Truth be told, I’m stealing this “What if” idea from The Athletic, whose various writers are ‘exploring what might have happened if things had gone differently at significant points in sports history.’
The Athletic’s Chad Jennings began by looking back as recently as the Mookie Betts and David Price trade, and in accordance with that, I thought it would be interesting to look back at a time in Red Sox history prior to the club signing Price to a then record-setting seven year, $217 million contract in December 2015.
Yes, this point in time was just a few months before that, in October to be more specific.
The Red Sox were coming off their second consecutive last place finish in the American League East, marking the first time they had done that since the 1929-1930 seasons.
Under new president of baseball operations Dave Dombrowski, who was hired to replace Ben Cherington that August, the club was in desperate need of front-line starting pitching help coming off a 2015 campaign in which they ranked 13th in the American League in starters’ ERA (4.34).
According to The Boston Globe’s Alex Speier, before Dombrowski had even been hired, the former Tigers executive identified soon-to-be free agent left-hander David Price as a potential target to pursue that winter in an interview with Red Sox brass.
Potential trades for names such as the White Sox’ Chris Sale, the Indians’ Corey Kluber, and the Athletics’ Sonny Gray seemed possible as well.
Come October, per Speier, “the Red Sox tried to quantitatively compare the cost of a trade for an ace versus signing one in free agency. [Director of major league operations Zack] Scott oversaw the production of a sixteen-page memo, in this case exploring a hypothetical deal for the A’s Gray, in exchange for a five-prospect package of Rafael Devers, Blake Swihart, Manuel Margot, Henry Owens, and Javy Guerra.”
Based on the projections used in this memo, “the Red Sox considered such a trade a $230 million proposition, with the prospects carrying a projected future worth of $200 million on top of the roughly $30 million that the team anticipated it would have to pay Gray in salary over his remaining four years of team control.”
Gray, at the time, was entering his final year of being a pre-arbitration player.
The results of the assessment, however, did not sway the Sox to swing a trade for an ace, as they “believed it would cost less simply to sign a free-agent starter than it would to trade for a rotation solution.” That was especially the case in the event that including Mookie Betts or Xander Bogaerts in a trade for a starting pitcher became a must for another team, like the A’s.
In the end, Dombrowski and Co. chose giving up money over giving up prospects and wound up signing Price to that then-record-setting seven-year deal that December.
Although it does not appear that the Red Sox were all that close to acquiring Gray from Oakland, it is fascinating to look back and wonder what could have been.
Out of those five prospects listed above, Devers would be the one missed the most, as the major-league careers of Swihart, Margot, Owens, and Guerra haven’t really panned out to this point for various reasons.
It’s also compelling to look back because Gray in Boston would have been no sure thing. That much was made evident by a rather tumultuous 1 1/2 year tenure with the Yankees, although he has since bounced back nicely after being traded to the Reds in January 2019.
Price’s tenure with the Red Sox wasn’t picture-perfect either, but he did play an integral role in the club’s march to a historic World Series title in 2018 before getting traded to the Dodgers last month.
All in all, handing out massively lucrative contracts and involving top prospects in blockbuster trades both involve a great deal of risk. In the case of acquiring the services of a front-line starter when they most desperately needed one in Dombrowski’s first offseason as president of baseball operations, the Red Sox went with the former over the latter.
Note: If you haven’t already, you should read Homegrown by The Boston Globe’s Alex Speier. This piece would not have been possible had it not been for the information provided in that terrific book about how the Red Sox built a World Series champion from the ground up.