad depending on your point of view.

The Cubs have a wealth of young outfielders coming up through the system and should need spots for them over the next two years or so. Pete Crow-Armstrong is the prohibitive favorite to hold down center field for years to come, but he’ll have a spot once Cody Bellinger moves on. As for what the Cubs do with Brennen Davis, Alexander Canario, Kevin Alcántara, and Owen Caissie, well, that’s the issue.

The flip side is that the first two of those players are dealing with significant injury setbacks that could jeopardize at least part of 2023. Creating a little security with Happ would mitigate the inherent volatility with prospects while allowing Hoyer to trade from existing depth to address current and future needs. There’s also been talk of interest in Michael Conforto, who could serve as DH or even displace Happ on a deal that presumably would not clog the roster as long.

It’s all a balancing act between cost, risk, and timing, the first two of which Hoyer seems averse to if not outright allergic. Timing hasn’t exactly been a calling card for this front office either, though they do get kudos for sneaking that Marcus Stroman deal in under the lockout deadline last year.

The Benintendi contract doesn’t make either a Happ extension or trade any more or less likely, but it does establish a baseline for any Cubs offer. If I had to guess at the likelihood of a long-term deal for Happ to stay in Chicago, I think I’m leaning 60/40 toward trade. Those odds were flipped in favor of extension just a few weeks ago, but the situation sure feels different now. Ask me again next week and maybe I’ll have a new thought.

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