Pittsburgh Pirates: Ben Cherington’s Yearly Report Card

With the 2021 season a few weeks behind us, let’s take a look at Ben Cherington’s past year as general manager of the Pittsburgh Pirates

The Pittsburgh Pirates went into a rebuild on the very last day of the 2019 season when they fired longtime manager Clint Hurdle. That was one of the first major firings the Pirates did throughout the 2019-2020 offseason.

But one of the biggest, and arguably best changes the Pittsburgh Pirates made was firing Neal Huntington and bringing in former Red Sox and Toronto Blue Jays front office personnel Ben Cherington.

Before coming to the Pittsburgh Pirates, Cherington had a strong resume. He was one of the main factors to the Red Sox 2013 and 2018 World Series-winning cores and was also there for the development period of Vlad Guerrero Jr., Cavan Biggio, Bo Bichette, drafted some pretty notable names such as Nate Pearson, Jordan Groshans, and Alek Manoah while acquiring Simeon Woods-Richardson and Anthony Kay for Marcus Stroman.

Cherington did a very good job in his first year as general manager acquiring some good talent for Starling Marte and signing some noteworthy international prospects. But how has his last year gone? I’m mainly looking at what he’s done since the start of the 2020-2021 offseason to now, so anything he did in 2019-2020 and throughout the 2020 season won’t be considered for this.

Acquisitions

The Pittsburgh Pirates made two MLB signings during the 2020-2021 offseason. The more popular of the two was Tyler Anderson. Anderson provided solid results for a 1-year, $2.5 million free agents.

Anderson put up a 4.35 ERA, 4.27 FIP, and 1.20 WHIP. Anderson went at least 5 innings and allowed 3 or fewer earned runs in just 3 of his 18 outings, providing the Bucs with a durable arm every 5th day.

The other MLB signing was fellow pitcher Trevor Cahill, who landed a 1-year, $1.5 million deal. Cahill was expected to fill a similar role to Anderson but ended up injured for most of the campaign. He pitched just 37 innings, allowing 27 earned runs. Though he did have some solid underlying numbers, Cahill never got the chance to show if he could rebound later in the season as he would pitch his last game on June 11th.

Most of the Pirate minor league signings either didn’t play with the major league team or played very little, except for Chasen Shreve who turned out to be a solid minor league signee. He gave the Pirates 56.1 innings, posting a 3.20 ERA, 4.73 FIP, and 1.26 WHIP. He did allow his fair share of walks (11.9% walk rate) and struck out just 19.1% of all batters faced, but he had a workable 1.12 HR/9, and a 77 ERA- isn’t bad for a minor league signed player.

One of Cherington’s wavier claims, Ben Gamel, turned into a solid outfielder. Gamel turned in a .255/.352/.399 line through 383 plate appearances. Although Gamel provided very little power, he got on base at a fair rate with a strong 12.5% walk rate. Gamel provided about 5% better than league average production, posting a 105 wRC+.

Another player I want to bring your attention to is Yoshi Tsutsugo. Originally brought in as a depth player, Tsutsugo quickly made the best of his time in Pittsburgh. He only had 144 plate appearances but put up a strong .268/.347/.535 line, crushed 8 home runs and had a 134 wRC+.

Wilmer Difo was another positive from the low-cost/low-risk signings Cherington made. He had 240 plate appearances, batting .269/.329/.384 with a .312 wOBA, and 95 wRC+. Not terrible numbers for a super-utility guy who played all over the infield and even some outfield. Plus he had a solid 110 wRC+ with RISP and 139 wRC+ as a pinch hitter. While not the greatest signing of all time, Difo gave the Pirates a very reliable bench bat and utility man.

Now granted, some of Cherington’s low-risk acquisitions fell flat. Dustin Fowler only appeared in 18 games and had 46 plate appearances. But he limped to just a .434 OPS. Another low-risk outfield option Cherington took a gamble on was Ka’ai Tom. Tom who was selected by the Oakland Athletics in the 2021 Rule 5 draft, was put on waivers and claimed by the Bucs. Tom had 117 plate appearances and a sub-70 wRC+ (64). Cherington was brought in to fill in the second catcher role. But he provided no value with the bat (38 wRC+) and was a league-average glove behind the dish at best. Anthony Banda, while having a solid ERA, gave up his fair share of walks and home runs.

Grade: C+
Most of Cherington’s pick-ups (waiver claim, free-agent signing, etc.) were low-risk deals. Some worked out, some didn’t.

Draft

How can you look at his most recent draft and not be impressed? Ben Cherington’s 2021 draft was phenomenal by any measure you use. The Pittsburgh Pirates had the first overall selection and Cherington used it to the fullest of his ability and then some. The team selected Henry Davis first overall. While at the time, it was a bit questionable to go under slot with the number one overall pick in the draft, Cherington showed why he picked Davis there.

The Pittsburgh Pirates then selected Anthony Solometo with their second-round selection. Going into the draft, Solometo was arguably the best left-handed prep arm available. With outstanding command and a funky delivery that helps his already good offerings play up, Solometo went for over slot money.

The Pirates got another over-slot deal with their second-round competitive balance pick in Lonnie White Jr. White Jr. is a very high-ceiling high school outfielder. He showed plenty of power throughout his amateur career with good speed and a plus glove out in center. Though he has some swing-and-miss concerns, he didn’t have any major red flags when the Bucs picked him.

But what sealed the deal for this being such a good draft class was the organization’s third-round pick. With the 72nd overall selection, the Pittsburgh Pirates picked up two-way high school star Bubba Chandler.

Arguably the best high school prospect up there with Jordan Lawlar, Marcelo Mayer, and Kahlil Watson, many had Chandler as a top 20-15 selection. After all, he’s a powerful and athletic shortstop with four offerings that project as average or better. But he fell all the way to the Pirates at #72. So how were the Pirates able to sign him? The team did have to go way over slot to sign him, giving him a $3 million bonus even though his slot value was less than $900,000. That was enough to pry him away from his Clemson football commitment, which was the main reason he dropped to the 72nd spot.

But to get four players that were projected to go in the first 50 picks is an outstanding use of the draft. The team also got some other notable names such as Owen Kellington, Jackson Glenn, Mike Jarvis, and even some of their late-round picks have performed well so far in their first taste of professional action.

While Cherington went over their allotted draft money to sign the players they did, it was 100% worth it. The amount of talent they added in just a few days was impressive, which is a major understatement.

Grade: A++
This draft could fuel the fire for many years to come and then some.

Trades

The first major trade Cherington made dating back to the beginning of the 2020-2021 offseason was Josh Bell. Bell was coming off a poor season and had been an extremely inconsistent batter throughout his time with the Pittsburgh Pirates. Not only could he ever find consistency, but he was also one of the worst defensive first basemen in baseball. The Bucs dealt him to the Washington Nationals for two prospects, that being Wil Crowe and Eddy Yean.

Crowe pitched 116.2 innings in the major leagues with the Pirates this year but had a poor 5.48 ERA, 5.67 FIP, and 1.569 WHIP. While the expectations for Crowe as a starting pitcher weren’t high, he could still develop into a back-of-the-rotation arm or swingman type reliever.

Yean spent the season at A-Ball Bradenton where he put up a 5.27 ERA, FIP, and 1.43 WHIP. While he did have a solid 23.3% strikeout rate and 1.08 HR/9, walks were his main issue (13.2%). Though he did have a strong 52.6% ground ball rate and displayed some solid stuff at Bradenton which gives hopes that he can rebound in 2022.

Yean will be 20 for about half of the 2022 season, so he still has time to figure things out. Bell turned things around in DC having a quality 118 wRC+ and 27 home runs. But he continued to display below-average defense at first base and only had a 1.4 fWAR.

The next major trade was Joe Musgrove to the San Diego Padres. Musgrove showed the talent to be a good starting pitcher but consistently ran into some bad luck, mainly because of poor defense on the Pirate end. The Pirates ended up getting back a four-player package for the right-hander.

While Hudson Head was considered the headliner at the time of the trade, you wouldn’t have guessed that based on Endy Rodriguez and David Bednar’s performances this year. The switch-hitting catcher, Rodriguez won the Low-A Southeastern League MVP after posting outstanding numbers.

Bednar, the Mars native, looks to open 2022 as the major league team’s closer. Head showed a strong ability to draw walks and hit for some power, but his swings and misses stood in the way of a good season. Though he’s still fairly young and is considered a high-ceiling, highly athletic outfielder. Omar Cruz pitched mostly at Double-A this year where he put up solid results. He’ll likely start 2022 at Triple-A Indianapolis and could make an impact at the major league level in 2022. The fourth and final player was Drake Fellows, who only pitched 11.2 innings between the FCL and Bradenton. He’s a forgotten man in the draft, but still a player to keep watch on in 2022.

The next big trade was when they sent Jameson Taillon to the New York Yankees. Despite Taillon coming off his second career Tommy John surgery and not pitching more than 150 innings just one time throughout his career up to the trade, the Pirates were still able to get back a four-player prospect package, one that could be a franchise changer.

The headliner at the time was Miguel Yajure. A control/command-oriented pitcher, Yajure showed off some solid stuff in the major leagues. He did have one big blow-up outing at the end of the year, but had it not been for an injury, he would have likely gotten an extended look in the major leagues this year. Roansy Contreras has developed into one of baseball’s most notable pitching prospects. The right-hander saw a huge uptick in velocity, going from the low-to-mid-90’s to the upper-90’s this year. Plus with a strong breaking ball, above-average change-up, and good command, he could be one of the Pirate standout starting pitchers.

Outfielder Canaan Smith-Njigba had a good season at Double-A and was promoted to Triple-A at the tail-end of the season. He could make an impact on the Major League team next season. Finally, there’s Maikol Escotto. The infielder showed off some promise at Low-A Bradenton, but only had a 100 wRC+. Still, he’s only 19-years-old and won’t turn 20 until next June. Escotto has very good power potential and has shown off a strong ability to draw walks. He just needs to strike out less and lower his ground ball rate. Taillon would go on to have just a 100 ERA+ and 2.0 fWAR. While not awful, he wasn’t any better than Tyler Anderson.

Approaching this year’s deadline, Cherington took advantage of Adam Frazier’s hot streak. Frazier was having a strong season at the time, but Frazier was showing signs of slowing down at the time of the trade with a .730 OPS and 100 wRC+ in the month leading up to the swap. Plus he had a high batting average on balls in play. The Bucs decided to deal the utility man to the San Diego Padres for a three-player prospect package.

The best prospect to come out of the deal was a utility prospect by the name of Tucupita Marcano. Marcano went directly from Low-A all the way to the major leagues from 2019 to 2021. He didn’t play at any other level before making his Major League debut, so it’s understandable why he struggled in his small sample size of plate appearances (50).

Still, Marcano has been highly praised by scouts for his hand-eye coordination and his ability to put the bat to the ball. He’s also shown a good ability to draw walks, along with avoiding strikeouts. Plus he’s athletic and can play multiple positions. Jack Suwinski is a power-hitting outfielder but does have his struggles when it comes to strikeouts. He has some sneaky athleticism which lets him move around well in the outfield while also having a strong arm. The last player involved was Michell Miliano. The right-handed relief prospect has a big fastball but struggles greatly with command. Though the Padres saw Frazier hit for just a .662 OPS and 85 wRC+ so far.

The other big trade around the deadline was Richard Rodriguez. Rodriguez, like Frazier, had a great start to the 2021 season but was showing signs of slowing down. He was one of the main pitchers affected by the crackdown on sticky substances, so with that, the Pirates moved him at the deadline for two pitching prospects; Bryse Wilson and Ricky DeVito.

Wilson was once one of Atlanta’s top 10 organizational prospects, even before the likes of Ronald Acuna Jr., Austin Riley, Mike Soroka, and Ian Anderson would graduate prospect status. Wilson showed some potential as a solid #4 starter during his time with the Pittsburgh Pirates so far but needs to show a better ability to go deeper into games. Ricky DeVito on the other hand had a good start to the 2021 season at Low-A but was held to just 20.1 innings because of an injury.

While DeVito doesn’t project as a top-of-the-line pitching prospect, there’s still a solid pitcher in the right-hander. Whether or not he’ll work out of the rotation or bullpen will remain to be seen, but he has shown off some good stuff, including an impressive splitter. Rodriguez post-trade saw a huge decline in effectiveness. While he did have a 3.12 ERA, that was supported by an extremely unsustainable .200 batting average on balls in play. He gave up 6 long balls in just 26 innings (2.08-per-9), walked 5, only struck out 9, and was even left off the Braves’ postseason roster.

The team also made a handful of smaller deals around the deadline. This included sending Tyler Anderson to the Seattle Mariners for Joaquin Tejada and Carter Bins, trading Austin Davis to the Boston Red Sox for Michael Chavis, and then moving Clay Holmes to the New York Yankees for Diego Castillo and Hoy Park.

While the Josh Bell trade doesn’t look good so far, the Joe Musgrove trade looks like it could be a win-win trade. The Taillon trade has the potential to be the Pirates’ version of the Archer trade (knock on wood). While I also think the Adam Frazier trade is blown way out of the water by some fans, it still feels like the team could have foregone either Suwinski and/or Millano for a slightly better headliner. The Rodriguez trade may be more of a forgotten deal, but the Pirates got two pitchers who have some potential for a reliever who’s struggled with command since losing the sticky stuff. I also think Cherington did well in the smaller trades. Getting anything for Austin Davis was a plus and Diego Castillo looks like he could be a starting infielder for the Pirates next season.

If you want a different prespective from the trades, the only player of high value that was traded (ie Bell, Musgrove, Taillon, Frazier), only Taillon’s team, the Yankees made the playoffs, albiet in the second Wild Card spot and lost to the Red Sox (unless you consider Rodriguez and the Braves who are on their way to the ALCS, but with him not part of the roster).

Grade: B
While he seems to have done very well on some trades, others have given the Pirates a less-than-favorable return so far. But none of the trades have been downright awful.

Major League Team

I will preface this by saying that Cherington’s focus was likely more on the development of players throughout the minor leagues and certain ones at the major leagues, though the performance of the major league team probably wasn’t at the forefront of his focus. That is something I will take into consideration when giving his final grade.

The Pirates finished with the 4th worst record in all of baseball, coming in with an abysmal 61-101 record. The likes of Kevin Newman, Gregory Polanco, Chad Kuhl, and Wil Crowe were all in starting roles. Both Colin Moran and Ke’Bryan Hayes missed a good chunk of the season because of hand injuries, likely contributing to their underperformance this year. Many starting pitchers failed to go deep into games and the bullpen was overtaxed multiple times this year.

I could sit here all day and point out the negatives about the major league roster, but there were a few positives. For one, Bryan Reynolds bounced back in a big way. He ended the season with .385 wOBA, 142 wRC+, and tied with Aaron Judge and Brandon Crawford for the 9th best fWAR at 5.5. David Bednar became a high-quality reliever, posting a 2.23 ERA, 2.69 FIP, and .973 WHIP in 60.2 innings of work. He was one of 25 qualified relievers with a WHIP below 1. Ben Gamel proved to be a solid waiver claim, and Tyler Anderson provided the Pirates 5 solid innings every 5th day up until his trade. During the home stretch of the campaign, the Pirates picked up Yoshi Tsutsugo, which turned out to be an outstanding depth pick-up. Even Anthony Alford and Cole Tucker. Plus we got a glimmer of the future with both Roansy Contreras and Oneil Cruz making their debuts in the final week of the season.

Still, 101 losses speak for themselves. Depending on who you ask, this could be a good thing as it gives the Pirates another very high draft slot or a bad thing as it felt the season was on a continuous downward spiral. Even if the team has improvement on the horizon and started to show some glimmers of hope at the end of the season, overall it was a poorly put-together major league 26-man roster.

If you want a slightly more positive outlook on the Pittsburgh Pirates final record, they finished the second half (27-45) with a very similar record to both the New York Mets (29-45), San Diego Padres (26-43), and an identical record to division rival the Chicago Cubs.

F+
Sure, the major league team may not have been the primary focus for Cherington, but the final results, even for a rebuilding team, were poor.

Overall And Final Thoughts

Ben Cherington had quite an active year between October 2020 and October 2021. He traded a handful of players, had a very impressive draft, an active trade deadline, and saw many of his organization’s best prospects take steps forward.

There’s still work to be done, and there have been some rough patches. But overall, Cherington has provided the Pittsburgh Pirates with a positive outlook on the future. He’s vastly improved the farm system through trades and drafting. What happens next remains to be seen, but I’m looking forward to it based on what he’s done so far.

Final Grade: B+
Ben Cherington has given the team a very hopeful future. While some of the returns for trades have been a bit questionable, the draft, development of players, and other trades that look good are why Cherington has gotten praise by many for his rebuild so far.