How Drafting Michael Cuddyer in 1997 Turned into Two Current Twins

Baseball trade trees are fun. I’ve previously outlined two of the biggest in Twins history, one positive (A.J. Pierzynski) and one negative (Delmon Young). One transaction can set off a chain reaction that lasts decades. This isn’t a complete trade tree, but it is a continuous line that links Michael Cuddyer to Austin Martin and Simeon Woods Richardson.

Cuddyer was drafted ninth overall in 1997 out of a Virginia high school. He was listed as a pitcher and shortstop. It took a while for the Twins to pony up enough money to convince him not to go to Florida State, as he eventually received the sixth-largest signing bonus in the draft at $1.8 million.

Cuddyer consistently ranked in Baseball America’s top 50 prospects, but his major league career did not start smoothly, as he bounced back and forth between the majors and minors from 2001 to 2003, between the ages of 22 and 24. He bounced around the diamond as well, playing five different positions in his first five years.

Finally, he hit his stride in 2006 as a 27-year-old, and he put together six seasons as a solid MLB regular, mostly playing first base and right field, with a 115 OPS+ and an All-Star nod to his name. In 2008, he signed a four-year extension that the Twins. That certainly paid off, and he hit free agency as a 32-year-old ahead of 2011.

Now, this is where the tree would end, if it weren’t for free agent compensation. That year, Cuddyer was a "Type A" free agent, and after he turned down arbitration with the Twins, they were entitled to an additional draft pick. Cuddyer signed a contract with the Rockies, and the Twins were awarded the 32nd pick in the 2012 draft for their troubles.

That 32nd pick? They turned it into Jose Berrios.

Berrios was a high school pitcher out of Puerto Rico and signed for $1.6 million. He was a Top 100 prospect from 2014 to 2016, when he made his messy, messy MLB debut. Across 14 starts in 2016 as a 22-year-old, he had an ERA that started with an eight, but he blossomed into one of the most dependable starters in baseball over the next five seasons in Minnesota.

Unlike with Cuddyer, the Twins had little interest in extending Berrios—at least for the price he wanted. At the trade deadline during the trainwreck 2021 season, the Twins elected to flip Berrios to Toronto for two highly touted prospects. Berrios almost immediately signed a seven-year extension with the Blue Jays.

In return, the Twins received infielder Austin Martin and pitcher Simeon Woods Richardson. Baseball America immediately slotted Martin in as the team’s top prospect and the 19th-best prospect in baseball. Woods Richardson was a borderline Top 100 prospect and was ranked sixth in the system.

Both Martin and Woods Richardson saw their stocks drop over the next few years, but both got their first extended runs in 2024. Martin had a poor showing, raising even more questions about his long-term outlook, but Woods Richardson emerged as a quality backend starter with roughly equivalent performance to Berrios, now 30, in Toronto.

Woods Richardson made the team out of spring training in 2025 but had a rockier start to his season than most had hoped. However, by the end of the season, he’d turned in a solid overall showing in 22 starts.

Martin did not make the team out of spring training and spent considerable time injured at Triple-A St. Paul. However, he may have salvaged his Twins career by being the only hitter to give a quality showing after the team’s historic trade deadline selloff.

Now, both Woods Richardson and Martin are projected to make the Opening Day lineup as a backend starter and a fourth outfielder. Although many expected more from them to this point in their careers, both appear to be useful assets on a team that is trying to get back on track.

If you’re a WAR person, by Baseball Reference’s count, Cuddyer was worth 12.8 rWAR for the Twins. Berrios accumulated 10.0, and Woods Richardson is at 4.0 thus far. Martin accumulated 0.7 in 50 2025 games, but he’s 0.3 wins below replacement for his career. That’s a total of 26.1 rWAR from this string, though, and it could continue to grow. Who knows, Woods Richardson might be traded to create room in the rotation and add another branch onto this tree.

And for the real sickos out there, there might even be another layer to this chain reaction, if you squint and use your imagination, though it is a sad one.

Kirby Puckett was forced into an early retirement before the 1996 season due to glaucoma. The Twins went 78-84 in his absence, tying the Athletics for the American League’s fifth-worst record. At that time, the draft order alternated between leagues, and in 1997, the American League drafted first, meaning that the Twins would either have the ninth or 11th pick.

The Twins had a worse record in 1995 than the Athletics, so they were awarded the higher pick. With just one more win, they would have picked 11th.

Now, I’m no soothsayer, and I can’t create an alternative history. But had Puckett not been forced into retirement, and the Twins instead had their aging superstar patrolling right field (instead of Matt Lawton, Roberto Kelly, Denny Hocking, and Ron Coomer), it’s not difficult to imagine the team winning at least one more game.

And had they won one more game, picking 11th instead of ninth, it’s possible that Cuddyer could have gone to the Athletics or the Cubs (Oakland’s pick that year was Chris Enochs, a college pitcher who never made the majors).

Obviously, this is desperately searching for an extra layer that can only be tenuously held together, but hey. I find it interesting. Either way, the Cuddyer-to-Berrios-to-Martin-and-Woods Richardson thread is a fun one to pull.