Ben Cherington's Long-Term Trade Outlook Will Lead to Sustainable Success

Photo Credit: Christopher Horner/Tribune-Review

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**Prospect rankings for this blog were sourced from and all contract info was sourced from Spotrac.**

GM Ben Cherington (GMBC) is proving to be quite the wheeler and dealer so far in his career with the Pittsburgh Pirates.  He recognized the bare cabinet he was inheriting and how it lacked young players with years of control that could make an impact at the major league level.  While he has dealt players that have went on to have success elsewhere, some of those players would have already been lost to free agency anyway, or very close to it.  So instead of letting those veterans accumulate stats as a Pirate and walk away, he has loaded the Pirates farm system with players that will lead to sustainable success.

A few perfect examples of this are Liover Peguero, Brennan Malone, and Wil Crowe.  Wil Crowe has been very successful this season in the bullpen and is under team control until 2026.  Peguero (#5) and Malone (#29) are both top prospects, and have yet to have their clocks start.  Each are just 21 years old.

Peguero and Malone were acquired for Starling Marte, and Wil Crowe was acquired for Josh Bell, who are both performing decently for other teams.  However, Bell is an unrestricted free agent at the end of this season, and Marte already hit free agency before signing a massive deal with the New York Mets.  So with the new window of success just beginning, both would have been gone anyway.

Further great examples of loading the farm system with controllable assets in exchange for aging players are the two trades GMBC made at the beginning of 2021.  In January of last year, two currently successful starting pitchers were traded: Joe Musgrove and Jameson Taillon.  

Currently, Jameson Taillon is 6-1 for the New York Yankees this season with a 2.30 ERA and 0.90 WHIP.  These are very impressive numbers.  However, Taillon already hit free agency once, and will do so again after this season barring a midseason extension from the Yankees.  Meanwhile, budding superstar, Roansy Contreras, was received in return for Taillon, among Miguel Yajure, Maikol Escotto, and Canaan Smith-Njigba.  

Any excitement over Yajure has fizzled out as of late, but Contreras is the first appointment-television starting pitcher the Pirates have had since Gerrit Cole.  Contreras is also only 22 years of age and in the pre-arbitration terms of his contract.  He will be successful for the Pirates for a long time to come. and I don't want to fail to mention that Smith-Njigba (#21) and Escotto (#17) are both top prospects for the Pirates as well.

Also, while Joe Musgrove has been nothing short of outstanding this season, so has David Bednar.  Musgrove may win the NL Cy Young Award, and will surely be in the All-Star Game in July, but Bednar will be right beside him.  In addition to receiving Bednar in the Musgrove trade, the Pirates received #7 prospect Endy Rodriguez and #20 prospect Hudson Head in the deal.  

With how great Joe Musgrove has been since leaving the Pirates, this one is a little tougher to swallow.  However, when you consider that Rodriguez's and Head's clocks haven't started yet, and Bednar is still under team control until 2026, it levels it out a bit.  Meanwhile, Musgrove will surely hit unrestricted free agency this offseason and sign a massive deal with one of the New York or LA teams.  They may be the only teams who can afford him after this season.

Then there are a couple absolute steals that occurred at the deadline last season and this past offseason.  Adam Frazier was traded for Tucupita Marcano and Jack Suwinski.  Suwinski and Marcano are controllable youngsters who have directly led to wins this season and show no signs of slowing down.  Suwinski hit a walkoff homerun on Saturday to beat the Arizona Diamondbacks and Marcano is 8 for 29 with two homeruns and two doubles so far.  For the Mariners this season, Frazier is batting .238 and looks like his best seasons are behind him.

GMBC also traded 32 year-old Jacob Stallings this offseason to the Miami Marlins for Zach Thompson, Connor Scott, and Kyle Nicolas.  As of late, Zach Thompson has been one of the Pirates' best starting pitchers.  In his last seven appearances, he's 5-2 with a 2.05 ERA.  Opposing hitters are batting just .211 against him.  More importantly he's given up just three homeruns in that span.  

Also, #18 prospect Nicolas and #28 prospect Scott have played decently well for AA-Altoona this season.  Stallings is batting just .208, and with just 1 homerun and 18 RBI in 129 at-bats this season, he's not even providing the occasional spark we saw from him with the Pirates last year.

We continue to see players acquired by GMBC making an impact at the major league level already or improving in the minor leagues.  And while it'd be nice to see more homegrown guys make an impact and rise the ranks, knowing we acquired these pieces by trading players with expiring contracts makes it all the better.  Having a roster full of talented players with controllable contracts for the next 3-6 seasons will lead to sustained success.  We're already in the midst of a nice little run here.  Won't it be nice to see it extended for years to come?