Grading Pirates GM Ben Cherington’s trades so far

The trade deadline is always a fun and interesting time for baseball fans anxious to find out who’s moving where and what impact it will have on the pennant races. For Pirates fans in recent years, it’s been all about which of their favorite players are being dumped for prospects. Former general manager Neal Huntington used to justify these deals by saying he acquired “years of control.” I’d thought about buying a Pirates jersey with the words “Years of Control” emblazoned where the player’s name would be.

Rather than focusing on the upcoming deadline, I thought it would be more interesting to evaluate the 11 trades general manager Ben Cherington has made so far since taking over in 2019. Where you see a number after the player’s name, that’s his ranking among Pirates prospects, per

Rebuilding begins again

January 27, 2020: OF Starling Marte to the Arizona Diamondbacks for SS Liover Peguero (5) and P Brennan Malone (27). Marte is a graceful, five-tool player and one of baseball’s most underrated stars. In his eight years as a Pirate, he hit .287/.341/.452, 108 HR, 420 RBIs, 239 SB. But toward the end, he was said to be unhappy in Pittsburgh and anxious to play for a contender.

The key to the deal, Peguero is a slick fielder and plus runner who hits the ball hard. Presently at double-A Altoona, clearly he was acquired with the thought that he’ll be the Pirates shortstop of the future. Of course, Oneil Cruz, their third-ranked prospect, might have something to say about that. The six-foot-four, 205-pound Malone has a fast ball that reaches 97 MPH. He’s only 21 years old and has yet to pitch as high as double-A. Both project to be impact players in the future. Grade: A.

For whom Bell tolls

December 24, 2020: 1B Josh Bell to the Washington Nationals for P Wil Crowe and P Eddy Yean. In 2019, Bell hit .277/.367/.569, 37 HR, 116 RBIs and made the All-Star team. He declined a bit in the COVID-shortened 2020 season. Then again, different players reacted differently to the hastily arranged preseason preparation time. Crowe was immediately major-league ready, so-so as a starter in 2021 but blossoming in the bullpen in 2022. Yean was the Nationals’ sixth-ranked prospect at the time of the trade. However, he’s not listed among the Pirates’ top prospects. A mere 21 years old, in his two seasons in A-ball as Pirates property, his ERA, WHIP and walk ratio have been alarmingly high.

Bell is presently the subject of trade rumors himself. He becomes a free agent in 2023, whereas Crowe isn’t eligible until 2027. Oh, those precious years of control! Nothing says Yean can’t develop into a major-league pitcher. For now, though, the trade looks like one of a once-All-Star slugger for a middle reliever, albeit a very good one. Seems three years of Bell should have fetched just a little more. Grade: B.

Hey, Joe, where you going with that glove in your hand?

January 19, 2021: P Joe Musgrove to the San Diego Padres for P David Bednar , C-OF Endy Rodriguez (6), OF Hudson Head (18), P Omar Cruz and P Drake Fellows. Wow! Musgrove, of course, has been good for the Padres. But Bednar is arguably the best relief pitcher in baseball. He should make the All-Star team if there’s any justice in this world. He’s the only one of the five acquired who’s made it to the Pirates so far. Endy Rodriguez has the tools to be an excellent catcher, is athletic enough to play some outfield and has been a good minor-league hitter. The Pirates’ number-one prospect, Henry Davis, is also a catcher. But the position has taken on increased importance in today’s game. No manager wants to have a significant drop-off when the backup plays.

Head has speed and power and is also a good athlete, although statistically he’s regressed quite a bit. Omar Cruz and Fellows are each 23 years old and haven’t put up good minor league numbers yet. But Fellows played three years at Vanderbilt, an excellent NCAA baseball program. To think Musgrove was just one of four players acquired for Gerrit Cole. Now he’s fetched five players on his own! Grade: A.

Last trade of a busy winter

January 24, 2021: P Jameson Tallion to the New York Yankees for P Roansy Contreras, SS Maikol Escotto (16), OF Canaan Smith-Njigba (20) and P Miguel Yajure. It goes without saying the Yankees have to be ecstatic over Tallion’s performance this year. However, Contreras has flashed enough ability for the Pirates to show he’s an emerging staff ace. The 20-year-old Escotto signed with the Yankees in 2019 and turned a few heads with a .315/.429/.553 slash line in the Dominican Summer League.

Smith-Njigba is another in the long line of left-handed hitting outfielders the Pirates are stockpiling, presumably to take advantage of PNC Park’s short right field. His numbers so far have been good, but not outstanding, although the Pirates saw enough to reward him by recalling him to the big club before an unfortunate injury ended his season after three games and seven plate appearances. Yajure has an 8.16 ERA and 5.7 walks per nine innings in triple-A as I write this. Despite those depressing numbers, the Pirates have given him cameo appearances in the majors in 2021 and 2022. Grade: A.

Out goes Frazier

July 26, 2021: 2B-OF Adam Frazier to the San Diego Padres for OF Jack Suwinski, IF-OF Tucupita Marcano and P Michell Miliano. Frazier was a starter in the All-Star Game in 2021 and a hot commodity on the trade market. Pirates fans hated to see yet another trade of a player who was playing well. Frazier was hitting .324/.388/.448 at the time of the deal. However, the analytics geeks warned those numbers weren’t sustainable, given an accompanying 26.3 percent Hard Hit Rate. Chalk one up for the nerds. Frazier went on to hit .267 for the Padres, who didn’t deem him worthy of keeping after the season. He is now hitting .223 for the Seattle Mariners after 83 games.

Meanwhile, Suwinski leads all National League rookies with 14 home runs as I write this, after making the jump to the majors directly from double-A. Marcano has been with the big club this year and looks to be a useful versatility option. Through five minor league seasons, Miliano has a 6.45 ERA and an alarming 8.7 walks per nine innings ratio and does not appear to be a prospect. Grade: A.

Feet of Clay

July 26, 2021: P Clay Holmes to the New York Yankees for IF-OF Diego Castillo and IF-OF Hoy Park. For many of us, there’s always one obstacle to a good report card. It was chemistry class for me. For Cherington, it’s this trade. As a Pirate, Holmes had a 5.57 ERA and a 1.638 WHIP over parts of four seasons. As a Yankee, he has a 0.95 ERA and a .742 WHIP. This year, he’s been the best reliever in baseball not named Bednar, at 4-0, 16 saves, 0.47 ERA and .711 WHIP in 37 games, all at a bargain $1.1 million salary.

Is it just the product of being on a better team? Let’s take a look at his FIP, which takes the defense playing behind him out of the equation. Holmes had a 4.72 FIP as a Pirate and has a 1.86 FIP as a Yankee. No, the Pirates clearly missed something. Could they have foreseen this success? According to recent comments by his former teammates, the answer is yes.

Castillo and Park are decent defenders all over the infield. Park is the better outfielder while Castillo is learning on the job. Castillo’s 10 homers rank third in the league for rookies. However, after a hot start he has provided little else on offense. Park has an impressive .368 OBP over seven minor league seasons. Neither figures to be a regular with the Pirates in the long run. Not with the infield of the future destined to be Ke’Bryan Hayes at third, either Oneil Cruz or Peguero at shortstop and former number one draft pick Nick Gonzales at second. Hindsight is 20/20 but Holmes should have garnered a better return than two utility men. Better yet, the Pirates should simply have retained him. Grade: D.

Time will tell

July 27, 2021: P Tyler Anderson to the Seattle Mariners for C Carter Bins and P Joaquin Tejada. Anderson came to the Pirates on a team-friendly one-year deal, the 2021 version of the veteran starter who was supposed to pitch decently while mentoring the youngsters, before being traded for hot prospects. By all accounts, he was a good teammate, so he checked that box. With occasional good starts, as a Pirate he was 5-8 with a 4.35 ERA. Anderson yielded two players not ranked among the Pirates’ top prospects.

Bin was invited to the Pirates’ spring training as a non-roster player, although that may have been because major-league teams like to have a surplus of catchers to accommodate all of the pitchers in camp. Bin was also promoted to triple-A on May 10. His minor league stats suggest he wasn’t acquired for his bat. He has a below-average 21 percent caught stealing rate in the minors. There are no stats available to indicate whether he has the pitch-framing skills the Pirates covet. Tejada is only 18 years old. I’ll need a few more years to evaluate this transaction. Bet you can’t wait. Grade: Incomplete.

Deadline day 2021 begins

July 31, 2021: P Braeden Ogle to the Philadelphia Phillies for C Abrahan Gutierrez. Say what? That was the reaction of Pirates fans who spent the work day constantly refreshing the many baseball sites when they saw this one pop up as the Pirates’ first deal on deadline day. (As for whether I was one of them, I hereby take the Fifth.) Neither is among his new team’s ranked prospects. Gutierrez was to be a throw-in a larger trade with the Phillies that had fallen through. But Cherington thought highly enough of him to go back and negotiate a separate deal to acquire him. Give Cherington credit for keeping his eye on the ball and acquiring some organizational catching depth when he had bigger fish to fry. Grade: B.

“Rich-Rod” to Atlanta

July 31, 2021: P Richard Rodriguez to the Atlanta Braves for P Bryse Wilson and P Ricky DeVito. After former closer Felipe Vazquez‘s (ahem) legal troubles, Richard Rodriguez assumed the role and picked up four saves in 2020 and 14 more in 2021 before being dealt. In four years as a Pirate, Richard Rodriguez had a highly respectable 2.98 ERA, 1.09 WHIP and 4.19:1 strikeout to walk ratio despite pitching on bad teams.

Wilson went to the big club immediately but has been maddeningly inconsistent, resulting in being shuttled back and forth from the minors in 2022. Recent starts have been better, beating the Brewers on July 2 and losing to the Reds five days later due to bad defense behind him. Although not a ranked prospect, the 23-year-old DeVito’s numbers aren’t bad: a 3.63 ERA over three minor league seasons and a 2.60 ERA over three NCAA seasons pitching for Seton Hall. There’s no reason to think either of these gentlemen won’t pan out for the Pirates. Neither is it a sure thing either. Grade: C.


July 31, 2021: P Austin Davis to the Boston Red Sox for IF Michael Chavis. In exchange for a seldom-used relief pitcher, the Pirates picked up one of their better offensive contributors. Chavis’s present stat line of .238/.279/.432, 9 HR, 29 RBIS belies his true worth, as so many of his hits have come at opportune times for the Pirates. He’s a fiery, personable guy who’s fun to watch. He was a number one draft pick of the Red Sox when Cherington was there. To these eyes, he fields the second base spot well, but manager Derek Shelton views him as a corner infielder. Grade: A.

A shocker

November 29, 2021: C Jacob Stallings to the Miami Marlins for P Zach Thompson, P Kyle Nicolas (17) and OF Connor Scott (26). Pirates fans choked on their leftover turkey when this news hit. In 2021, Stallings had won a Gold Glove Award, emerged as a team leader and drew high praise for his work with the pitchers. He knew he would one day step aside for Davis and was on record as being content to mentor him in a reserve role.

Of the trio acquired, Thompson is the only one on the big league roster and thus the only tangible evidence of the trade to Pirates fans so far. At the end of April, he was 0-3 with a 10.05 ERA, doing little to make the fans happier about the trade. He’s been better afterward, however, and is now 3-6 with a 4.42 ERA. The six-foot-four, 223-pound, 23-year-old Nicolas was believed to have been the key to the trade. His minor league numbers aren’t great but he has drawn high praise from scouts for his velocity and ability to maintain it during long outings. Similarly, the 22-year-old Scott’s numbers don’t jump out at you, but scouts like his speed and contact rate. Grade: B.

This gives Cherington a 3.2 Grade Point Average through the end of 2021. Congratulations, Ben, you’ve made the Dean’s List! Please print this, have it signed by a parent and return it to me.

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