Red Sox History: Bold trades of prospects are needed to bolster pitching

2023 Red Sox Winter Weekend
2023 Red Sox Winter Weekend / Billie Weiss/Boston Red Sox/GettyImages

The Boston Red Sox farm system is supposed to be churning out viable prospects, and MLB currently has assigned the Sox to 16th place on the rankings. I have seen other sites where it is third, so each has its criteria, but Boston's is improving.

The prospect locker is looking upwards, with Marcelo Mayer, Kyle Teel, Ceddanne Rafaela, Roman Anthony, and others restricted to position players. In Kindergarten, you are taught to share your toys, and it is time for sharing to fortify desperately needed pitching.

Prospects can be used as replacements for departed players, avoiding costly contracts at least short term, but they are also valuable trading chips. Dealing with a potential star to fill a roster hole can have detrimental consequences, and Jeff Bagwell's name can explain that approach's pitfalls.

The first of Chaim Bloom's draft picks and international signings have yet to arrive, but those of departed president of baseball operations Dave Dombroski are making an impact. Triston Casas, Jarren Duran, Brayan Bello, and now Ceddanne Rafaela, which means potential trade candidates. Bloom could also avoid sharing by dipping into the free agent pool for pitching, and by pitching, that does not mean the usual flotsam and jetsom Bloom has signed in the past.

The Red Sox have wandered down that road in the past, and in this century of team success, they have done it three notable times. The first was in 2003 when Theo Epstein (remember him?) traded three top prospects, including number one prospect Jorge De La Rosa, Brandon Lyon, and Casey Fossum, to the Diamondbacks for Curt Schilling. Theo got a world of heat for this move, especially regarding Fossum. Schilling was 37 years old and coming off an 8-9 season.

The 'Backs soon flipped De La Rosa, who had a 15-year MLB career that resulted in 104 wins. Righty Lyon was 4-6 for the 2003 Red Sox with nine saves. The conclusion by most is Lyon would be a quality bullpen arm, and that did not happen. Fossum was a 25-year-old lefty and a minor disappointment after three seasons in Boston. Fossum did nothing (4-15, 6.65) for Arizona; his career never panned out.

Is a trade of prospects the way to go for Red Sox to get pitching?

Then there is Schilling, who twice posted 20+ wins with Arizona. The righty went out to win 21 for the 2004 Red Sox, and we all know the rest of that history. Oh man, did Theo split RSN on this deal.

The next prospect-enriched deal was in 2005 when two high-profile prospects - Hanley Ramírez and Anibal Sánchez, were traded to Miami. Boston was (surprise!) once again in the market for pitching, not just any pitching but stud pitching.

Ramírez was a five-tool player with extraordinary talent who became the Rookie of the Year in 2006 and won a batting title in 2006. Ramírez parlayed his statistics into several substantial contracts, including a return to Boston.

Sánchez never quite attained the promised pitching land but had a respectable 16-year MLB career. If Boston had kept them, they would not have received Josh Beckett and Mike Lowell; both became instrumental in the 2007 championship season. In the 2007 playoffs, Beckett went 4-0 and became the ALCS MVP.

If you like Justin Turner, you would have loved Lowell. In that 2007 season, Lowell was a run-producing machine with 120 RBI and 21 home runs. Toss in a glue glove at third base and a World Series MVP.

The unknown is the consequences for Boston if they keep both young players. The known is clear, and that is a WC championship. The trade was a foolish or bold move but it obviously worked rather well for Boston despite losing prospects.

Michael Kopech and Yoán Moncada were among the Red Sox's most highly touted prospects, with Moncada being occasionally ranked the best in baseball on several evaluation sites. Moncada was a costly signing for Boston, but his possible ceiling was worth the risk.

With his physical presence and blazing heater, Kopech was a first-round pick and considered a possible Roger Clemens. Kopech also developed a negative reputation in the farm system, raising issues regarding his future. Pushing the negative aside, Kopech had a "Can't miss" label on his resume.

The Red Sox traded both to the Chicago White Sox for Chris Sale. Sale was arguably the best pitcher in baseball and showed that his first two seasons in Boston. In Sale's third season, the arm-wearing down showed, yet Sale managed a 12-4, 2.12 record, and we all remember Manny Machado swinging away fruitlessly for the last out in the WS. Then Sale fell apart.

Moncada showed enough with the White Sox to get an enormous contract and went downhill. Injuries and poor performance have scuttled Moncada and now Kopech. Kopech - like Sale - had Tommy John Surgery, and his overall performance has undoubtedly not rekindled memories of Clemens. Boston got their championship, and Sale already had an extension that is a contractual nightmare. Kopech and Moncada are fast looming as what could have been players.

The Red Sox now have trading chips of talented players with a potentially high plateau and controllable. The need is apparent, and that is pitching. The farm system is not exactly a buffet of quality arms, with Bello being a rare find in an otherwise bleak landscape of pitching prospects.

Do the Red Sox make the bold moves they have in the past? The previously mentioned deals, the results are known -- they succeeded. The unknown is that without those moves, would they still have all those titles?