Contract negotiations aren’t for the faint of heart in pro sports.

The latest example comes from Boston, where WEEI Radio host (and former Red Sox player) Lou Merloni details just how far away the Red Sox have been from re-signing Mookie Betts to a long-term deal.

.@LouMerloni says the #Redsox offered Mookie Betts a 10 years, $300M deal in the 2019 offseason. Mookie countered with 12 years, $420M



Lou says Mookie and the Sox have been off by $100M or more in the past 3 negotiations not including this past offseason pic.twitter.com/zfMt2n1Ske — OMF (@OMFonWEEI) January 28, 2020

“I’ll tell you what I was told. They have made multiple attempts to sign Mookie Betts throughout his career,” Merloni said on the OMF (Ordway, Merloni, Fauria) Show on WEEI on Tuesday. “There’s a couple reports out there publicly that they offered him five and 100 (million) a while ago. Eight and 200 (million) was the one that everybody talks about. 2019 offseason, there was another offer that was rebuffed. And that offer was—you’ve seen some of the contracts that have been out there so the tables were set—in the 10/300 (million) range, and it was countered with 12/420 (million).

“Now, I would say this: In the three offers they’ve made, they’ve been off close to $100M. Off by close to $100M in offers! And that 2019 offer was off by more than $100M. So three years in a row, they’ve made efforts to try to sign this guy. They signed Xander Bogaerts to an extension. They signed Chris Sale to an extension. Does anybody not think there hasn’t been talks this offseason?

“Now, I don’t know as far as how talks went with another bid at this,” Merloni continued. “But the fact that they are actively shopping him shows they can’t get it done. They know they can’t get it done. When you go to a guy three years in a row and you’re off by $100M, you know you can’t sign him. And I don’t think this organization is willing to give $400M. That’s what I was told. I don’t think it’s going to happen.”

This, along with Red Sox ownership being allergic to the luxury tax, likely is spurring Betts trade rumors on a daily basis. Boston knows Betts is headed for free agency in year, and likely doesn’t feel comfortable playing in a market that could include the Dodgers, Giants and Mets.

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Betts, 27, posted a .915 OPS and slugged 29 home runs last season. In six big league seasons, Betts has racked up 42.0 WAR, putting him on an early track for Cooperstown. That track will likely soon continue outside of Fenway Park.

Joe Giglio may be reached at jgiglio@njadvancemedia.com. Follow him on Twitter @JoeGiglioSports. Find NJ.com on Facebook.