Red Sox took the wrong road by not signing Jon Lester

The Boston Red Sox made an error. It was not on the field, but in the management suite. They should have kept Jon Lester, saved money, and have had more mound consistency.

On Tuesday two left-handers with a Boston connection pitched. One walked away with a win and the other – despite a nice performance – picked up a loss.

When you have a sure thing why look elsewhere? The Red Sox had exactly that with lefty Jon Lester, a rare successful pitcher from their own farm system. Lester did everything one would expect of a top of the rotation starter.

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Jon Lester is unusual in the baseball of today in his physical consistently. He is on a streak of ten straight seasons of 30+ starts. In six of Lester’s full seasons in Boston the innings pitched exceeded 200+ innings. The lefty brings consistency with durability and excellent performance. Lester went to Oakland in a trade with 110 wins in his Boston career – a .636 winning percentage, three World Series wins, and a 6-4 playoff record.

Boston management made an offer that was not even remotely close to market value. Was it a negotiation ploy? Did they expect an excessive hometown discount? Did they simply view the risk of a 30-year-old or a potential boatload of injuries too much of a risk? The Red Sox smartly avoided an older and injury prone Pedro Martinez. Was the assumption that Lester would follow a similar track? All are unknowns.

The Boston Red Sox became acutely aware of management errors in not procuring the services of a pitcher who would be comfortably designated an “Ace” based on performance. The Red Sox judiciously corrected their history and went shopping. The result was David Price for $217 MM – far more than the $155 MM that Lester received from the Chicago Cubs.

Price has not been a failure, but a disappointment. Injuries, personal issues with the media, an inconsistency of performance results and not being the “Ace” expected. Price – also a lefty – is a year younger, so the age question is not practical in avoiding Lester. Neither is wear and tear since Price also was a pitching workhorse. Price would and should be viewed at the time as an expensive, but solid acquisition.

The David Price that now takes the mound is a middle and possible a top of the rotation pitcher. If Price was being paid $15 MM his performance would be acceptable and expected. If he was stepping up his postseason game the dollars spent would be more palatable to Red Sox Nation. So far, that is not the case.

The Red Sox made a mistake and a costly one. Price is certainly not in the failure category of Pablo Sandoval or Hanley Ramirez, but the impact is felt. Would they still have traded for Chris Sale if Price was the Price of his Tampa Bay salad days?

Pointing the finger at management failure is easy, but this is one where I would have taken the sure thing. And that was Lester. The Red Sox still had the financial resources to sign Price and may have. My critique is most certainly limited since at the time the Price signing appeared to be a makeup call. Did anyone expect Prices’ deterioration? I didn’t – my only issue was the extra $60 MM that could have gone elsewhere. That extra money has made a looming specter of the 42.5% luxury tax a possibility.

Lester’s departure, and to a lesser extent Andrew Miller, had repercussions. I would have taken a legitimate shot at both when they became free agents. The departure set off a domino effect for other signings and trades that could have been avoided.

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Hindsight is a great tool and hindsight shows the Red Sox simply blew it with Lester. David Price will continue to be a good pitcher and Lester will continue to give 200+ quality innings for the Cubs and not the Red Sox.

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