It is nearing the end of Year One, still too early to draw conclusions about the ultimate merits of the five-year deal that John Lackey signed with the Red Sox. After all, Josh Beckett seemed like a bust in his first year in Boston in 2006; one year later, when he and Mike Lowell led the Sox to a title, the decision to acquire those two players looked very different.
That said, it is long past the time when it can be argued that Lackey’s first season in Boston represents anything but a disappointment. And the odds are very much stacked against the Sox getting what they paid for when they inked the big right-hander to a five-year, $82.5 million contract last December.
On Friday, Lackey added to the pile of evidence suggesting this is one of the worst years of his career. The Blue Jays beat him early and often, collecting eight hits and seven runs (six earned) in 4 1/3 innings against him as the Sox lost, 11-9. (Recap.)
“You deserve to lose when you pitch like this,” Lackey (12-11, 4.63 ERA) conceded after the game. “It is what it is. I didn’t pitch well and didn’t give us a chance to win.”
That has been a surprisingly frequent refrain for Lackey in his first year in Boston. The Red Sox are now 14-16 in games in which Lackey has been their starter. He has now allowed five or more earned runs in 10 of his 30 starts this year, the most such outings he’s had in any of his nine big-league seasons. His 4.63 ERA would be his worst since 2004.
Even acknowledging that Lackey has been a staff horse, remaining healthy enough to lead the Sox in innings and matching Jon Lester for the most quality starts on the club, the question is no longer about the merits of Lackey’s first year in Boston. The question is about what the former Angels ace will be able to deliver over the remainder of his deal from 2011-14.
But, of course, the Sox knew that long before they signed Lackey to the largest contract (in average annual value) that they’ve ever given to a pitcher. The odds are weighted incredibly against the likelihood of a free-agent pitcher ever delivering on the value of his deal, something the Sox are well aware of.
After the 2008 offseason, Sox GM Theo Epstein said the following when peering across a free-agent landscape that included CC Sabathia, A.J. Burnett, Derek Lowe and Oliver Perez, among others.
“There aren’t too many top free-agent pitchers who end up being worth their contracts,” said Epstein. “Adding big-name starting pitching through free agency always sounds great on paper. … But the reality is that those deals often don’t work out for the club. It just can be a risky transaction on day one, let alone looking back at it after the fact.”
Yet one year later, the Sox decided to make the bold move to engage in what they acknowledged to be the risky business of a long-term commitment to a free-agent pitcher.
“When you enter into free agency from the team side, you want to try and manage the commitments as best you can and obviously you always want shorter deals, you always try to get the best deal you can for your club,” Epstein explained at the press conference to announce the signing of Lackey. “John’s someone, with his track record and his consistency, who has put himself in a position to deserve a contract like this.
“If you look at recent signings and last year’s free agent pitching signings for example, certainly John ranks right up there with those guys who got similar contracts if not exceeds them. It’s something we had to think long and hard about but in the end we believe in John, we believe in our pitching and our starting pitching going forward that this puts us in the best position.”
Now, for the Sox, the most disturbing part of Lackey’s performance this year is not that it has represented a dramatic departure from his career norms, but instead that it has followed a familiar pattern of free-agent pitchers, in which players get rewarded for past performance rather than what they are likely to accomplish during the life of a deal.
Lackey is now one of 15 starting pitchers since 2000 to receive a free-agent deal worth at least $50 million. He is part of a pattern in which those hurlers have been notably worse in the first year of their new deals than they were in the last season of their old ones.
As a group, those pitchers averaged a 14-10 record, 215 innings and a 3.67 ERA in their final year before their landmark free-agent deals. In the first year of their new deals, they averaged a 13-10 record, 190 innings and a 4.32 ERA.
Of the 15 pitchers, Lackey will become the 11th with an ERA that is at least half a run worse in the first year of his new deal than it was in the final year of his old one. More often than not, big-money free-agent pitchers have come up short in their inaugural seasons of their new deals. Lackey’s struggles represent the norm, rather than the exception.
Yet for the Sox, that first-year pattern is not nearly as alarming as what typically follows it. After all, as a group, those 15 free-agent pitchers have at least been largely healthy in the first season of their shiny, big new contracts.
The real risk comes in the later seasons of their multi-year deals. That is when age typically starts to catch up with the pitchers. Arms, shoulders and legs begin to break down under the accumulated stress of a career spent working in a job that would have been declared an abomination of nature in the Middle Ages, with its practitioners thrown into rivers to see if they could float.
All of the 15 free-agent contracts of at least $50 million had a duration of at least four seasons. Thus far, if one views 2010 as being (for practical purposes) concluded, the picture of what teams get from their massive commitments to free-agent pitchers is fairly gruesome.

• An average season from that group of pitchers reveals a 9-8 record and 4.43 ERA in 142 innings.
• Including 2010, there have now been 60 seasons of work from the pitchers who made $50 million or more in free agency.
• Of those, exactly half (30) have resulted in at least 30 starts (or, in the case of 2010, 28 or more starts with a likelihood of reaching the 30-start total).
• The group tends to be healthy in year one of contracts, with 12 of the 15 pitchers (80 percent) reaching the 30-start milestone. But from that point on, the ability of pitchers to reach that marker starts to drop significantly:
  
  Year 1: 12/15 (80 percent)
  Year 2: 9/14 (64 percent)
  Year 3: 4/11 (36 percent)
  Year 4: 2/10 (20 percent)
  Year 5: 2/6 (33 percent)
  Year 6: 1/2 (50 percent)
  Year 7: 0/1 (0 percent)
  Year 8: 0/1 (0 percent)

In that context, the biggest issue for the Sox with the Lackey contract may not have even come yet. He has, at least, been healthy. And there is a good chance that he will be healthy again in Year Two, thus creating the possibility of a bounceback.
It's worth noting that Bartolo Colon went 18-12 with an unsightly 5.01 ERA as a 31-year-old in the first season of his four-year deal with the Angels; the next season, he went 21-8 with a 3.48 mark and won the Cy Young.
But Colon only made 29 total starts over the final two years of his contract. So, for their $51 million, the Angels enjoyed a sub-standard first year, and outstanding second year, and virtually nothing in the final two years.
Again, it is premature to say what kind of return the Sox will receive from Lackey over the life of his five-year deal. That said, his first year in Boston suggests a familiar pattern with ominous overtones.

The Sox recognized they were taking on risk when committing to Lackey for five years. But they plunged ahead, hoping that the reward would exceed the risk. That has not been the case in 2010. Whether Lackey is capable of bucking the historical trendlines to reverse that initial assessment remains to be seen.