Can new regime duplicate past draft success?

In a little over a week, Pirates fans will get their first look at general manager Ben Cherington’s approach to drafting, as Major League Baseball’s annual first-year player draft will take place June 10-11.

Cherington has more than 20 years of baseball operations experience, with the vast majority of that coming in the Red Sox organization. Most recently, though, Cherington worked for the Toronto Blue Jays, as he spent three seasons there as vice president of baseball operations and was there for the 2017-19 drafts. The same goes for Pirates assistant general manager Steve Sanders, who served as Toronto’s director of amateur scouting starting in September 2016 until leaving Canada for Pittsburgh in December of last year.

For a baseball fan, it’s always interesting to watch a new regime’s approach to the draft. I remember feeling optimistic when Neal Huntington took over, mostly because he had a good reputation as a talent evaluator during his days in Cleveland. And despite Huntington’s perceived shortcomings, the Pirates’ farm system was highly regarded for a portion of his time in Pittsburgh. Prior to the 2013 season, Pittsburgh was ranked No. 5 among all MLB clubs when it came to its minor league system, and the following year — coming off a 94-win season — the Pirates had moved to No. 1 on the minor league hit parade, with talent evaluators touting the potential of prospects such as Jameson Taillon, Gregory Polanco, Austin Meadows and Reese McGuire. Even as recently as 2017, the Pirates were in the top quarter of farm system rankings.

In the last couple of years, though, the prospects haven’t been as bright. Coming into this season, MLB.com had the Pirates rated No. 15, largely on the strength of three Top 100 prospects: right-handed pitcher Mitch Keller (No. 39), third baseman Ke’Bryan Hayes (No. 41) and shortstop Oneil Cruz (No. 64).

So where did MLB.com rate Cherington’s old club, the Blue Jays? One slot behind the Pirates at No. 16, down a bit from its 2019 midseason rank of No. 10. Baseball America (subscription) was much kinder, ranking Toronto No. 6 heading into this season. That continued an upward trend that started with the No. 24 ranking in 2016 and progressed to No. 20 in 2017, No. 8 in 2018 and No. 3 prior to the start of the 2019 season.

Baseball America, meanwhile, had the Pirates ranked No. 23 going into the 2020 campaign; the rankings for the five previous seasons were No. 7 in 2015, No. 11 in 2016, No. 7 in 2017, No. 16 in 2018 and No. 18 going into the 2019 season. Baseball America has Keller as the No. 52 overall prospect, followed by Hayes at No. 56 and Cruz at No. 57.

Cherington’s first draft in Toronto looks to be a bit of a mixed bag at the top end. Logan Warmoth, a shortstop from North Carolina, was the Cherington-Sanders team’s first No. 1 draft choice in 2017, but he has yet to live up to expectations since turning pro. Baseball America doesn’t have Warmoth ranked among Toronto’s top 30 prospects; the website Prospects1500.com has him ranked No. 33, down from No. 15 the previous year.

In that same draft, though, the Blue Jays made Nate Pearson, a pitcher out of the College of Central Florida, the No. 28 pick overall, and Pearson has blossomed into one of the baseball’s top prospects; he was ranked the No. 8 overall prospect by both MLB.com and Baseball America coming into this season and is tops in the Blue Jays system.

In 2018, Cherington and Sanders went for another shortstop with their first pick, this time tabbing Jordan Groshans, a high school player from Texas. He’s currently the Jays’ No. 2 prospect and is ranked No. 75 among all prospects in baseball.

Last year, Toronto opted for pitching in the first round, selecting Alek Manoah, a 6-foot-6, 260-pound right-hander from West Virginia University. He’s currently ranked as Toronto’s No. 5 prospect by Baseball America and No. 4 by MLB.com.

So, how does one evaluate the Cherington-Sanders team’s ability to draft? One way is to consider total accumulated WAR, but because his Blue Jays drafts are so recent, accumulated WAR would not work. But if you look at the duo’s performance in Boston, that might provide a better barometer. If you’re a Pirate fan, that should be reason for optimism, as MLB.com ranked Boston No. 3 in terms of the best farm system for the decade of the 2010s (2010-19), trailing only top-ranked Atlanta and second-place Houston. The rankings were based on more than just WAR, but it played a significant role. USA Today presented a team-by-team look at baseball’s draft from 1996 through 2018, which nearly mirrors Cherington’s tenure with the Red Sox (1999-2016). In terms of accumulated WAR for drafted and signed players, Boston ranked No. 2 in all of MLB and also tied for second when it came to impact players (10 or more WAR) drafted and signed. None of these rankings, of course, take into consideration international signees, and the Red Sox have had more than their fare share of hits in that regard with players such as Xander Bogaerts, Rafael Devers and Yoan Moncada, the last of whom helped deliver Chris Sale from the White Sox.

There’s no guarantee that Cherington and Sanders will be able to duplicate that type of success in drafting or international signings at 115 Federal Street. But based on their track record, I’m excited to see what their regime does in next week’s draft – shortened though it may be – and the three or four drafts that follow.