lesterDid you see Jon Lester pitch for the Red Sox against the Yankees a few days ago? I bet you more money than Floyd Mayweather made in his fight against Manny Pacquiao that you didn’t.  There is no way you could have. That’s because Lester does not pitch for the Red Sox anymore. Why? Well, probably because of a poor initial offer.

Lester was drafted by the Red Sox at the age of 18. He played 8 seasons for the organization. He won two championships, pitched a no-hitter, and even beat cancer with the ballclub. Despite his impending free agency after the 2014 season, Lester was not shy about declaring his love for the city and his desire to remain playing for the Red Sox. That’s where he wanted to be.

To start negotiations, the Red Sox made Lester (who is still in the prime of his career) an initial offer to rejoin the team. The number they chose was a monumental mistake. It instantaneously erased years of goodwill. It immediately paralyzed the negotiations.

The number was $70 million. I know, I know . . . that’s a ton of money. But not for a player of his caliber (who also happens to be left handed). Not when your market value is much more. With their initial offer, the Red Sox wanted to say: “Let’s get the ball rolling.” What Lester heard was: “We don’t value you.” It was seen as a sign of disrespect.

Now, Lester plays for the Chicago Cubs. He got a 6-year contract worth up to $170 million. Ultimately, the Red Sox did offer Lester a contract upwards of $100 million. The damage, though, had already been done. It was irreversible.

Here’s what we can take from this. The next time you see Lester pitching a shutout, let it serve as a reminder to think twice about your initial offer – whether it is an offer of employment, an offer in collective bargaining, or an offer to settle in litigation. It could determine whether you end up being the “winning team.”