Whatever sting the Boston Red Sox felt in watching Jacoby Ellsbury sign a seven-year, $153 million contract with the New York Yankees before the 2014 season almost certainly has subsided, likely replaced by both a sense of relief and a deep appreciation for what’s since come to light.

The Yankees (finally) released Ellsbury on Wednesday, eating more than $26 million ($21.1 million in salary for 2020 and a $5 million buyout for 2021) in the process, and one can’t help but view the move through the lens of the Red Sox, the organization with which the outfielder spent his first seven seasons. To say the Red Sox dodged a bullet by not splurging for an Ellsbury extension on the heels of their improbable 2013 World Series win would be an understatement, especially considering the subsequent success of Boston’s outfielders, namely Mookie Betts.

Ellsbury’s tenure with the Yankees was an unmitigated disaster, with injuries and underperformance turning his hefty price tag into a colossal blemish in New York’s typically oversized payroll. He averaged just 130 games, 10 home runs, 50 RBIs, 26 stolen bases and a .264/.330/.386 slash line in four mostly underwhelming seasons from 2014 through 2017 and hasn’t played since thanks to various ailments.

Ellsbury’s 8.0 WAR since the beginning of 2014, according to FanGraphs, ranks 67th among qualified Major League Baseball outfielders — right between Leonys Martin (8.2), an elite defender with no bat, and Gregory Polanco (7.9), a decent-but-not-great outfielder who’s also been beset by injuries. For context, Betts has posted a 37.2 WAR in that span — second only to Mike Trout (52.5), the best baseball player on the planet — with two single seasons (2016; 8.3 and 2018; 10.4) surpassing the 8.0 mark Ellsbury posted across 520 games.

Jackie Bradley Jr., who ultimately became Ellsbury’s successor as Boston’s center fielder, ranks 29th (13.7) in that stretch, while current Red Sox left fielder Andrew Benintendi ranks 58th (9.0) despite playing in 49 fewer games than Ellsbury and not even being arbitration eligible until this offseason.

It’s safe to say the Red Sox have received much more bang for their buck over the past six seasons, a fact magnified by the salaries (per Baseball Reference) earned by Boston’s current outfielders (Betts, Bradley and Benintendi) relative to Ellsbury since the latter’s departure.

Mookie Betts (2014-19): $32.5 million (37.2 WAR)
Jackie Bradley Jr. (2013-19): $20.3 million (13.5 WAR)
Andrew Benintendi (2017-19): $1.9 million (9.0 WAR)
Combined salary/WAR: $54.7 million (59.7 WAR)

Jacoby Ellsbury (2014-19): $126.6 million (8.0 WAR)

…The Betts-Bradley-Benintendi trio has posted 51.7 more WAR than Ellsbury at a fraction of the cost ($71.9 million less).

The Red Sox have received an MLB-best 67.1 WAR from all of their outfielders since the beginning of the 2015 season, Betts’ first full campaign. The Yankees, to their credit, haven’t lagged too far behind in that department (60.2 WAR; fourth-best) and have done an admirable job of overcoming Ellsbury’s albatross of a contract, earning four playoff berths, including a division title, since the 2011 American League MVP runner-up decided to don pinstripes.

But Ellsbury’s tumultuous tenure with the Yankees — as well as the simultaneous success enjoyed by Betts and the Red Sox’s other outfielders — is a cautionary tale for throwing money at big-name free agents, even those who seemingly are known quantities based on spending nearly a decade with the organization. It’s also evidence of the important role that scouting and development play in helping teams prepare for and ultimately overcome notable departures.

Of course, not every situation is the same. So, to suggest the Red Sox shouldn’t pay Betts, a free agent after the 2020 season, solely because Ellsbury — and many other free agents, for the matter — flopped elsewhere would require a reckless disregard of several key factors. Betts, at age 27, has been a far better player than Ellsbury was prior to reaching free agency in 2013 at age 30.

Still, this represents an interesting exercise in evaluating risk versus reward. The Yankees took a significant risk in doling out big bucks to Ellsbury, only to watch as the Red Sox reaped the real rewards that came with their restraint in letting a disposable, albeit high-profile asset walk away.

Thumbnail photo via Noah K. Murray/USA TODAY Sports Images