Welcome to a special edition of the Friday Four. I got tired of writing about minor league signings and depressing labor negotiations, so this week we’re getting sad in a new way.

Inspired by this Tweet from Brandon Warne, I wanted to look at a few of the worst recent first-rounders for Minnesota. Of course, prospect development is not a linear path. Developing high-quality baseball players is a tricky, inconsistent process that leads to many successes and failures. Some teams are better than others at it, and some players develop better in different systems. Brian Dozier likely doesn’t become the power-hitting leadoff man we all know and love if he comes up in another team’s system. For the sake of this exercise, we are assuming that the prospects develop into the exact same players they are now, regardless of the system.

A few other notes: you can only select players who were chosen below the Twins draft pick. We would love to get the top pick every year, but unfortunately, that’s not how drafts work. Second, I am only looking at other first-rounders, including the compensatory and competitive balance rounds. A player selected in the 18th round was not a viable first-round pick, regardless of how good they became down the line. Alright, let’s get into it.

#4: Alex Wimmers

Photo by Stephen Brashear/Getty Images

Wimmers was selected 21st overall in the 2010 draft and is the epitome of the type of pitchers the old front office loved. A solid, polished, lower velocity starting pitcher who likely wasn’t going to improve much from where he was at the time. Here’s Baseball America’s scouting report on him at the time.

Only a hamstring injury has been able to stop Wimmers this spring, as he won each of his first nine starts for the Buckeyes before missing the first two weekends in May. He also starred in 2009, sharing Big 10 Conference pitcher-of-the-year honors before leading Bourne to its first-ever Cape Cod League championship. Scouts said Wimmers had the most polished arsenal on the Cape, and few pitchers in this draft can match the depth of his repertoire. He has the best changeup in the 2010 draft crop, and one area scout said it’s the best he has ever seen from an amateur. His fastball sits at 90-92 mph and touches 94, and he could add a little more velocity if he builds arm strength by using it more in pro ball. His third pitch is a curveball that he easily throws for strikes. He’s an athletic, 6-foot-2, 195-pounder who holds the record for career batting average (.457) at Cincinnati’s storied Moeller High—the alma mater of Buddy Bell, Ken Griffey Jr. and Barry Larkin.

Wimmers would go on to pitch just 24.2 innings in the big leagues, throwing for a 4.38 ERA, 5.87 FIP, 7.7 strikeouts per 9 IP, and a disastrous 6.9 walks per 9 innings pitched. He was, technically, an above-average player in that time, compiling 0.2 bWAR.

Best Selections

Future National League MVP Christian Yelich was selected just two picks after Wimmers. Though his production has dropped off in later years, missing out on an MVP is obviously not ideal. Noah Syndergaard, Thor himself, was also selected later at pick 38. While he has struggled with his health of late, when he has pitched he has been among the league’s best.

Honorable mentions: Cam Bedrosian (29), Aaron Sanchez (34), Taijuan Walker (43), Nick Castellanos (44)

#3: Kohl Stewart

When Stewart was selected fourth overall in 2013, it began a run of very unsuccessful top picks for the Twins. Although he wasn’t supposed to be a stereotypical Twins pitch-to-contact guy, that’s what he eventually turned into down the line. Baseball Prospectus’ draft profile of Stewart is very complimentary of his potential.

Stewart’s ceiling is that of a No. 2 starter who can log innings. May have four major league quality offerings. Due to big time athleticism and the ability to repeat his delivery, the fastball command profile is outstanding, and will also make allow other pitches to play up. The gap between what the pitcher is now and what he will be is fairly large, but he’s very polished for a teenager. The slider has wipe out potential, and could miss bats at the major league level right now. Showed ability to move the ball around to all quadrants and keep the ball off the barrel.

Does little things well on the mound. 1.15-1.27 times to home plate, and neutralized running game. Often would pause for a beat longer and give multiple looks to base runners. Gold glove caliber fielder, and very aware of game situations. Usually would tag high school arms in Low-A with “high” risk proposition, but athleticism and polish give him a higher probability of reaching ceiling.

He’s still active and could turn things around, but I think that’s fairly unlikely. Stewart has thrown 75.2 big league innings to the tune of a 4.88 ERA, 4.87 FIP, 5.4 K/9 IP, and 3.8 BB/9 IP. Over his career, he compiled 0.1 bWAR.

Best Selections

2013 was a deep draft full of quality players, any of which would be an upgrade over Kohl Stewart, but two in particular stand out. Tim Anderson was selected 17th by the division rival Chicago White Sox. Not only is it a missed pick, it’s one we have to be reminded of 20 times a year. Aaron Judge was also selected later in the first round, going 32nd to the New York Yankees.

Honorable mention: Clint Frazier (5), Hunter Dozier (8), Austin Meadows (9), Dominic Smith (11), Hunter Renfroe (13), JP Crawford (16), Sean Manaea (34), Corey Knebel (39)

#2: Tyler Jay

Photo by Cliff Welch/Icon Sportswire/Corbis/Icon Sportswire via Getty Images

With the 6th pick of the 2015 draft, the Minnesota Twins selected Tyler Jay, a move that was questionable even at the time. Jay was a left-handed reliever that the Twins incorrectly believed they could turn into a starter. Relievers are so rarely taken at the top of the draft, that only five others had been taken with a top-10 pick in the previous 20 years. Here’s MLB.com’s draft profile of Jay.

“Jay now works at 93-95 mph and peaks at 98 mph with his fastball, even when he works on consecutive days. He generates that heat with athleticism and a quick arm rather than an excessive amount of effort in his delivery.

Jay has a deeper repertoire than most relievers. His plus slider is his second-best pitch, and he also has a curveball with power and depth and shows signs of interesting changeup. He has enough pitches and control to lead a pro team to consider trying him as a starter, though he lacks size and could speed to the Majors if he remains a reliever.

Unfortunately, none of that potential ever came to pass. Jay would never make it past Double-A with the Twins, eventually trading him to the Cincinnati Reds for cash, where he was later released in 2020.

Best Selections

Walker Buehler. Do I need to say any more?

Buehler is one of the best pitchers in baseball, full stop. At just 26, he has been a two-time All-Star, a perennial Cy Young balloter, led the Dodgers to a 2020 World Series, and been one of the most consistent starters for his team over that time. For his career, he has a 2.90 ERA, 3.20 FIP, 9.9 K/9 IP, and 2.3 BB/9 IP. That’s the makings of an ace.

Honorable mentions: Andrew Benintendi (7), Ian Happ (9), Mike Soroka (28), Ke’Bryan Hayes (32)

#1: Nick Gordon

Nick Gordon could very well go on to have a perfectly fine MLB career. He is currently on the Twins 40-man roster and could have the inside track to the starting shortstop position if the Twins don’t make any further moves. Despite all that, he unfortunately gets the top spot on my list.

This placement is less about Gordon and more about the other available players.

Photo by David Berding/Getty Images

Best Selections

Aaron Nola, a perennial Cy Young candidate, was selected by the Philadelphia Phillies two picks after him at seven. Trea Turner, a perennial MVP candidate, was selected by the Pittsburgh Pirates at pick 13. Matt Chapman, the best defensive third baseman in baseball and MVP candidate before a down 2021, was the Oakland A’s choice at 25. Any one of those three players would instantly make the Twins leaps and bounds better, but instead we got a slightly overqualified utility man. Don’t get me wrong, I love Nick Gordon and hope he was a wonderful career, but it sure would be nice to have Aaron Nola right about now.

Honorable mentions: Kyle Freeland (8), Michael Conforto (10), Michael Kopech (33), Jack Flaherty (34)