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Cubs Prospect Perspective: Donnie Dewees

He’s an older guy, traded away and reacquired. One thing for sure: He’s easy to root for.

Photo by Dylan Heuer/Iowa Cubs

Today’s prospect perspective is on Donnie Dewees. While I’ll talk about him a bit, most of this article is a pure distraction from talking about him. I have a story I want to tell, and I’m going to tell it. If you nod off a bit in the middle, as I do during an Agatha Christie audiobook on occasion, then so be it. Nonetheless, Dewees has a fun backstory, and I’ll get to it, eventually.

Donnie Dewees, outfield

Born September 29, 1993, Inverness, Florida.
Drafted in 2015 (2nd Round, Cubs) from University of North Florida
Acquired in a trade with the Royals — after being traded to KC for Alec Mills

In 2019, my older brother and I went to a baseball game in Peoria. The Cubs affiliate wasn’t playing, but I wanted to see a game with my older brother. As I’ve mentioned a few times, he had been a very good White Sox fan until the 1994 strike. After that, he’d be a good person to talk Bears, Bulls, or Blackhawks, but baseball was dead to him. He got that I did the baseball thing, but he didn’t really “get” it. “Who are we cheering for?” Who are the good players?” “Are we cheering against someone?”

As well as getting ceremonial shot glasses that we thought could be used and washed in a machine (alas, no), he saw who I have become. We were cheering for whoever did something well, assessing the umpire’s strike zone, and not even worrying about the other stuff. I even got to meet Jesse Goldberg-Strassler, the fantastic announcer for Lansing. (As I remember, Alejandro Kirk hit a few frozen ropes that night.)

I don’t think my brother agrees with my time-management skills regarding baseball, but he finally gets what I do. When you overlay four (or six, or eight, or nine) Cubs pipeline games over the MLB club, he understands why I do what I do. Even if he considers it a bit of a rabbit hole. He got to see what I do.

A few years earlier, my dad and I saw a game at Quad Cities, and Dewees was in the outfield for the visitors. For whatever reason, I was down the right-field line with my traditional three-ring binder. As best as I can remember, Dewees asked me if I wanted his autograph. (I wasn’t really autograph hunting, but yeah, sure. Why not? Within a few hours, as my older brother got to see what I do a few years later, I got to see what Dewees does. Run like a gazelle. For a triple up the gap.

When Dewees was in the draft process, the draft date was pushed back a few days. This made Dewees draft-eligible, and many teams hadn’t scouted him heavily because of it. (Since then, teams have gotten better at scouting future year players. The portable iPad device is a scout’s friend, and data storage space is cheaper than it had been.) The Cubs traded Dewees to Kansas City in one of the quicker DFA Wire Portal transactions ever. Designated, then traded, in the same day, and the DFA wasn’t announced until the afternoon. The Cubs received Alec Mills for Dewees, and got Dewees back in about a year in a trade for Stephen Ridings, who debuted for the Yankees in 2021. (Ridings was released by the Royals during the COVID summer.)

I get the impression Dewees would make a fantastic coach. He has good speed, and utilizes it well. He’s also a very good outfielder, despite an arm of middling strength. Nonetheless, he’s also willing to chip in as a reliever whenever needed, and has a Triple-A save despite a 15.00 ERA. It would be fantastic if Dewees would get a late-season look at some point. While I doubt he’d have a lengthy career, it would be cool for me. And all the fans of Cubs affiliates who have cheered him along the way. Guys like Dewees are easy to root for, whether they’re considered “valid major league talents” or not. For some of us, that’s not a prerequisite.

The kid wats that ball.


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