The second day of Pirates Minor League awards featured the recognition of a big-time slugger, plus their top reliever, baserunner and defender.
More on Murf Gray in a moment. He was an obvious choice for Willie Stargell Slugger of the Year and seemingly has a strong shot at winning Honus Wagner Player of the Year on Thursday.
But Derek Diamond was recognized as the Kent Tekulve Reliever of the Year, Yordany De Los Santos was named the Omar Moreno Baserunner of the Year, and Jesus Castillo was named the Bill Mazeroski Defender of the Year, honors for three deserving players who had strong 2026 seasons.
Castillo, 23, made just nine errors in 288 total chances, which works out to a .969 fielding percentage. He also played seven different positions — everywhere but pitcher and catcher — in 100 games up and down Pittsburgh's Minor League system.
With 506 career chances at second base, Castillo has definitely shined there with a .976 fielding percentage. His performance at first base (428 for 431, .993) has also been really good.
Diamond, 25, went a combined 7-0 with two saves, a 2.48 ERA, 57 strikeouts and a 1.02 WHIP in 37 appearances (two starts) between four stops from the Florida Complex League to Triple-A Indianapolis.
After starting the season on the seven-day injured list, Diamond pitched on a rehab assignment with the FCL Pirates and Low-A Bradenton from May 12-19. He joined Double-A Altoona on May 23, delivering 10 scoreless innings with 13 strikeouts, a .063 batting average against and 0.20 WHIP from May 23-June 7.
Promoted to Indianapolis on June 9, Diamond made his Triple-A debut two days later and wound up going 5-0 with one save, a 3.14 ERA and 39 strikeouts in 29 games (two starts) with Indy.
Since making his professional debut in 2022, Diamond is 25-14 in 100 games (43 starts) totaling 296 2/3 innings. He has a 4.70 ERA and 261 strikeouts during that time.
Gray’s 32 home runs led all Pirates Minor Leaguers and were tied with Chad Hermansen (1999), Jon Benick (2004) and Andrew Lambo (2013) for the fourth-most by any Pirates Minor Leaguer since 1999.
Those above Gray on that list: Brad Eldred (38 in 2004), Mason Martin (35 in 2019) and Craig Wilson (33 in 2000).
Gray, 22, hit a combined .305 with 27 doubles, 97 RBI, 66 walks, .969 OPS and 100 runs scored in 126 games split between Low-A Bradenton, High-A Greensboro and Double-A Altoona.
Gray made his debut April 3 at Dunedin and never looked back. He led the Florida State League in hits (51), RBI (34), slugging (.606), OPS (1.042) and total bases (86) while ranking second in batting (.359) and runs scored (29).
Selected out of Fresno State (CA) University in the Competitive Balance-B round in 2025, reached High-A on May 19 and led the South Atlantic League in total bases (105) and ranked tied for first in home runs (15) during his time with the Grasshoppers.
Gray (MLB Pipeline No. 4) made his Double-A debut on July 17 and ranked third in the Eastern League in on-base percentage (.395), tied for fourth in runs (34), seventh in OPS (.879) and tied for eighth in walks (29) from July 17-Sept. 13.
De Los Santos, who’s ranked No. 14 by MLB Pipeline, led the Pirates’ Minor League system in stolen bases with 45. The 21-year-old also hit .260 with 19 home runs, 68 RBI, a .329 on-base percentage, a .483 slugging percentage, .812 OPS and 79 runs scored in 92 games split between High-A and Low-A Bradenton.
Spending much of the season with the Grasshoppers, De Los Santos ranked second in the South Atlantic League in steals (45), tied for second in doubles (26), sixth in runs scored (77), tied for seventh in extra-base hits (44) and ninth in slugging percentage (.481).
This story will be updated.
Jason Mackey: Jason.Mackey@pirates.com and @JMackey_PGH on X.