Blue Jays: Potential Trade Scenarios with the Pittsburgh Pirates

MILWAUKEE, WISCONSIN - JUNE 30: Starling Marte #6 of the Pittsburgh Pirates celebrates in the dugout with teammates after scoring in the first inning against the Milwaukee Brewers at Miller Park on June 30, 2019 in Milwaukee, Wisconsin. (Photo by Quinn Harris/Getty Images)
MILWAUKEE, WISCONSIN - JUNE 30: Starling Marte #6 of the Pittsburgh Pirates celebrates in the dugout with teammates after scoring in the first inning against the Milwaukee Brewers at Miller Park on June 30, 2019 in Milwaukee, Wisconsin. (Photo by Quinn Harris/Getty Images) /

Ben Cherington has accepted the offer to become the new General Manager of the Pirates according to the Pittsburgh Post-Gazette. Given his responsibility for player development in Toronto since September 2016, he knows the Jays farm system inside-out. So who might be involved in potential trades between the Blue Jays and the Pirates?

While the Blue Jays organization is losing its VP of Baseball Operations, Ben Cherington has been interested in an opportunity that would allow him to “build an organization from the ground up”. The Pittsburgh Pirates certainly fit the bill, with a proud history and five World Series Championships, but none since 1979.

The current team, which had a similar 2019 record as the Blue Jays at 69-93, features some pieces to build around, including 24-year old LF Bryan Reynolds, 26-year old starter Joe Musgrove, 26-year old SS Kevin Newman, and 27-year old 1B Josh Bell.

Looking back at some of the moves Cherington made as GM in Boston might point to potential trade targets for the Blue Jays front office. Mark Shapiro knew him from when they overlapped in 1998 in the Cleveland Indians organization, when Cherington was an advance scout and Shapiro was the team’s minor league director.

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We’ve seen Shapiro and Ross Atkins make a number of deals with their former team, including trading reliever Joe Smith to the Indians for infielder Samad Taylor (minors) and lefty Thomas Pannone at the July 2017 trade deadline, trading for 3B Gio Urshela in May 2018, and trading 3B Josh Donaldson at the August 31, 2018 waiver deadline for injured minor leaguer Julian Merryweather. Atkins knew these players from his time as Indians vice president of player personnel through 2015, and had previously worked with Indians GM Mike Chernoff.

Given Cherington has similar knowledge of the Blue Jays system, could he look to make deals with his former colleagues in Toronto? Studying his past moves might provide some clues.

The Boston Years – Mixed Record After Chicken and Beer

After replacing Theo Epstein as Boston GM in October 2011, Cherington helped build the Red Sox World Series Champions in 2013, but resigned less than four years later after Dave Dombrowski was hired to oversee him. While his teams finished in last place in the AL East in 2012, 2014, and 2015, he did help to develop the young 2018 World Series Champion core.

Cherington inherited a disaster from Theo Epstein after the 2011 season. The organization was in disarray. Just two weeks before his promotion to GM, Bob Hohler of the Boston Globe had written a damning account of the greatest collapse in MLB history: the $161 million Red Sox became a laughingstock, going 7-20 down the stretch and blowing a two game AL East lead over the Yankees, and a nine game wild-card lead over the Rays, to finish out of the playoffs. According to Hohler:

"Boston’s three elite starters went soft, their pitching as anemic as their work ethic. The indifference of Josh Beckett, Jon Lester, and John Lackey in a time of crisis can be seen in what team sources say became their habit of drinking beer, eating fast-food fried chicken, and playing video games in the clubhouse during games while their teammates tried to salvage a once-promising season… How a team that was on pace in late August to win 100 games and contend for its third World Series title in seven years self-destructed is a story of disunity, disloyalty, and dysfunction like few others in franchise history."

Manager Terry Francona left after the season, and Theo Epstein was hired by the Chicago Cubs to be their President the same day the Boston Globe expose of the September collapse was published. There was lingering resentment in the clubhouse. In their postseason remarks, the ownership group claimed they were generally unaware of how deeply damaged the Sox had become until after the season.

Epstein’s trades and free agent signings hadn’t worked out:  Adrian Gonzalez was acquired from San Diego, and while he strengthened the middle of the Sox lineup, he didn’t become a leader. Free agents John Lackey (5 years/$82.5 million) and Carl Crawford (7 years/$142 million) had been busts. Interestingly, it was Cherington who’d been the strongest advocate of signing Crawford, pushing Epstein and ownership to sign him.

Building the 2013 World Series Champs

Looking at the key moves Cherington made as the architect of the 2013 Red Sox might suggest what he’ll look to do with the Pirates:

  • Trade expensive multi-year contracts and older players. During the forgettable 2012 season, he traded 32-year old 1B Kevin Youkilis and cash to the White Sox. 35-year old Marco Scutaro was moved that January to free up cash. In a waiver deal that August, he traded Carl Crawford, Adrian Gonzalez, Josh Beckett and Nick Punto to the Dodgers for Ivan De Jesus, James Loney, Allen Webster, Rubby De La Rosa and Jerry Sands. The move freed up $262.5 million in salary obligations , which allowed him to rebuild ahead of 2013.
  • Manager. Cherington hired former Red Sox pitching coach John Farrell as his manager that October 2012 in a trade with the Blue Jays for infielder Mike Aviles.
  • Emphasize player development, but surround the young core with veteran talent.  Cherington signed seven key free agents for the World Series run in Shane Victorino, Mike Napoli, Jonny Gomes, Ryan Dempster, David Ross, Koji Uehara, and Stephen Drew. He traded for Mike Carp from Seattle and Brock Holt from Pittsburgh before the start of that year. At the July 2013 trade deadline, he traded Jose Iglesias and prospects in a three-team trade with Detroit and the White Sox, which brought back starter Jake Peavy.
  • Draft well and sign international talent. That August 2013, he signed future star 3B Rafael Devers and LHP Darwinzon Hernandez as international amateur free agents.
  • Good luck & intangibles. Stars David Ortiz, Jacoby Ellsbury and John Lackey would all return to health, and the emotion of the Boston Marathon bombing gave them extra inspiration. The 2013 team improved by 28 wins, going from last place and 26 games back to a 97 win season and World Series Championship.

Aggressive Rebuilding & Young Core

The 2014 Sox would collapse again; by July 26th they were 10.5 games back in the AL East at 47-57 and Cherington would dismantle the team:

Potential Lessons

The Pirates were 25-48 (.342) after the All-Star break this year, finishing 5th in the NL Central, 22 games behind St. Louis. So as he rebuilds the Pirates, could Cherington could look to move older players like he did in 2012 with Boston, trading away Youkilis and Scutaro, as well as players with multi-year control like A-Gon, Beckett and Crawford?

He will also need to hire a new manager to replace Clint Hurdle, who by all accounts lost control of the clubhouse in 2019 much like Terry Francona did in Boston in 2011.

There are lingering clubhouse problems; the Pirates issued suspensions after altercations involving coaches and two relievers, Keone Kela and Kyle Crick. Kela also received a 10-game suspension for starting an altercation with the Reds in late July. Closer Felipe Vazquez was arrested in September and has been suspended as he faces criminal charges for sexual assault.

As Rob Biertempfel wrote in The Athletic,

"many inside the Pirates organization believe part of the problem is that there are no veteran leaders such as Andrew McCutchen, David Freese, or Josh Harrison to deal with the small frictions which lead to the big blowups. The Pirates, of course, have sent off any number of veterans in recent years in primarily cost-cutting moves."

No doubt Cherington was hired in Pittsburgh given his record on player development. 24-year old LF Bryan Reynolds, 26-year old starter Joe Musgrove, 26-year old SS Kevin Newman, and 27-year old 1B Josh Bell are potential players to build around. The top-heavy farm system has three top-100 MLB prospects in RHP Mitch Keller (MLP Prospect ranking #26), 3B Ke’Bryan Hayes (the son of former major league 3B Charlie Hayes is ranked #36), and SS Oneil Cruz (#57), but ranks 19th overall according to Baseball America.

Cherington also signed veteran free agent talent to surround the young core developed in Boston. Whether or not the payroll constrained Pirates will allow him to sign free agents remains to be seen, but he does have a past history of trading for both 30-year old Rick Porcello and 33-year old Wade Miley in Boston. Both starters are available in free agency, which could put him in direct competition with the Blue Jays front office this offseason.

The low-budget Pirates opened 2019 with a payroll of $74.8 million, but Spotrac has them committing $71 million at present using MLBTR’s estimates for arbitration salaries. Assuming no non-tenders, and that Vazquez’s $5.75 million contract is voided, plus $6-7m for the pre-arbitration players on the 26-man roster, Cherington might have approximately $25 million in additional salary budget if owner Bob Nutting is willing to return an Opening Day payroll of over $90 million where it was each season from 2015-17. That might be enough for him to get Porcello (MLBTR estimates 1 year/$11 million) and Miley (2 years/$16 million).

Potential Trades Scenarios

Given Cherington’s knowledge of the Blue Jays farm system, could he ask for prospects for some of the veteran trade chips he now has in Pittsburgh?  The Pirates need starting pitching, a closer, a catcher, and a third baseman. The Blue Jays have identified needs in starting pitching, CF and 1B which could match well with some of the potential Pirates trade chips:

  • 31-year old CF Starling Marte who is on a friendly $11.5 million dollar deal in 2020 with $12.5 million club option for 2021
  • 31-year old former Tampa Bay Rays starter Chris Archer, who has been regressing since 2015, and pitched poorly in 2019, but is on an affordable $9 million dollar deal in 2020 with an $11 million club option for 2021
  • 28-year old RF Gregory Polanco who was on the 60-day IL after left shoulder surgery in September 2018, but is under team control until 2023
  • 26-year old set up man Keone Kela who will be an UFA in 2021, but who was suspended for 10 games after instigating a bench clearing brawl with the Reds in late July, and who got into a shouting match with performance coach Hector Morales, and then berated manager Clint Hurdle when he tried to calm everyone down
  • Soon to be 27-year old reliever Kyle Crick, who engaged in a clubhouse fight with closer Felipe Vazquez, which resulted in season-ending tendon surgery in his right index finger plus fines for both pitchers; Crick previously feuded with bullpen coach Euclides Rojas over alleged preferential treatment the latter gave Vazquez
  • 28-year old closer Vazquez (5-1, 28 saves, 1.65 ERA over 60 innings pitched with 90 Ks), who may never pitch in MLB again given he’s facing criminal sexual assault charges; his $5.75 million contract could be voided depending on the court ruling and league discipline

Cherington is most certainly going to go into rebuild mode with Starling Marte ($11.5 million due with a $12.5 million club option in 2021), Chris Archer ($9 million due with an $11 million club option in 2021), and Gregory Polanco ($19 million due over the next two seasons, with club options in 2022 and 2023). Moving these three would get $45 million off the books, including buyouts. He’ll need to rid the clubhouse of troublemakers Kela and Crick, and replace closer Vazquez. 1B Josh Bell (2.9 bWAR, OBP .367, OPS .936, OPS+143) is a Scott Boras client and is under team control until 2022, with a projected arbitration salary of $5.9 million in 2020, so he’d be valuable trade capital.

Marte was suspended 80 games in 2017 for violating MLB’s Joint Drug Prevention and Treatment Program, but he’s bounced back with an .816 OPS, 43 homers, 58 steals and 6.6 WAR over the last two seasons. With no star CFs on the open market, Marte will likely have interest from the Jays, Mets and Padres (who are clearly willing to move prospects).

Jays Trades

CF Starling Marte would help improve the Jays team OBP .305 and weak OF defence. He also has an attractive contract with the club option for 2021.

1B Josh Bell is under team control until 2022, with a projected arbitration salary of $5.9 million in 2020; he would also help improve the Jays on-base percentage with his career OBP .354 and OPS .831 but would cost much more for his three years of team control.

Starter Chris Archer is also on a team-friendly contract with the club option for 2021. Cherington may just want to move on from him given the lopsided trade of Austin Meadows, Tyler Glasnow and minor league starter Shane Baz consummated by his predecessor Neal Huntington? The Jays may not be interested given Archer is best friends with former Jay Marcus Stroman, who did not leave Toronto on good terms with the front office this past July.

Who could the Jays package in a deal for Marte?

The Jays have potential surplus assets to trade at catcher given minor league depth at the position. Would a package built around 19-year old Lansing Lugnuts catcher Gabriel Moreno (FanGraphs Future Value 40+) and two lesser prospects that Cherington likes be enough to get Marte?  Or would he prefer the more developed AA catcher Riley Adams (FV 40+)? Or could Atkins really be looking to sign free agent catcher Yasmani Grandal (MLBTR estimates 4 years/$68 million), and then trade one of Danny Jansen or Reese McGuire (who was drafted #14 overall by the Pirates in 2013) in a package?

If they packaged closer Ken Giles and Reese McGuire, who is under team control until 2024, could they add two lower level prospects and get both Josh Bell and Starling Marte?

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Cherington knows the Blue Jays system and will likely look to make deals with his former colleagues in Toronto. With an expected rebuild in Pittsburgh, or at least a retool, we know from his past rebuilds in Boston that he will look to move his costlier, multi-year contracts for players like Marte, Archer and potentially also Josh Bell. These players fill clear needs for the Blue Jays, who can deal from strengths in catching. Let’s hope there are deals to be made.