Pirates’ top-10 picks more bust than boom


To continue reading, log into your account:

[theme-my-login show_title=0]
Pirates No. 4 overall pick in 2009, Tony Sanchez, breaks his bat during a Spring Training game in 2014. – GETTY

Hope yinz like roller coasters.

June 10, the Pirates will make the No. 7 pick in the 2020 MLB Draft, marking the first selection from new general manager Ben Cherington and associate general manager Steve Sanders in Pittsburgh.

While those two would love to make a splash — and history shows that, at No. 7, they absolutely can — the Pirates' recent history with top-10 picks represents a Kennywood-certified journey filled with loops, corkscrews and freefalls aplenty.

In the past 25 years, the Pirates have made 15 top-10 selections in the MLB Draft, giving us plenty of data to comb through today.

We'll break these picks down, tier by tier, to see what kind of expectations we can set for Cherington and company as they stroll to the (virtual) stage June 10.

Oh, and yeah. Keep your hands and feet inside the ride at all times. This one gets wild.


Gerrit Cole | RHP | No. 1 overall | 2011 MLB Draft 

We'll start with a smooth takeoff. Gerrit Cole led MLB in strikeouts with 326 in 2019. In seven seasons at the big-league level, he's made the All-Star team three times, finishing fourth, fifth and second in the Cy Young voting those seasons. His 20-5 record and 2.50 ERA/0.895 WHIP/2.64 FIP in 2019 was just ridiculous, and he used that performance to cash in on the most lucrative contract ever given to a pitcher, a nine-year, $324 million jackpot, handed out by (who else) the Yankees.

Cole's best work came outside of Pittsburgh, no doubt, but that's not a knock on Cole or the pick. The Pirates had the No. 1 overall pick in 2011 and took one of the best pitchers of the current generation. That's as big a win as you can hope for in the MLB Draft.

Jameson Taillon | RHP | No. 2 overall | 2010 MLB Draft 

In Jameson Taillon, the Pirates not only selected an elite pitcher but a human being with elite grit and resolve. Two Tommy John surgeries (2014, 2019). Testicular cancer (2017). And yet:

Yeah, he's fully planning to come back and to come back strong. That's Taillon. His mental fortitude might be his strongest suit, but his stuff on the mound is top-level, too. In 2018, Taillon posted his best career results, going 14-10 with a 3.20 ERA/1.178 WHIP/3.46 FIP, 179 strikeouts, a shutout and two complete games in 191 innings pitched. All indications pointed to Taillon blossoming into an elite starting pitcher in 2019 and beyond until injuries struck — again. Still, you can't fault the draft pick. The Pirates take another Taillon-level player in 2020, and fans should be ecstatic.


Kris Benson | RHP | No. 1 overall | 1996 MLB Draft 

Count me among those who believe in Kris Benson. The Pirates drafted Benson out of Clemson first overall in 1996, and he immediately justified their decision, winning his first big-league start, a 2-1 victory over the Cubs April 9, 1999. In that game, Benson pitched six innings, posting a 1.50 ERA while striking out three. And the first of those three strikeouts came against Sammy Sosa. Might've heard of him. Not a bad way to start a career.

In all, Benson was effective as a rookie, flashing promise across an 11-14 season that saw him post a 4.07 ERA/1.358 WHIP/4.14 FIP with 139 strikeouts across 196.2 innings pitched. Then, in 2000, he was even better, going 10-12 with a 3.85 ERA/1.342WHIP/4.20 WHIP and 184 strikeouts across 217.2 innings pitched ... then came Tommy John surgery. While he had some success for the Pirates and the Mets after his surgery, things were never the same, and he could never top that 2000 sophomore effort. Injuries — he also underwent rotator cuff surgery later in his career — undoubtedly prevented us from seeing Benson's best at the big-league level. But, with the No. 1 overall pick, it appears the Pirates did take an effective starting pitcher with unexplored upside. That's a win for the pick.

Austin Meadows | OF | No. 9 overall | 2013 MLB Draft

Hey, we had to hit a loop at some point on this ride. Pirates fans probably get a little queasy reading about Austin Meadows, whom the team shipped to the Rays as part of the July 2018 trade to bring Chris Archer to Pittsburgh, so I'll keep this one brief. Meadows is only "flirting with greatness" because his MLB experience is limited to just 197 games in two seasons. He made 165 plate appearances for the Pirates in 2018, slashing .292/.327/.468 with five home runs and 13 RBIs before getting traded ... and then becoming a 33-home-run-hitting All-Star for the Rays in 2019. This, in all likelihood, will become an elite pick. Meadows just needs time to prove it.


Pedro Alvarez | Infielder | No. 2 overall | 2008 MLB Draft 

No, for real. Pedro Alvarez was a decent No. 2 overall pick. In fact, he's probably the fourth most productive player on this list, which is ... OK, yeah, that's kinda sad. But it's true. For a brief moment, from 2012-2014, Alvarez looked the part of a No. 2 overall draft pick, hitting 30 home runs in 2012 before topping that and going for 36 dingers with 100 RBIs in an All-Star and Silver-Slugger 2013 campaign. Alvarez's power was inefficient though, a fact made evident through his .236/.310/.447 career slash line across nine seasons (six with the Pirates, three with the Orioles). Would you like to do better at No. 2 overall? Definitely. But was Alvarez a bust? Nope. Not at all. You'll see what a true bust looks like shortly.

Paul Maholm | LHP | No. 8 overall | 2003 MLB Draft 

Sure, Paul Maholm was never an All-Star. He never struck out more than 140 batters in a season. His ERA never sunk below 3.50 for a full season. But he was solid, playing seven seasons with the Pirates before signing with the Cubs in January of 2012. Across those seven years in Pittsburgh, Maholm went 53-73 with a 4.36 ERA/1.424 WHIP/4.21 FIP across 185 starts. He occasionally flashed brilliance, too, pitching three shutouts and five complete games, but could never quite take that next step toward greatness.

Brad Lincoln | RHP | No. 4 overall | 2006 MLB Draft 

Shocking pick here? Maybe. But I'll explain. Brad Lincoln was a dual-sport athlete (baseball/football) in high school who won the Dick Howser Trophy (national college baseball player of the year) in 2006. He was widely considered one of the best players in the 2006 MLB Draft, and the Pirates snagged him with the No. 4 overall pick.

That's where the good ends.

Oblique strain in 2006. Tommy John surgery in 2007.

Lincoln's career never had a chance, and he bounced around, ending his career with a 9-11 record and a 4.74 ERA/1.394 WHIP/4.62 FIP in 22 starts and 222.1 innings pitched. With the Pirates in just over two seasons, Lincoln went 7-9 with a 4.62 ERA. So on the surface, this looks like a bad pick that never panned out. But considering the injuries, his pedigree and the few flashes he did show, it's more likely Lincoln, like Benson up there, is the product of bad luck. To me, he never had the chance to showcase his full potential, so the pick gets a slight pass from me.


Tony Sanchez | C | No. 4 overall | 2009 MLB Draft 

A catcher at No. 4 overall is always going to perk up some ears. A catcher at No. 4 overall who busts gets people fired. Tony Sanchez enjoyed a historic collegiate career at Boston College, making All-ACC first team in 2009 before becoming the highest draft pick in the school's history. The credentials were there on paper ... but they never panned out — at all — at the MLB level. Sanchez progressed through the minors before officially being recalled to the Pirates in 2013, where he posted decidedly unspectacular results. He appeared in just 51 games and made 155 plate appearances across three big-league seasons with the Pirates before eventually being designated for assignment in January 2016. From there, Sanchez bounced around various minor-league systems and even appeared in one more big-league game for the Braves in 2017, but his career was a wrap. You gotta have more production than this from a No. 4 overall pick.

Daniel Moskos | RHP | No. 4 overall | 2007 MLB Draft 

Career stats: 1-1 record, 2.96 ERA/1.562 WHIP/3.23 FIP, 11 strikeouts, zero starts, six games finishes, 24.1 innings pitched. Daniel Moskos wasn't horrible, but he never showcased anything to stick at the big-league level. At No. 4 overall, you're looking for more than decent relief innings across one summer.

Bryan Bullington | RHP | No. 1 overall | 2002 MLB Draft 

This pick isn't Bryan Bullington's fault. But, my goodness, man. Just listen to then-Pirates-general manager Dave Littlefield on the selection:

"There was quite a bit of discussion on where we were going to go. It wasn't a situation where we were trying to be crafty. It was more a situation that it wasn't a year where it was one player standing above anybody else, and we felt we had to consider a lot of different factors. We feel very comfortable and good about drafting Bullington. Being a college pitcher, he's going to be a little closer than a high school draftee ... I'd anticipate we're looking at him a couple of years away."

Translation: The Pirates played it as safely as possible. With the No. 1 overall pick, they took a guy they knew would sign vs. a guy who could legitimately impact the franchise. Zach Greinke went No. 6. Prince Fielder went No. 7.

Bryan Bullington went No. 1. He pitched parts of two seasons for the Pirates before heading to the Indians in 2008, the Blue Jays in 2009 and the Royals in 2010, never posting any results of note.

John Van Benschoten | RHP | No. 8 overall | 2001 MLB Draft 

This might be my favorite bad pick of the bunch. John Van Benschoten hit 31 home runs as a first baseman for Kent State, leading all of Division I baseball. That earned him Mid-American Conference Player of the Year honors, and that 31-home-run mark stood as a single-season conference record until 2015. But here was Van Benschoten's curse: He also performed well as the team's closer, and the Pirates liked his work on the mound more than they liked his performance at the plate.

So they made him a pitcher.

And he flopped.

In three big-league seasons (2004, 2007, 2008), Van Benschoten started 19 times, posting a 9.20 ERA/2.144 WHIP/6.33 FIP en route to a 2-13 record. Among pitchers with at least 75 innings pitched, Van Benschoten has the highest ERA of all time. That is not ideal.

Bobby Bradley | RHP | No. 8 overall | 1999 MLB Draft 

Like Benson and Lincoln, Bobby Bradley never had a real chance to showcase his stuff in the big leagues. Rated by Baseball America as the No. 20 prospect in baseball before the 2001 season, Bradley came to town with high expectations. Then the injuries began. He required arthroscopic surgery in June of 2001 then Tommy John surgery in October of that same year. Another surgery followed in 2003, and that sealed the deal. He struggled in the minors from there before being released so the Pirates could clear room on their roster for Zach Duke. Bradley is a story of "what might have been," but what separates him from Lincoln and Benson is that he never got to showcase his skills at the MLB level at all.

J.J. Davis | OF | No. 8 overall | 1997 MLB Draft 

Taken out of Baldwin Park High School in Baldwin Park, Calif., the Pirates saw plenty of promise in the 6-foot-4, 250-pound outfielder J.J. Davis. Then ... nope. Davis played just three seasons in Pittsburgh and one final year, in 2005, with the Nationals, posting a career slashline of .179/.248/.217 in 67 games and 117 plate appearances. His OPS+ in 2002? Negative 23. Negative 23. Woof.

Mark Appel | RHP | No. 8 overall | 2012 MLB Draft 

I'm going to just toss this one over to my colleague, Alex StumpfMark Appel was such a bad pick, he caused the Pirates to fundamentally changed the way they drafted players from there forward. Yeah. That happened.


Travis Swaggerty | OF | No. 10 overall | 2018 MLB Draft 

Most recently, the Pirates took Travis Swaggerty with the 10th overall pick of the 2018 MLB Draft, and the early signs here are encouraging. Swaggerty was a New York-Penn League All-Star with the West Virginia Black Bears, then he got promoted and became a Florida State League All-Star with the Bradenton Marauders. In the minors, Swaggerty's slashing .257/.339/.381 with 14 home runs and 60 RBIs in 658 at-bats. He's obviously still adjusting and adapting, but there's reason to believe Swaggerty can become a contributor at the MLB level.


Like all things MLB Draft-related, this is a study guide, not the answer key. You gotta interpret it correctly to maximize its effectiveness. Most notably, the people making the decisions on draft day have changed for the Pirates, from Cam Bonifay in the mid-1990s to Littlefield in the early-to-mid-2000s to Neal Huntington from 2007 - 2019, so a grain or two of salt is required when browsing through these picks.

That said, Cherington is batting .500 (1 for 2) in his top-10 picks with the Red Sox, as broken down by Stumpf. Oddly enough, both of those top-10 picks came at No. 7 overall, exactly where he'll pick for the Pirates June 10. With one bust in Trey Ball and one potential future All-Star in Andrew Benintendi in his pocket at that No. 7 slot, what Cherington does in 2020 will "break the tie," so to speak.

But overall ... what a wasteland looking at these picks, right? The only two elite picks here are Cole and Taillon, taken at No. 1 overall and No. 2 overall, respectively. Meadows will almost definitely enter that conversation as well. That's the kind of talent you expect to get when choosing in the top 10, yet the Pirates connected just two, maybe three times in 15 attempts. Beyond those, you have to start introducing qualifiers and "what ifs" just to make players seem good.

Worst of all, there are more definite busts than anything, with seven total, nearly 50 percent of the picks. That's not an encouraging trend. It is worth noting, too, Jason Kendall was the No. 23 overall pick in 1992, while Neil Walker and Andrew McCutchen went back-to-back at No. 11 in 2004-05. More recently, the Pirates took Cole Tucker at No. 24 and Kevin Newman at No. 19 in 2014-15, showing they can connect in the first round.

They just tend to whiff when the stakes are the highest.

Now, it's up to Cherington to reverse course and set a new standard on Federal Street.

To continue reading, log into your account: