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Alex Speier

In the end, John Lackey lived up to his contract

Once teammates with the Red Sox, John Lackey and Jon Lester will face off in the Game 1 of the NLDS between the St. Louis Cardinals and Chicago Cubs.Bill Greene/Globe Staff file/Boston Globe

While the Red Sox’ memories of 2013 receded with startling rapidity, Friday evening will offer a sort of back-to-the-future opportunity to remember that unlikely run.

The Red Sox’ two pitching anchors of that October, Jon Lester and John Lackey – the only starting pitchers to claim wins for the Red Sox in that postseason run, with Lester accumulating four W’s and Lackey collecting three – will both take the mound in the postseason. But this time, the close friends who spent nearly five years as teammates with the Red Sox will take the ball as opposing Game 1 starters, with Lester’s Cubs facing Lackey’s Cardinals.


It’s natural to focus on the what-could-have been scenarios for the Red Sox with both. Had the Sox extended Lester in the spring of 2014, there’s no question he would have been the team’s Opening Day starter and unquestioned leader, affording a measure of order that seemed absent early in the year.

Had the Sox retained Lackey this year on his major league minimum salary, rather than trading him to the Cardinals at the 2014 trade deadline, he likewise would have offered the Sox not just a veteran presence to lead the rotation along with a pitcher who defied age to post a career-best 2.77 ERA while delivering 218 innings.

Yet the idea of how different the 2015 Sox season might have been with either pitcher is a matter of conjecture. Moreover, even now, it’s premature to reach a definitive verdict about the trades that the Red Sox made involving the two pitchers, given the to-be-determined impacts of Joe Kelly (acquired with Allen Craig for Lackey) and Rick Porcello (the eventual return for Lester). It will be at least another year and perhaps several before those deals can be assessed with complete information. But there’s a topic whose dimensions are now more clearly defined that offers its own considerable level of interest.


For years, Lackey’s contract was slammed as yet another sign of the folly of long-term, big-money deals for pitchers. His five-year, $82.5 million deal was viewed as nothing short of a disaster for most of Lackey’s first three years in Boston (especially 2011 and the 2012 season he lost to Tommy John surgery), even with his lost season tacking an extra year onto his deal at the major league minimum.

But over the final three years of Lackey’s contract, he reversed that interpretation. He and Lester drove the rotation bus in October 2013, and Lackey performed at the level of anything from a No. 1 to No. 3 starter over the final three seasons of his contract – with his role as a rotation anchor earning him the first start of the Cardinals’ postseason run. And so, in the end, it doesn’t seem unreasonable to say that Lackey lived up to his deal, which is now at its end.

Over the eventual six-year term of his contract, Lackey’s overall performance was more modest than spectacular. For about $83 million over six years, he went 63-56 with a 4.08 ERA while making 28 or more starts five times. His overall performance, in the calculations of Baseball-Reference.com, was worth 9.3 Wins Above Replacement – or about 1.6 WAR per year at an eventual cost of $8.9 million per win.

That’s not a cheap rate but it’s also not a disaster. Indeed, of the 14 deals of five-plus years that free agents have signed since Kevin Brown became the Neil Armstrong of pitching contracts with his seven-year, $105 million landmark after the 1998 season, Lackey’s performance falls into a fairly well-defined middle of the pack.


Were they worth it?
Completed contracts of starters who signed free-agent deals of 5-plus years, 1998-2015
Team Seasons Years Total $ AAV WAR WAR/year $ (M) per win
Mike Mussina Yankees 2001-06 6 88.5 14.75 28.9 4.8 3.1
Cliff Lee Phillies 2011-15 5 120 24 21.2 4.2 5.7
Kevin Brown Dodgers 1999-2005 7 105 15 22.9 3.3 4.6
CC Sabathia Yankees 2009-15 7* 161 23 22.6 3.2 7.1
Gil Meche Royals 2007-11 5*** 55 11 10.3 2.1 5.3
A.J. Burnett Blue Jays 2006-10 5** 55 11 10.3 2.1 5.3
Kevin Millwood Rangers 2006-10 5 60 12 8.8 1.8 6.8
A.J. Burnett Yankees 2009-13 5 82.5 16.5 8.4 1.7 9.8
John Lackey Red Sox 2010-15 6 83 13.83 9.3 1.6 8.9
Barry Zito Giants 2007-13 7 126 18 3 0.4 42.0
Mike Hampton Rockies 2001-08 8 121 15.1 2.9 0.4 41.7
Denny Neagle Rockies 2001-05 5 51.5 10.3 1.3 0.3 39.6
Darren Dreifort Dodgers 2001-05 5 55 11 0.2 0.0 275.0
Chan-Ho Park Rangers 2002-06 5 65 13 0.2 0.0 325.0
* - Numbers include all seven years under original deal; however, Sabathia negotiated an extension after the 2011 season rather than opting out after three seasons.
** - Numbers include all five years under original deal; however, Burnett opted out after three years and signed with the Yankees as a free agent
*** - Meche retired before the fifth and final season of the contract, at a time when he couldn't pitch.
SOURCE: baseball-reference.com; MLB Trade Rumors transaction tracker

At the top of the heap, there are four pitchers whose long-term deals netted performers who averaged at least 3.0 WAR per year, with Mike Mussina and Cliff Lee leading a pack joined by CC Sabathia and Brown. (Note: All seven years of Sabathia’s original contract with the Yankees, which ran from 2009-15, are examined, though it’s worth noting that Sabathia and the Yankees renegotiated the final four years of the original deal and added a fifth after the 2011 season, when he had the right to opt out.)

Lackey then belongs to the next cluster of pitchers who performed, on average over the life of the deal, as something along the lines of a mid-rotation (No. 3 or No. 4) starter. He joined A.J. Burnett (who opted out of one deal that would have placed him in this group and then signed another), Gil Meche, and Kevin Millwood in producing around 1.5-2.0 wins per year.

Finally, there is the Big Five of free agent pitching catastrophes: Barry Zito, Mike Hampton, Darren Dreifort, Denny Neagle, and Chan-Ho Park, all of whom signed monster contracts and delivered performances that were barely distinguishable from that of a replacement-level pitcher over the life of their deals.


Unquestionably, the overall results of deals of five-plus years for pitchers suggest the possibility for enormous risk. Yet the history of these 14 completed deals also suggests that the returns have not been as singularly awful as one might assume, and that many of them have offered something between solid and excellent returns.

Cardinals GM John Mozeliak tells Benjamin Hochman of the St. Louis Post-Dispatch that Lackey’s big-game presence was part of his motivation for acquiring the righthander from the Red Sox in 2014.

Patrick Mooney of CSN Chicago writes that this setting is why the Cubs signed Lester.

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