Brian Cashman and New York Yankees playing with prospect fire, could they get burned?

New York Yankees, Yankees, Brian Cashman

The New York Yankees made their first move of the offseason a couple of nights ago. New York traded Gio Urshela and Gary Sanchez for Josh Donaldson, Isiah Kiner-Filefa, and Ben Rortfedt from the Twins.

It was a little bit of a head-scratching move, but it makes some sense. The Yankees were ready to move on from Gary Sanchez and they needed a shortstop. In Josh Donaldson, they feel like they upgraded at third and upgrading across the board was worth taking on the Donaldson salary.

Yesterday, we saw one of the Yanks biggest offseason targets come off the board. From the moment the offseason began, there was chatter that the Yankees really wanted to make a trade with Oakland for superstar first baseman, Matt Olson.



However, the prospect haul would have to be big and Cashman seemed resistant. Well, the Atlanta Braves were willing to do it and they secured the start lefty. Now, the Yankees are still trying to figure out the first base position.

They are in on Freddie Freeman. However, most believe it’s going to be a steep hill to climb to get him. A reunion with Anthony Rizzo could be in the cards, but there’s something that’s struck me in the last couple of days about the Yankees approach this offseason.

Yankees Prospects and Holding on Too Long

A few years ago, Gary Sanchez could’ve been the centerpiece of a trade that brought a legit star to the Yankees. Clint Frazier, Chance Adams, and Miguel Andjuar were requested by the Pirates a few years ago for Gerrit Cole.

Deivi Garcia and Estavan Florial were asked about in trades for proven MLB starting pitchers. Gleyber Torres was asked about in many trades that could’ve brought stars back to the Yankees that could’ve drastically helped this club potentially win a World Series.

Brian Cashman turned down major trades over and over again to hold onto these prospects out of the fear of missing out. In the last few years, there’s really only been one prospect Cashman has held onto that’s turned out to be a star and that’s Aaron Judge.

Remember Greg Bird? Look, I absolutely love the fact that Brian Cashman truly believes in his guys. However, he has really developed a horrible habit of holding onto guys until they virtually have no value at all.

You will not find a bigger fan of Anthony Volpe than me. I also love Oswald Peraza and Jasson Dominguez. They all are sensational prospects. However, all three of them are far from guarantees and Yankees fans have to hope they pan out.

The Prospect Problem and Hopium

Let me ask you, if you were told that Jasson Dominguez and Oswald Peraza were traded for Matt Olson, but the Yankees won a World Series next year would you do it? I would hope many if not all would say yes.

Cashman has behaved like a GM who is half in and half out. Half of him wants to build for the future while the other half wants to win now. You can’t have it both ways and the Yankees are 13 years removed from a World Series as a result.

If Anthony Volpe turns out to be the next Derek Jeter and Dominguez turns out to be the next Mickey Mantle, Cashman is a genius. However, if they both flame out, Yankees fans will once again be left wondering, what if?

What if Gerrit Cole was traded to New York instead of Houston? What if the Yankees acquired Jose Ramirez or Francisco Lindor a couple of years ago for a package headlined by Gleyber Torres.

Yesterdays trade will be another what if? What if the Yankees had made the prospect package needed to acquire Matt Olson. Time will tell, but it’s a risky game that has burned Cashman more times than not in recent memory. I truly hope he’s right this time.