Pittsburgh Pirates: Best Picks From Each of the First 10 Rounds

The MLB Draft is important to baseball, and especially the Pittsburgh Pirates. These are the best players the Pirates have selected in the first 10 rounds.

The MLB draft is still quickly approaching. We’re just over a month until the Pittsburgh Pirates, and all 29 other MLB teams get to select what they hope are future core pieces for years to come. The draft is vital for a team like the Pirates as they must build from within via player development.

With that being said, the draft has a long history in the Pirates. The amateur draft as we know it today started in 1965. The draft is a long but important process with many rounds. Today, I want to take a look at the best players the Pirates have picked in each of the first ten rounds.

I’m looking at the player’s entire career, not just what they did with the Pittsburgh Pirates if they played with the Pirates at all. Some players had great years with the Pirates but hit their stride once leaving Pittsburgh. So without further ado, let’s get into the tenth round.

Round 9: Tony Watson

One of the best relief pitchers in Pirate history was taken in the ninth round of the 2007 draft. The 278th overall pick, Tony Watson became known for his excellent command throughout his minor league career as a prospect. Though he would be used in a starter and swingman capacity throughout the minors, he’d eventually make the complete transition to the bullpen once he reached the major leagues.

Throughout his first seven years in the major leagues, Watson established himself as one of the best left-handed relievers in the league. His tenure with the Pittsburgh Pirates saw him rack up a total of 433 innings, yielding a 2.68 ERA, 3.59 FIP, and 1.09 WHIP. He only walked 6.9% of batters faced while having a solid 0.85 HR/9 rate and 21.7% strikeout rate.

Watson is arguably the best set-up man in baseball history. He leads all MLB pitchers in holds at 246. He broke this record on June 5th, 2021, with the LA Angels. His 41 holds in 2015 are tied with Joel Peralta in 2013 for the most in a single season. One last notable milestone was his 2014 all-star season, along with Andrew McCutchen and partner-in-crime Mark Melancon.

After leaving the Pittsburgh Pirates, Watson pitched exclusively on the West Coast with the Los Angeles Dodgers, San Francisco Giants, and Los Angeles Angels. He was solid though with him pitching to the tune of a 3.41 ERA, 3.58 FIP, and 1.08 WHIP through his last 195.1 innings of work. Watson recently announced his retirement earlier this year, which ended a streak of 9 straight seasons where he appeared in 60+ games and had an ERA+ of 100 or greater (excluding the 2020 campaign, though he still had an ERA+ well above 100 at 174). He also ends his career with the most holds in MLB history and a sub-3.00 ERA/136 ERA+.

Round 8: Tim Wakefield

Tim Wakefield was an 8th round pick in the 1988 draft. Wakefield started his career as a light-hitting utility infielder before making his transition to the mound. Wakefield used his knuckleball to carve out a nineteen-year, 200-win career. However, the start of his career was a bit rocky, to say the least.

In Wakefield’s rookie season with the Pirates, the right-hander put up a 2.15 ERA, 3.27 FIP, and 1.21 WHIP through 92 innings during the 1992 season. He finished third in National League Rookie of the Year voting behind Eric Karros and Moises Alou. But after heavily struggling in 1993 and then missing 1994 due to injury, things weren’t looking so good for the right-hander.

The Boston Red Sox would then take a chance on him, where he would spend the next 19 years of his career and where he tossed 3006 of his 3226.1 innings. Overall, Wakefield put up a 4.41 ERA, 4.72 FIP, and 1.35 WHIP. Like most knuckleball pitchers, he didn’t have the best peripherals. Wakefield had just a 1.2 HR/9 rate, 15.5% strikeout rate, and 8.6% walk rate. But overall, he was an above-average run preventer, having a 105 ERA+.

Along with 200 career wins, Wakefield also finished third place in Cy Young voting in 1995 and won two World Series. The first was in 2004 and the second was in 2007. He made his first all-star game at 42-years-old in 2009, alongside Jonathan Papelbon, Kevin Youkilis, and Dustin Pedroia, who represented the Boston Red Sox during that year’s Mid-Summer Classic.

Round 7: Willie Randolph

The Pittsburgh Pirates drafted Willie Randolph as a shortstop in the seventh round of the 1972 draft. Randolph quickly progressed through the minor leagues, and by his age-20 season, he was in the Major Leagues. Randolph only appeared in 30 games with the Pirates in 1975 but was dealt the following offseason in a trade the Pirates probably regretted.

The Pittsburgh Pirates dealt Randolph to the New York Yankees, alongside the notorious Dock Ellis, and 1974 All-Star starting pitcher Ken Brett in exchange for Doc Medich from the New York Yankees. Unfortunately for the Pirates, Randolph became one of the best players in Yankee history.

Randolph would spend the next 13 seasons in pinstripes, batting .275/.374/.357 with a .337 wOBA and 110 wRC+. Randolph was an on-base machine who swiped over 250 bags with the Yankees. He was also a great fielder who racked up over 100 total zone runs at the keystone. His 51.4 fWAR in a Yankee uniform is the highest among all NYY second basemen, just beating out Tony Lazzeri, who had a career 48.4 fWAR with the Yankees.

At the end of his career, he spent a few years with the Los Angeles Dodgers and then bounced around in Oakland and Milwaukee. He ended his career in New York, but not in a Yankees uniform. Instead, his last games were spent with their cross-town rivals, the New York Mets.

Randolph is arguably a Hall Of Fame second baseman. He has a 65.9 bWAR, higher than Craig Biggio and on par with Roberto Alomar and Ryne Sandberg. He’s also the 6th best defensive 2B in terms of dWAR (20.2) and beats out 11 other Hall Of Fame keystone defenders in terms of bWAR. His career +115 total zone runs at 2B is the third-best in MLB history, trailing just Pirates’ legend Bill Mazeroski and eight-time Gold Glover Frank White. It’s truly a shame he fell off the ballot after just one year.

Round 6: Ed Whitson

In 1974, the Pittsburgh Pirates picked Ed Whitson in the sixth-round of the MLB draft. The right-hander made his way up the Pirates’ minor league organizations but didn’t play all that much in a Pirate uniform. He was used as a swing-man for the Pirates, appearing in 67 games, including nine starts across two-and-a-half seasons. Whitson provided a 3.73 ERA, 3.93 FIP, and 1.439 WHIP through 147.1 innings.

In late June 1979, the Pirates dealt Winston to the San Francisco Giants with Fred Breining and Al Holland for a three-player package. Although that package included Bill Madlock, Whitson caught his stride after being given a chance to start games regularly.

From 1980 through the end of his career in 1991, Winston established himself as a rock-solid starting pitcher. He would go on to pitch to the tune of a 3.79 ERA, 3.84 FIP, and 1.30 WHIP. Although Whitson didn’t excel in anything in particular, given his 0.9 HR/9 rate, poor 13.1% K-rate, and 6.9% walk rate, he put up solid results everywhere he went.

Whitson would pitch for the Giants, Cleveland, San Diego Padres, and New York Yankees. He retired after his age-36 campaign. He may never have been a top of the rotation arm, but he was a reliable arm everywhere he pitched.

Round 5: Dave Cash

The Pittsburgh Pirates selected shortstop Dave Cash in the fifth round of the 1966 MLB Draft. Although Cash was selected as a shortstop, he’d eventually slide over to the keystone, where he remained most of his career. Cash didn’t spend much time in Pittsburgh. He only had 1767 plate appearances across five different seasons. He was about a league-average hitter, posting a .285/.338/.365 line, .321 wOBA, and 101 wRC+. However, he did display good defense with +19 total zone runs. Plus, he has the designation of being part of baseball’s first-ever all-minority line-up.

He manned the hot corner during that day, which was just one of 41 times he’d ever appear at the position. He went 1-for-3 on the day, drawing a walk and striking out once. He was part of MLB and world history, even if he wasn’t the biggest name on the roster then.

Though after 1973, and after turning in the worst offensive numbers he posted in his career so far, the Pittsburgh Pirates dealt Cash to the Philadelphia Phillies for pitcher Ken Brett, who was brought up earlier. Cash really hit his stride in Philly. He put up similar hitting numbers, batting .296/.348/.371, leading to a .332 wOBA and 101 wRC+. However, he finally got to show off what he could do with the glove over a full season. Cash racked up +21 total zone runs in just three seasons. Brett made the all-star game every season he was with Philly.

After 1976, Cash signed with the Montreal Expos, where he posted a well below-average .277/.322/.355 line, .306 wOBA, and 88 wRC+. Even worse was his defense started to trend in the wrong direction. After the 1979 season, the Expos dealt Cash to the San Diego Padres for Bill Almon and Dan Briggs. Cash would spend his 1980 season as the Friars’ primary second baseman but was released before the start of the 1981 campaign.

Round 4: Jared Hughes

The Pittsburgh Pirates built a monster bullpen in the early-2010’s, which included the aforementioned Tony Watson. But another guy who played a massive role in those early-2010 Sharktank bullpens was right-hander Jared Hughes. The right-hander was their fourth-round selection in 2006. He started his pro career as a starting pitcher but found massive amounts of success when he got to the majors and was put in the bullpen.

Hughes kicked his career off with five terrific seasons with the Bucs. From 2012, his first full season in the majors, up through 2016, Hughes pitched to the tune of a 2.78 ERA, 4.11 FIP, and 1.28 WHIP. Hughes was a ground ball specialist, having a 60.8% ground ball rate throughout these five campaigns. He was just one of 14 other relievers to have a 60%+ ground ball rate throughout 2012-2016.

After the Pirates released Hughes in Spring Training 2017, he would go on to have two more quality seasons with their division rivals. He spent the next two seasons with the Milwaukee Brewers and Cincinnati Reds, posting a 2.41 ERA, 3.56 FIP, and 1.12 WHIP. Hughes kept up his signature groundball approach, posting a 64% GB rate between these two seasons.

But 2019 would be the start of the end of Hughes. He still managed a solid 4.04 ERA with the Reds and Philadelphia Phillies (whom he was selected off waivers by mid-season) but saw his HR/9 balloon to 1.6. Hughes spent the 2020 season with the New York Mets, where his ERA skyrocketed to 4.84, and his walk rate jumped to 12.8%.

Hughes would announce his retirement in February 2021. Hughes was never a top prospect in the Pirate system. He was a pretty unassuming fourth-round selection, but he lasted ten years in the Major Leagues while having a sub-3.00 ERA.

Round 3: Richie Zisk

Richie Zisk was quite the underrated hitter during his time in Pittsburgh. Zisk was the Pittsburgh Pirates third-round pick in 1967 and established himself as a quality player a few years later in 1973. From his rookie campaign in 1973 through his last season with the Bucs in ‘196, Zisk batted .302/.367/.481, .382 wOBA, and 139 wRC+.

Zisk was traded during the 1976-1977 offseason to the Chicago White Sox for Terry Foster and, the big piece of the trade, Rich Gossage. Zisk arguably had the best year of his career with the Sox, batting .296/.355/.514, blasting 30 home runs, all while posting a .374 wOBA and 131 wRC+. But after the season, he was a free agent and signed with the Texas Rangers.

Zisk split his last six Major League seasons with the Rangers and with the Seattle Mariners. However, he just kept hitting. Zisk’s final six campaigns saw him bat .277/.343/.447 with a .352 wOBA and 118 wRC+. Later in his career, Zisk eventually moved out of the outfield and into the designated hitter role.

Zisk was consistently a good batter. He had a ten-year streak of posting a wRC+ of at least 105. That lasted from his rookie season up until the next to last season of his career. Zisk ended up with a very good career that often gets overlooked.

Round 2: John Candelaria

John “The Candy Man” Candelaria was the Pittsburgh Pirates second-round pick in 1972. Candelaria established himself as one of the Pirates better starters in their franchise’s history through the first eleven-and-a-half years of his MLB career. The Candy Man pitched 1873 innings with the Pirates, putting up a quality 3.17 ERA, 3.40 FIP, and 1.17 WHIP.

Candelaria had some hardware from his time in Pittsburgh. In 1977, he made his one and only career all-star game, finished fifth in Cy Young voting and led the league in ERA and BB/9. He also won a ring in 1979, playing a significant role for the “We Are Family” Pirates.

The Pirates traded Candelaria to the California Angels in August of 1985 for Mike Brown, Bob Kipper, and Pat Clemens. Candelaria would then become a journeyman southpaw, pitching for the Angles, both New York teams, the Expos, Minnesota Twins, Toronto Blue Jays, and then the Los Angeles Dodgers. Although he was still a solid pitcher, having a 4.02 ERA/3.58 FIP, he never reached the peak he did during his time with the Pirates.

The Pirates decided to give the Candy Man one last ride into the sunset in 1993, 21 seasons after they drafted him. He only pitched in 19.2 innings, all out of the bullpen, and surrendered 18 earned runs, but he ended his career where it started, which is always nice to see.

Round 1: Barry Bonds

Love him, hate him, there is zero doubt that Barry Bonds was a monster at baseball. The Pirates used the sixth overall pick in the 1985 draft to select outfielder Barry Lamar Bonds, son of Bobby Bonds, cousin of Reggie Jackson, and godson of Willie Mays. If the bloodline didn’t set him up for greatness already, what he would eventually do to baseballs would.

Bonds really didn’t start to hit his stride until the last three seasons in his Pirates career. That’s not to say he didn’t do well in his first four seasons, but ‘90-’92 were absolutely dominant. Barry hit .301/.424/.566 with a .424 wOBA, and 172 wRC+. He was a speed demon with Gold Glove defense and 30+ home run power. He won the Silver Slugger and Gold Glove for left fielders in all three seasons and won the MVP in two of the three campaigns. Heck, he really should’ve won it in ‘91 but didn’t for some reason.

We know what Bonds did in San Francisco, but can we just take a minute to awe in amazement in what he did in the early-2000’s? From 2001 through 2004, Bonds was undoubtedly, and far and away, the best hitter baseball had ever seen. Bonds hit .349/.559/.809 with a .531 wOBA, and 232 wRC+. The difference between a league-average wRC+ and Bonds’ wRC+ in these four seasons is about the same difference between Mike Trout’s career wRC+ and Adam Wainwright’s career wRC+. He drew 284 intentional walks. If you took Juan Soto’s and Joey Gallo’s walk totals from last season, you’d still be 28 walks short.

Bonds is the all-time home run leader. Everyone knows that. He’s also the all-time leader in intentional walks. He has more career intentional base-on-balls than Robinson Cano, Jim Rice, Hanley Ramirez, and even Roberto Clemente have of all walks. His 120 intentional walks in 2004 would have been the second-highest walk total in 2021.

Bond was still among baseball’s best hitters at age age-42 in 2007, his last season in the bigs. He batted .276/.480/.565, posting a .428 wOBA and 157 wRC+. Bonds ranked sixth in wRC+, third in OPS, and seventh in wOBA in his forties. It’s one of the best final seasons put up by any player of all time. He was still hitting at an MVP-caliber, over the age of 40. Most players are super lucky to even be playing when they’re 42-years-old, much less putting up top of the line numbers.

His time in San Francisco made him a baseball legend for all the right and wrong reasons. From 1993 through his last season in 2007, Bonds batted .312/.477/.666. He walked over twice as often as he struck out, with a 23.3% walk rate and 11.4% strikeout rate. He hit more home runs in these 14 campaigns than Mel Ott, Eddie Murray, and Harmon Killebrew did in their 20+ year careers. At the end of the day, he earned a .463 wOBA and 187 wRC+.

I get the steroid argument for these four seasons, but unless Bonds got ahold of some of Captain America’s super-soldier serum, there is no substance or mixture of substances on this plane that makes a player 132% better than the league average. Other notorious steroid users like Alex Rodriguez’s, Mark McGwire’s, Sammy Sosa’s, and Manny Ramirez’s peaks don’t come in the same zip code as Bonds’ peak. Bonds’ best single-season high wRC+ of 244 set in 2003 is 69% better than A-Rod’s, 39% better than McGwire’s, 58% better than Sosa’s, and 62% better than Ramirez’s peak wRC+ marks. Bonds had some off-field issues too, but there is no doubt he was baseball’s best hitter. Bonds had an insane career in Major League Baseball, for better or for worse.