Three Nick Castellanos trades that show how little the Phillies should expect in return

The most important variable in any negotiation is what the other side thinks you are willing to pay. Right now, the other 29 teams in Major League Baseball have every reason to think the Phillies aren’t willing to pay Nick Castellanos anything. That’s a tough starting point for Dave Dombrowski as he tries to find someone interested in trading for the veteran right fielder.

Fact is, Castellanos is due to make $20 million this season, which is at least $18 million more than he could reasonably expect to make if he were a free agent. Even if the Phillies eat most of that money, why would a team trade anything of value for Castellanos rather than signing this year’s version of Mark Canha for a couple of million bucks?

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The only realistic option for the Phillies is to find a team that is looking to shed a similarly overpriced contract. Even then, Dombrowski may have to further incentivize an interested party. That quickly leads to a point where the Phillies are better off simply releasing Castellanos. Or walking a lot of things back before he reports for spring training.

Here are three examples of deals that maybe, kinda, sorta, if you squint could potentially make a fraction of a smidgen of sense for both parties.

Get excited!

This is the baseball equivalent of one of those NBA trades in which a couple of overpriced veterans and 16 second-round draft picks change hands but nobody ends up with more than they started with. You only live once, baby.

Benintendi has been a sunk cost the moment he signed a five-year, $75 million contract in Chicago in 2023. Was it only three years ago that the White Sox were trying? Apparently, it was.

Benintendi hit free agency as the rare hitter still in his prime, having broken into the big leagues at 21 years old on the watch of none other than Dombrowski. He hasn’t come close to the .782 OPS he posted in his first seven seasons in the majors, hitting just .245/.309/.391 in his first three years with the White Sox. He showed a little life in the second half of last season and finished with a .738 OPS that was slightly above league average. But he didn’t show nearly enough life to warrant salaries of $17.1 million this season and $15.1 million in 2027.

Swapping Castellanos for Benintendi would make some sense from an accounting perspective. The Phillies would be taking on an additional $12.2 million in “dead” money over two years. More importantly from a competitive standpoint, they’d be tacking on $15 million in average annual value to next year’s payroll rather than paying Castellanos $20 million up front and then being free and clear.

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But what if the White Sox included $10 million in cash to pay Benintendi’s 2027 salary? That would essentially enable the Phillies to split up Castellanos’ money over two years, saving them $10 million this year while adding $10 million next year. And, hey, maybe Benintendi gives them a little something in the outfield rotation as a Max Kepler replacement. At 31 years old, the chances of that aren’t zero.

What’s in it for the White Sox? Well, they’d save $5 million in cash in 2027 at the expense of an extra $3 million this year. I’m not sure whether this trade makes sense for both sides or makes sense for neither side. But that’s where we’re at.

Truthfully, I’m not sure how much sense this makes for either side. O’Neill signed a three-year, $49.5 million contract last offseason after a big year with the Red Sox (.847 OPS, 31 home runs). He was a major disappointment, posting a .684 OPS and nine home runs in 209 plate appearances in a season marred by injuries.

The argument from the Phillies’ perspective goes like this. They’d essentially be signing O’Neill to a two-year, $13 million deal, given the $20 million they are saving on Castellanos. That’s pretty close to fair market value for O’Neill, who has mostly been a league-average hitter outside of his two spike years (2021 with the Cardinals and 2024 in Boston).

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The Phillies get a right-handed hitter who still might have another big season in him. Even if he doesn’t, maybe he is an adequate enough rotational corner outfielder for two years (O’Neill is heading into his 31-year-old season). They also save $3.5 million on this year’s official payroll.

Is all of that worth $16.5 million less in spending power next offseason? Probably not.

Likewise, what are the Orioles really gaining? Saving $13 million over two years isn’t nothing. But it’s probably not worth sacrificing the chance that O’Neill bounces back.

Freeland, who has spent his entire career with the Rockies, has one year and $16 million left on his deal. That’s a lot to pay a guy who has a 5.07 ERA over the last three seasons. Castellanos has hit well at Coors Field with a .914 career OPS in 88 plate appearances. The Phillies get another piece of rotation depth in the form of a guy who has had some decent years on the road in his career. The Rockies get a guy who at least has chance of regaining some value between now and next year’s trade deadline.