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When is the right time to sell?

First movers may pay a premium to acquire top talent, but could end up avoiding a highly competitive market.

Houston Astros v Oakland Athletics Photo by Ezra Shaw/Getty Images

The New York Yankees are a really good baseball team. Entering play on Wednesday, they had a 98.3-percent chance of making the playoffs. They sport as dominant a starting rotation as I’ve ever seen on a Yankee team. Oh, and they have a 5.5-game lead in the AL East at the time I’m writing this.

That’s not to mean there aren’t holes in this roster — the massive steps back taken by Aaron Hicks and Joey Gallo have highlighted a possible need for outfield assistance, and injuries to the bullpen have left it a little thin. The Yankees have already made a move to pick up veteran Matt Carpenter to provide infield depth while Josh Donaldson and Giancarlo Stanton are on the shelf.

Between all that and the cushion this hot start has given the Yankees, it’s unlikely that they start to dabble in the trade market for any real impact pieces. They will be buyers closer to August 2nd, but the market just isn’t open right now.

I am, however, much more interested in the other side of the market. Why aren’t the sellers selling?


Look, with all respect to these four clubs, nobody was really expecting much of anything out of them. Oakland already sold off major parts over the winter, the Reds telegraphed that they were uninterested in competing this year, and the Pirates have Bryan Reynolds, the recently-extended Ke’Bryan Hayes, some interesting relief arms with team control, and a couple deck chairs in ball caps filling out the infield. The Cubs might have added Seiya Suzuki in the offseason, but one man alone can’t instantly pull that team out of its rebuild.

So why aren’t any of these ballclubs actively shopping players? They all have pieces who will attract attention at the deadline, and especially when it comes to pitching, the difference between two months of a live arm and four can make the difference for a bubble team. That might not apply to these Yankees, but teams in that 50-60 percent playoff odds — think the Rays, Twins, Angels, and Braves — could really benefit from an extra six weeks of a talented player. Remember, the eventual champion 2000 Yankees didn’t clinch a playoff spot until the season’s final weekend; had they acquired David Justice’s 145-wRC+ bat on July 30th rather than June 30th, their dismal September might have been even more dicey than it already was.

Trading players often functions as an open auction. There may be the odd time when a specific player is targeted, like how the Yankees were seemingly the only team in on Clay Holmes last year, but for the most part, the trade market unfolds exactly how it did around, say, Matt Olson. Everyone knows the trading team is putting the player on the block, and any interested parties can get into the bidding.

I can’t imagine that teams don’t know Oakland’s Frankie Montas or Cincinnati’s Tyler Mahle are available for bidding, but I am curious about the particular market forces at play. Acquiring teams want to give up the smallest prospect package, obviously, but when all buyers concentrate their bidding in a ten-day period, doesn’t that drive up what you’re expected to deal?

This was, apparently, the reason why Brian Cashman didn’t delve too hard into the Olson sweepstakes — too many teams were involved in the bidding, driving prices up. Therefore, I have to wonder about a first mover advantage for teams, where if the Angels felt they needed to shore up their rotation, it would make sense to pursue Montas or Mahle now, rather than wait for other bidders to drive up the prospect return; or at least, the premium you pay for trading early would be no different than the premium you pay in a bidding war. The benefit, of course, is that Tyler Mahle starts six more times for you than Reid Detmers does this season, in a tight division race.

So the acquiring team pays a premium either way, and the trading team benefits. The drawback to dealing so early is that you’re signaling to your fans that you don’t care about the outcome of the 2022 season ... but I think the fans of the Athletics, Reds, and Cubs are sadly all aware of that.

Lastly, it’s possible that teams wait so long because they have other things on their mind. Early-season sample sizes mean that front offices have to delve into what’s real and what’s a factor of two bad weeks. The draft is coming up, prospects are approaching Super Two status; maybe everyone’s just too busy to think about the trade market now. Still, I have to think that there’s some value being left on the table by waiting, and waiting, and waiting, until the real “trade season” starts.