Was Mookie Betts situation repeat of Jon Lester fiasco? John Henry says no.

Rob Bradford
February 17, 2020 - 3:01 pm

FORT MYERS, Fla. -- Did the Red Sox offer Mookie Betts enough money?

It is a pertinent question considering where the two sides landed, with the Sox needing to trade Betts to the Dodgers after recognizing there was a good chance he was headed to free agency after the 2020 season. And considering it was just about one year ago that Red Sox principal owner John Henry told the assembled media on the first day of spring training that his organization had messed up the Jon Lester negotiations leading into the 2014 season, it was worth asking if history had repeated itself.

"I think we made legitimate offers over three offseasons but I really don’t want to — I’ll follow Sam’s point about not getting into what happened," said Henry, referencing team president Sam Kennedy while addressing the media Monday morning at JetBlue Park. "But we made it clear to Mookie, I made it personally clear one-on-one, that we wanted to see him in a red sox uniform for the rest of his life if possible but as I went through in my opening statement, we live in a different world today. Players spend so many years being underpaid in the system that we have that when they get to free agency they’ve earned the right to maximize their chances of being paid maximum amount."

"I go to sleep at night thinking that maybe we could've made another offer to Jon Lester that maybe we would've bridged the gap," added Red Sox chairman Tom Werner. "I think we made (Mookie) what we consider fair and generous offers. As John said, I think it was all right for Mookie to want to test the market."

The ownership group made it clear throughout the press conference that efforts had been made to lock up Betts to an extension. League sources put the Red Sox offer last spring training at 10 years, $310 million with WEEI's Lou Merloni reporting the outfielder countered with a 12-year, $420 million deal.

Betts talked to WEEI.com in September about the first time the Red Sox approached him with an extension offer, the year before he was arbitration-eligible.

"That was a really emotional time because I was like, ‘Mom, we’ve never seen this amount of money.’ She was like, ‘OK, cool. It’s a lot of money. I think we know it’s a lot of money. So let’s focus on the facts. Let’s focus on what is real and we took the emotions out of it.' The first one was definitely the hardest," said Betts, who agreed to a one-year, $20 million deal last offseason. "At the time we had never seen anything like that."

Leading into the 2014 season, the Red Sox lowballed Lester with an offer of four years, $70 million. For fear of a high counter-offer being leaked the Lester camp instead waited for the Red Sox to come up with their offer to closer to market value. That never happened. Lester would later explain during an appearance on WEEI that he would have taken a deal in the vicinity of five years, $120 million.