For Pirates, owning the No. 1 pick in MLB Draft has been a boom-or-bust proposition

Picking first overall in the MLB Draft can be a boom-or-bust proposition, one the Pittsburgh Pirates know all too well as they prepare to make the top selection in Sunday’s first round.

The four times the Pirates have owned the No. 1 pick, they have chosen college prospects — one position player and three right-handed pitchers — who have one All-Star appearance between them with Pittsburgh.

Where Gerrit Cole was as advertised, Bryan Bullington proved to be a monumental mistake. Jeff King and Kris Benson were good players who never became great. None was a franchise savior.

Here’s a look at the Pirates’ first four No. 1 overall picks, how they fared in their major-league careers and some of the prominent players the Pirates passed up in the process:

1986: Jeff King, SS, Arkansas

Hits: King arrived in the majors in 1989 and became the starting third baseman for three consecutive NL East Division champions, allowing Bobby Bonilla to move to right field. King hit 14 home runs with 53 RBIs in 1990 and 14 homers with 65 RBIs in ’92. In eight seasons with the Pirates, he slashed .258/.320/.417. His most productive season was in 1996, when he hit 30 homers with 111 RBIs in his final year with the Pirates before being traded along with Jay Bell to Kansas City for Joe Randa and three pitchers.

Misses: The Pirates passed up a pair of prominent arms to take King. Texas lefty Greg Swindell (123-122, 3.86 ERA in 17 seasons) went No. 2 to Cleveland. Georgia Tech righty Kevin Brown became a six-time All-Star who won 211 games and had a 3.28 ERA in 19 seasons, including a 21-win campaign in ’92. The bigger misses were UNLV third baseman Matt Williams (No. 3), a five-time All-Star and four-time Gold Glove winner who hit 378 career homers, and high school shortstop Gary Sheffield (No. 6), a nine-time All-Star who had 509 homers and 2,689 hits over 22 seasons.

1996: Kris Benson, RHP, Clemson

Hits: After leading Clemson to the College World Series and pitching for Team USA in the Olympics, Benson was highly regarded and signed for a record $2 million bonus. He made his major league debut in 1999, going 11-14 with a 4.07 ERA in 196 2/3 innings over 31 starts. Benson proved to be a workhorse the next year, going 10-12 with a 3.85 ERA in 217 2/3 innings over 32 starts. He missed the 2001 season after undergoing Tommy John surgery and never developed into the dominant starter the Pirates projected. Benson was 43-49 with a 4.26 ERA in five seasons when he was packaged with Jeff Keppinger and traded to the Mets in 2004 for Jose Bautista, Ty Wigginton and Matt Peterson.

Misses: In what proved to be a weak draft, the Pirates passed on San Diego State first baseman Travis Lee, who finished third in NL Rookie of the Year voting in 1998 but never became an All-Star. The best of the bunch was R.A. Dickey, who was selected 18th overall and, after reinventing himself from a conventional pitcher, became the first knuckleballer to win the Cy Young in 2012.

2002: Bryan Bullington, RHP, Ball State

Hits: That Bullington allowed only 25 hits as a Pirate is telling, considering he started only three games in two seasons. Projected as a No. 3 starter by then-GM David Littlefield, Bullington failed to secure a spot in the starting rotation. He was 0-3 with a 5.89 ERA in 18 1/3 innings in six appearances, was demoted to Triple-A Indianapolis and eventually designated for assignment. In five major-league seasons, Bullington was 1-9 with a 5.62 ERA.

Misses: The Pirates passed on prep star B.J. Upton, who went No. 2 to Tampa Bay, and missed on future six-time All-Stars in high school right-hander Zack Greinke (No. 6, Kansas City) and slugger Prince Fielder (No. 7, Milwaukee). Greinke has won a Cy Young, six Gold Gloves and has 216 wins and a 3.38 ERA in 18 seasons. Fielder smashed 319 home runs, including 50 in 2007, and had a 141-RBI season in 2009. Other first-round All-Stars included Joe Saunders, Scott Kazmir, Nick Swisher Cole Hamels — the 2008 World Series MVP — and Matt Cain.

2011: Gerrit Cole, RHP, UCLA

Hits: After signing for an $8 million bonus, Cole made an impressive major-league debut by hitting 99 mph on the radar gun on his first strikeout. He went 19-8 with a 2.60 ERA and recorded 202 strikeouts in 208 innings over 32 starts in 2015, when he was selected an All-Star, but followed that by going 10-7 with a 3.88 ERA in 21 starts in ‘16. After going 59-42 with a 3.50 ERA in five seasons, the Pirates traded Cole to the Houston Astros for Colin Moran, Joe Musgrove, Michael Feliz and Jason Martin. Cole is 50-17 with a 2.74 ERA since with the Astros and Yankees, who signed him to a nine-year, $324 million contract after he led the AL with 326 strikeouts in 2019.

Misses: The Pirates got the Cole pick right but the trade wrong. It was a loaded draft, with future Cy Young winner Trevor Bauer (No. 3), All-Star third baseman Anthony Rendon (No. 6), Gold Glove shortstops Francisco Lindor (No. 8) and Javier Baez (No. 9), World Series MVP George Springer (No. 11), as well as the late Jose Fernandez. Rendon, Springer and Baez starred for World Series champions, and Bauer and Lindor were on the Indians’ 2016 AL champions and Cole played for the Astros’ runners-up in 2019.