Bradford: Did Red Sox learn their lesson after Jon Lester mess-up?

Rob Bradford
February 18, 2019 - 8:21 pm

FORT MYERS, Fla. -- Oh, by the way, the Red Sox blew it five years ago.

That was the out-of-nowhere admission by principal owner John Henry Monday. It came and went in the midst of the 22-minute get-together with the team's ownership with nary a warning and very little follow-up. Yet the proclamation made by Henry was something that was a long time in coming.

"I think we blew the Jon Lester -- we blew that signing in spring training," Henry said. "So for reasons that are pretty apparent now, which I won't go into, but they're apparent. But it wasn't... you can see what's gone on in free agency. The price of WAR has gone up radically (enough) that it's difficult whether it's a pitcher or a position player entering into a really long term contract with high dollars. And we haven't had a great track record. We've done better with pitchers perhaps than we have with hitters and really long-term contracts."

While so much has happened since Lester left town midway through the 2014 season, the importance of acknowledging what an enormous misstep his negotiations were shouldn't be understated. Was it the biggest mistake of this ownership's 18-year tenure? It's right up there. And that's why zeroing in on what went down five years later is absolutely fair game.

In case you forgot ...

Lester wanted to stay with the Red Sox. He was a creature of habit who felt comfortable performing in the only organization he only knew. He would later tell WEEI that if the Red Sox offered him in the vicinity of a five-year, $120 million deal before the start of the 2014 season -- his contract year -- that would have got the job done. Instead, the Red Sox took the same approach they had during previous negotiations -- start obscenely low. In this case that was at four years, $70 million.

Word got out early on in that 2014 season what Lester was being offered. It was a leak spawned by the pitcher's teammates who were offended the guy who had anchored the 2013 World Series-winning starting staff was being lowballed in such a manner. The Red Sox then responded by issuing murmurs that the pitcher's camp wasn't even giving a counter-offer when in fact the reason for no contractual rebuttal was due to where the Sox had put the starting point. From Lester's side of things, there was a feeling that any response was going to have to be uncomfortably high in order to find a palatable middle ground. And if such a number was put on the table then there would be a likelihood of another leak, unfairly painting the pitcher as greedy.

Again, all Lester wanted to do was stay in Boston.

Because in large part of where things started in spring training the negotiations remained in a stalemate all the way up until the lefty was shipped to Oakland just before the non-waiver trade deadline. 

While so many might focus on the Red Sox not matching the Cubs' offer of six years and $155 million (with a mutual option for $25 million in 2021), it was the swing and miss in spring training that truly put life without Lester in the spotlight. If the Sox just broke free from their blueprint and understood that this should have been a turn-key process, life would have undoubtedly been hugely different.

Due to Lester's treatment, John Lackey asked to be traded, which he was. If the two of those starters stuck around (with Lackey playing at the major-league minimum in 2015), there would have been the kind of rotation certainty they ended up chasing unsuccessfully for the next few years. The five aces plan consisting of Rick Porcello, Justin Masterson, Clay Buchholz, Joe Kelly and Wade Miley resulted in a painful 2015, paving the way for the Red Sox needing to pay David Price $217 million for the certainty Lester would have provided for a lot less.

And when Price fell short of what Lester represented, the Red Sox needed to double-down one more time via the trade for Chris Sale, costing two of the best prospects in baseball.

The Red Sox obviously recovered. They have 2018 World Series title for proof. But Henry's mea culpa should come with a purpose, all the same.

They better have learned their lessons.

1. Pony up for certainty and don't lean on projections for important spots on the roster.

Extending Sale is somewhat of a risk, but you know what he can do in a Red Sox uniform on the stage of Boston. This isn't a guy who one might believe could evolve into an ace. He is an ace and most likely be one for the majority of his next contract. Sure, Nathan Eovaldi could become something more, as could Eduardo Rodriguez. But don't pin your hopes on what might be. Finding these sort of pitchers remain one of the most challenging feats in baseball, even if you do have money. Don't think for a minute replacing this position is a turn-key equation. It wasn't with Lester, and won't be for Sale. Now, this is a road the Red Sox are tip-toeing down with the closer spot. We'll see ...

2. Value the guy who can handle Boston.

This hasn't always been the case when it comes to the Red Sox prioritizing skill-sets, and it has cost them. It's nice to think a guy can play in this market, but until they prove it nothing matters. The Red Sox were convinced Edgar Renteria, Julio Lugo, Carl Crawford, Erik Bedard and Pablo Sandoval could handle this world. Not even close. It's why getting a chance to witness the likes of Steve Pearce and Nathan Eovaldi in action was so important. We now know they can live this life. Lester was great at it. For Price, it took longer than the Sox certainly banked on. Sale and Rick Porcello? Not a question.

3. Read the market and then don't mess around.

It's understandable when the Red Sox offer J.D. Martinez what they did because you never want to spend money you don't have to in order to secure a player. But with Lester, someone was going to pay him a heck of a lot more than $70 million. Remember Homer Bailey? He got a six-year, $105 million deal at the beginning of the 2014 spring training. Homer Bailey was never Jon Lester. Yes, he was two years younger, but do you think anybody cares about that right now? If nothing else, that should have been the starting point for negotiations. As we now know, it wasn't. Set your realistic price early and go from there. That's what Dave Dombrowski ultimately did with Price and that should be the model for Sale and/or Porcello.

It was good to hear Henry admit the organization's mistake back in 2014. But that's just Phase 1. Now comes the true trip to the mirror.

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