Can Red Sox learn from Jon Lester saga when dealing with Mookie Betts?

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Remember this quote from John Henry last February?

"I think we blew the Jon Lester -- we blew that signing in spring training," the Red Sox principal owner 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."

It took five years, but Henry finally publicly acknowledged where it went wrong with the Lester situation, a misstep that had the Red Sox chasing their tail for the next few years. 

Where the Sox messed up is easily identified. They tried low-balling Lester, offering him four years, $70 million when a more realistic proposal would have easily gotten the job done. (Lester said a year later in a WEEI interview that if the Sox offered something in the vicinity of five years, $120 million he would have signed.)

What happened after that initial offer was a mess. 

Lester's representatives never came back with a formal counter-offer, knowing that it would have to be outrageously high in order to find some sort of common ground. Part of their fear was that the exorbitant figure being leaked out, making it appear as though the pitcher wasn't realistic about the situation. Sound familiar?

As WEEI's Lou Merloni reported this week, the Red Sox have tried to get an extension done with Betts, all the way up to offering him a 10-year, (I've heard) $310 million last spring training. This time Betts and his reps came back with a counter: 12 years, $420 million. 

The overwhelming reaction immediately turned into a "thanks but no thanks" from the Boston baseball fans to a player most desperately want to keep. The perception was that it was simply much to one player, as good as that player is.

So, what can the Red Sox learn from the Lester scenario? First of all, whatever the Sox are legitimately willing to pay Betts better be along the lines of what that final offer will end up being. If they are never going to go over $400 million, for instance, then make that clear and gauge the reaction from the player.

But this isn't apples to apples when comparing Betts to the former Red Sox pitcher.

While the number Lester never gave for fear of misrepresenting what he was truly looking for, the $400-plus-million figure countered by Betts probably isn't far off from what he is legitimately looking for. The notion is that the Sox' star is banking on having a monster year in 2020, putting him back in the Mike Trout conversation. Yes, the same Mike Trout who signed a 12-year, $426.5 million extension last spring training.

Whatever avenue the Red Sox end up going down with this Betts situation there is something that lines up perfectly with what happened regarding Lester: For the sake of their future, Red Sox can't blow it.