A Lose-Lose Situation

The Oakland A's trades of their star players this off season and last off season have left the team's fans either livid, resigned, naively hopeful, or all three. Armchair analysts have criticized the team for the minor league players that the A's have received in return, suggesting countless other combinations of prospects—even though they have never seen these young players in person. Most A's fans are lamenting that the Matt Chapman trade of last off season is painfully like the Josh Donaldson trade.

But the Boston Red Sox's recent release of Jeter Downs has made the case with an exclamation mark that most of the time when a team trades away a star player who is on the verge of free agency for several prospects the trade does not work out for that team. There are three basic reasons for this.

First, the team trading the star play has little leverage. Every other team in the league knows that if you do not accept a trade, you will lose the player to free agency and receive nothing in return. So, as we learned in pre-school: you get what you get, and you don't get upset.

Next, a bird in the hand is worth more than two in the bush. The star player you have will almost always have a better career than the prospects you receive in return. Every fan wants their team to pull off the next Doyle Alexander for John Smoltz trade, but those trades are the exception. To state the obvious, only a small fraction of minor league players have meaningful careers in the major leagues, let alone become hall of fame players. Most prospects do not have long, productive major league careers. There is a long list of prospects labeled can't miss by experienced talent evaluators who missed badly.

Last, for obvious reasons, teams often feel reluctant to trade away prospects at the tippy top of their prospect list. As such, they tend to offer the team trading away the star play their next best prospect or worse. Thus, the team losing the star player ends up receiving the equivalent of what's behind door number three.

So, teams trading away a star player on the verge of free agency are in a lose-lose situation. If they let the player walk away and sign a large contract elsewhere, fans will criticize the team for not salvaging some value out of the player by trading him before free agency. But if they trade the star player before he reaches free agency, the chances are nearly certain that the prospects they receive will flop and fans will criticize the team for its poor player evaluation.

To prove my point, here is a list of recent trades of star players for minor league talent. And, as an A's fan, to make my point less painful, I am not going to include the trades of Josh Donaldson or Sonny Gray. All references to WAR are from the website baseball-reference. Also, all WAR is from the point of the trade to the present, regardless of what teams the players went on to play for. I understand that some of the prospects have not accumulated a lot of WAR because they have mostly played in the minor leagues. I also concede from the outset that I am cherry picking trades to make an obvious point. Everyone reading this article can point to a star-for-prospects trade they love to hate or one that worked out, but the list below still serves as an uncomfortable reminder that even seasoned scouts often misjudge talented prospects.

1. Rangers trade Yu Darvish to the Dodgers for Willie Calhoun, A. J. Alexy, and Brendon Davis -€” July 31, 2017

Even with injuries, Darvish has racked up 12.1 WAR since the Rangers traded him. The trio the Rangers received from the Dodgers has netted -2.1 WAR. Ouch!

2. Tigers trade P Justin Verlander and OF Juan Ramirez to Astros for OF Daz Cameron, P Franklin Perez, and C Jake Rogers -€” August 31, 2017.

Verlander accumulated 21.6 WAR for Houston, even with Tommy John surgery. Cameron, Perez, and Rogers? So far, they have combined for .6 WAR. Double ouch!

3. Marlins trade OF Christian Yelich to Brewers for OF Lewis Brinson, OF Monte Harrison, IF Isan Díaz and P Jordan Yamamoto -€” January 25, 2018

Even with his injuries, Yelich has earned 18.7 WAR for the Brewers. The quartet that the Marlins received has accumulated -6.2 WAR so far. Oy vey!

4. Orioles trade Manny Machado to the Dodger for Yusniel Diaz, Dean Kremer, Zach Pop, Rylan Bannon, and Breyvic Valera -€” July 18, 2018.

In half a season with the Dodger, Machado earned 2.5 WAR—which is almost the same that the quintet that the Orioles received has earned so far at 2.6 WAR. In his career with the Dodgers and the Padres, Machado has accumulated 20.1 WAR. Ugh!

5. Red Sox trade Mookie Betts, David Price, and cash to the Dodgers for OF Alex Verdugo, SS Jeter Downs, C Connor Wong -€” February 10, 2020

In three seasons with the Dodgers, Betts has earned 14.2 WAR, even though one of those seasons was shorted by the COVID pandemic. The trio the Red Sox received has so far earned 5.1 WAR, with nearly all of it coming from Verdugo.

Obviously, this list is not definitive. But it is enough to painfully remind teams with star players about to leave for free agency that trading away those players is not a sound plan for laying the foundation for the next competitive core of players.

It should also give team officials and fans pause before trading away a player on the verge of free agency. For example, when the A's traded Sean Murphy to the Braves he had three seasons left before he hits free agency. Last year, Murphy earned 3.5 WAR. It is not unreasonable to assume that, given continued health, Murphy could earn 10-15 WAR in the next three seasons. Given the unpredictable record of prospects, is there any reason to assume that the players the A's received in return will accumulate that amount or more? And if not, would the A's have been better to let Murphy play out the three years in Oakland and then walk away?

Undoubtedly there is no substitute for a farm system that consistently drafts and develops the next generation of talent. Clearly that is easier said than done. But it is a message that A's fans hope Oakland's front office understands.