Red Sox History: Boston plays ‘Deal or No Deal’ at the Trade Deadline

A look at past Red Sox deadline deals

For Boston Red Sox fans the “I’m Shipping up to Boston” time is in the works – maybe. Just what deals will Chaim Bloom and his staff execute? Will they add bullpen strength such as an Eric Gagne in 2007? As far as disasters, that classifies as a baseball Titanic. That, however, could be offset by Dave Roberts arriving at deadline time in 2004.

Roberts is synonymous with “The Steal.” A minor transaction, but that transaction was a blip since the big one that day was Boston getting Orlando Cabrera and Doug Mientkiewicz in a three-team deal. Gone was Nomar Garciaparra. The deal changed the internal and external Red Sox. Defensively a significant and necessary upgrade. And clubhouse dynamics were also upgraded by the departure of Nomar.

The debate is sometimes centered on prospects as it is with the now. Do you trade a prospect(s) for the here and now? Does the prospect turn out to be Jeff Bagwell? A deal that looked solid at the time. That is risky territory and in 2013 the Red Sox took that risk. The short-term results were a key piece for a championship.

The Red Sox needed some rotation depth – a tune we hear whistled every year. The Red Sox sent Jose Iglesias to the Tigers in a rather expansive three-team transaction. Boston received former Cy Young winner right-hander Jake Peavy in return. Peavy (4-1, 4.04) had enough left in the tank to give the Red Sox a boost into another flag. Iglesias has had and continues to have a solid career.

In 2018 Dave Dombrowski did not make a deadline deal to invigorate the bullpen but he did get a piece that is still part of the picture today. Right-hander Nathan Eovaldi became available via Tampa and Boston pounced. Eovaldi made 12 mound appearances (11 starts) and enough to get Boston some needed innings in the rotation.

Eovaldi then put forth a solid playoff run and a World Series loss that was a dramatic relief appearance. That catapulted Eovaldi into a questionable four-year contract that this season is showing its value. The player Boston sent Tampa – Jalen Beeks – has also been a solid performer for the Rays. A deal that helped both teams.

Dombrowski would also pick up Steve Pearce from the Blue Jays ahead of 2018’s deadline in a deal that paid off big for the Red Sox. Pearce would become a monster in AC’s lineup and would quickly become a Yankee killer whenever the two teams faced. The veteran played such a massive role with the club that he would earn World Series MVP honors as well as a new contract. Unfortunately, injuries would severely derail his time with Boston after ’18 and he would eventually retire.

Sometimes it does fail. The Red Sox in 1988 needed – no surprise – pitching. The O’s dealt right-hander Mike Boddicker to Boston for prospect Curt Schilling and outfielder Brady Anderson. Boddicker was solid (7-3, 2.63) as expected. Unfortunately, it was not enough. Boston won the American League East and was executed 4-0 by the A’s.

Schilling did little for Baltimore and Anderson went on to have a fine career with the O’s. Anderson made three All-Star teams and hit a questionable 50 home runs in 1996. Schilling as just about any baseball fan knows eventually returned to Boston and the curse-breaking of 2004.

Deadline teams may not have immediate returns and one of the most notable happened in 1997. The Red Sox were sellers that season and Seattle were buyers. Boston had just what the M’s needed in right-handed closer Heathcliff Slocumb. The M’s had two youthful prospects – Jason Varitek and Derek Lowe. And we know how that turned out. And the M’s lost in the playoffs.

The Red Sox will certainly not be sellers, but to just what extent will they buy? Are they willing to strip the farm system? Carry payroll? Trade an MLB piece? Tampa Bay needed another bat and did not hesitate in getting Nelson Cruz. Expect the Buffalo – soon-to-be Toronto – Blue Jays to add needed pitching. New York could sell or buy.

The Red Sox could do absolutely nothing. Chris Sale will be back and apparently, has passed all his arm tests. That would be similar to having a top-tier starter arrive via trade. Manager Alex Cora is doing some considerable managerial mix and match with his ever-evolving roster. Boston’s farm system is inching up in the rankings department. The payroll and the ever ominous Luxury Tax are being stabilized. Boston could just go with it and do waiver wire shopping.