ORLANDO -- Good morning and welcome to Day One of the Winter Meetings, that magical annual moment when half the industry is whispering in hotel hallways, the other half is refreshing their phones every 30 seconds, and absolutely nobody knows what the next four days are going to look like.
And if you thought you had a good read on the outfield market, the Pirates, or the Phillies’ future, well… buckle up. The week is already weird, wild, and wonderfully unpredictable.
Let’s dive in.
Harrison Bader has spent the last four seasons living a nomadic baseball life: six teams, countless flights, and enough midseason address changes to make a real estate agent blush. So now that he’s coming off the best season of his career? He wants something radical. He wants stability.
Ken Rosenthal reports that Bader is seeking a three-year deal, which explains why even outfield-needy teams like the Royals might be priced out. And yet, when you look at what he did in 2025, the ask doesn’t look unreasonable. Between Minnesota and Philadelphia, he hit .277 with a .796 OPS and 17 homers, all career highs. Then he arrived in Philly, hit .305, carried himself like a man straight out of a 1997 Gatorade commercial, and injected life into a clubhouse that needed a jolt.
Dave Dombrowski has already said the Phillies want him back, but Bader’s camp wants to shop.
And, for once, he has leverage, because the outfield market behind him isn’t exactly quiet.
Which brings us to the part no one saw coming: The Pittsburgh Pirates are trying to sign Kyle Schwarber.
Not to a minor-league deal. Not to a one-year flyer. To a four-year contract believed to exceed $100 million.
If you just read that twice, you’re not alone.
They’re still considered longshots — Rosenthal made that clear — but the mere fact they’ve even entered the bidding war tells you everything about this Schwarber market. The Red Sox want him. The Mets want him. The Reds — with their hometown-hero angle — might be the sneaky threat.
And while all of that is happening…
Nick Castellanos remains in Philadelphia the way a suitcase remains in your hallway when you’re halfway through packing: not gone yet, but not really staying either.
The Phillies have tried to trade him for two straight offseasons. They’re trying again now. And everyone — the team, the player, the league — expects a separation before Spring Training. Castellanos went on MLB Hot Stove on Friday offering a Zen-like acceptance of his uncertain future, saying he’s focusing solely on preparing his body for 162 games while the trade talks swirl around him.
He even said he’s open to playing first base. And when players start volunteering to learn new positions, it’s usually because the calls are coming in.
But it won’t be simple.
Ken Rosenthal reports that Bader is seeking a three-year deal, which explains why even outfield-needy teams like the Royals might be priced out. And yet, when you look at what he did in 2025, the ask doesn’t look unreasonable. Between Minnesota and Philadelphia, he hit .277 with a .796 OPS and 17 homers, all career highs. Then he arrived in Philly, hit .305, carried himself like a man straight out of a 1997 Gatorade commercial, and injected life into a clubhouse that needed a jolt.
Dave Dombrowski has already said the Phillies want him back, but Bader’s camp wants to shop.
And, for once, he has leverage, because the outfield market behind him isn’t exactly quiet.
Which brings us to the part no one saw coming: The Pittsburgh Pirates are trying to sign Kyle Schwarber.
Not to a minor-league deal. Not to a one-year flyer. To a four-year contract believed to exceed $100 million.
If you just read that twice, you’re not alone.
They’re still considered longshots — Rosenthal made that clear — but the mere fact they’ve even entered the bidding war tells you everything about this Schwarber market. The Red Sox want him. The Mets want him. The Reds — with their hometown-hero angle — might be the sneaky threat.
And while all of that is happening…
Nick Castellanos remains in Philadelphia the way a suitcase remains in your hallway when you’re halfway through packing: not gone yet, but not really staying either.
The Phillies have tried to trade him for two straight offseasons. They’re trying again now. And everyone — the team, the player, the league — expects a separation before Spring Training. Castellanos went on MLB Hot Stove on Friday offering a Zen-like acceptance of his uncertain future, saying he’s focusing solely on preparing his body for 162 games while the trade talks swirl around him.
He even said he’s open to playing first base. And when players start volunteering to learn new positions, it’s usually because the calls are coming in.
But it won’t be simple.
Castellanos is owed $20 million next year, and with four years of league-average offense on his Philadelphia résumé, the Phillies will almost certainly have to eat salary to make a deal happen. It’s been a turbulent marriage, filled with clutch hits, confounding droughts, dugout tensions, benchings, frustrations, and that unmistakable sense that everyone involved sees the writing on the wall.
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