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Which would pay off more for the Red Sox: pursuing an elite free agent, or holding on to a high draft pick?

George Springer has played seven seasons for the Astros.Gregory Bull/Associated Press

Should a second-round draft pick represent an impediment to signing any of the elite free agents on the market? Should the No. 39 pick in next year’s draft really deter the Red Sox from making a run at center fielder George Springer, righthander Trevor Bauer, and second baseman DJ LeMahieu when all three would address areas of glaring need for a last-place team?

The question looms as the Red Sox consider how to upgrade for 2021. On one hand, the Red Sox are trying to regain their footing in a division with the reigning pennant winner (Tampa Bay), the team with the second-best winning percentage in the American League the last four years (Yankees), and an up-and-comer looking to make an offseason splash (Toronto).


At the same time, the team is trying to replenish for the long haul, seeking to create a critical mass of dynamic young talents. A draft pick who turns into an ascendant big-league regular or star can impact a team for at least five to seven years. Signing Springer (31 years old), Bauer (turning 30 next month), or LeMahieu (32) would secure the services of a player likely to excel early in the life of a deal but whose performance would inevitably decline.

Still, there’s value in the short term. Bauer is an ace coming off a Cy Young Award. Springer ranks among the top 15 players in Wins Above Replacement the last five years, according to both Fangraphs and Baseball Reference. Red Sox second basemen last year hit .220/.273/.313; LeMahieu led all second basemen in average (.364), on-base (.421), and slugging (.590).

The Red Sox haven’t ruled out the idea of signing a player who received (and rejected) a one-year, $18.9 million qualifying offer from their 2020 clubs — even at the cost of their second-round pick. Teams that sign a free agent who received a qualifying offer — Springer, Bauer, LeMahieu, and catcher J.T. Realmuto this year — to a deal of at least $50 million must give up a draft pick. The penalty varies by market size.


Signing a player like DJ LeMahieu could cost a team a draft pick.Sean M. Haffey/Getty

But team officials privately concede that such a move is unlikely. Usually, those all-in signings or trades, particularly for players in their 30s, are pursued by playoff-caliber teams trying to upgrade to advance their title hopes. The Sox are a tier below that, trying to reestablish themselves as playoff-worthy.

At least part of the team’s reluctance to chase the biggest free agent names relates to the value the team puts on its second-round pick — as of now, the 39th overall. While there are plenty of busts from that area of the draft, the hits include some of the most dominant players in modern baseball history.

Barry Bonds was taken out of high school by the Giants with the No. 39 pick of the 1982 draft. (He didn’t sign, and three years later was drafted No. 6 overall.) Among those who did sign after being taken 39th: Don Baylor (1967), and recent All-Stars Lance Lynn (2008) and Joey Gallo (2012). The Red Sox have done well in that area of the draft, taking Jackie Bradley Jr. at No. 40, Fred Lynn at No. 41, and Clay Buchholz at No. 42.

A pair of second-round selections in 2002 (Jon Lester, No. 57 overall) and 2004 (Dustin Pedroia, No. 65) helped lay the groundwork for the Red Sox’ titles in 2007 and 2013. LeMahieu himself was a second-rounder (No. 79, 2009).


“All draft picks are calculated risks to some extent. There’s no guarantees with any of them,” said Red Sox chief baseball officer Chaim Bloom. “You can look at 2002 or 2004 to see just how valuable a second-round pick can be in this organization. It’s really valuable.”

At the same time, teams must remain clear-eyed about the actual likely impact of such a pick. It changes a franchise to draft a Lester or Pedroia in the second round, both because of the contributions such players make and their relatively low cost permits the team to spend on other parts of the roster.

Even so, typically, only one or two players from the second round each year goes on to have such a career. The second round of the draft this year encompasses picks 36 through 64. In the 56-year history of the draft, fewer than half (43.2 percent) of players taken in that range have reached the big leagues.

According to the calculations of Baseball Reference, about one of every 13 (7.5 percent) players taken in that pick range has been worth as many as 10 Wins Above Replacement — a baseline for players who emerged as solid, longtime regulars. About one out of every 34 (3 percent) has produced 25 WAR, often indicative of star-caliber performance.

What's the value of a draft pick? In evaluating the draft since its inception in 1965, how do players picked within the first three rounds pan out? We looked at three categories — making the majors, achieving a career WAR of plus-25, and achieving a career WAR of plus-10 — to see what percentage of players accomplished each.
Round Reached big leagues Had career WAR of +25 wins Had career WAR of +10 wins
1st round (Picks 1-29) 65.5% 8.6% 19.8%
Comp round A (Picks 30-35) 50.3% 3.0% 8.6%
2nd round (Picks 36-64) 43.2% 3.0% 7.5%
Comp round B (Picks 65-72) 38.4% 3.3% 7.1%
3rd round (Picks 73-102) 33.8% 1.8% 4.7%
SOURCE: Baseball Reference

The odds of landing a difference maker are somewhat higher where the Red Sox are likely to pick. In the Nos. 36-40 spots, 45 percent of draftees have reached the majors, with 10 percent having accumulated at least 10 WAR and 4.3 percent (about one in every 23) delivering 25.


The pick also would give the Red Sox about $2 million to spend in their draft budget. Money that the team could apply not just on a second-rounder, but also to picks further down in the draft in an attempt to increase the odds of adding a legitimate prospect in later rounds.

This year, for instance, the Sox didn’t have a second-round pick due to MLB penalties following the investigation into the illegal use of video to decipher sign sequences in 2018. As a result, the team took a player it might have been able to grab in the second round — Nick Yorke — in the first round.

“We had to navigate the draft very differently than we might have if we had the pick in that round,” Bloom said.

Is that draft-pick value enough to prevent a team from signing a free agent whom it believes could push it over the top in pursuit of a title? Almost certainly not.

But for a team that is still trying to lay the foundation for a multiyear title run, a top-40 draft pick represents a lottery ticket with enough potential value to at least represent part of the decision.

“It obviously has value. It gives you a very good shot at an impactful player,” said Bloom. “You just have to factor that in [regarding potential free agent signings]. It’s not an absolute one way or another, but you can’t be blind to the value that you would be giving up in that scenario.”


Alex Speier can be reached at alex.speier@globe.com. Follow him on Twitter at @alexspeier.