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Bradford: What if Mookie Betts didn't sign that deal?

"I don't love that we're going to be facing him or the next 10-plus years but I'm really happy for him. I'm so proud of him." - Arizona manager Torey Lovullo on the Bradfo Sho podcast.

You aren't going to find virtually anyone who isn't happy for Mookie Betts.


He works hard. He helps others. He listens. He cares.

If anyone was going to sign a 12-year, $365 million deal as a Major League Baseball player, Betts would be the guy to do it. In this weird world, that seemed about right.

But was it the right thing for Mookie to do? What if Betts doesn't sign that deal with the Dodgers?

Remember, up until that extension was announced in late July we were all zeroed in on what life was going to look like for Mookie when this time of year rolled around. For Businessman Betts, free agency was going to be the punctuation for a very business-like path.

Sure, there are some big-money free agents available as we sit here. Trevor Bauer. George Springer. Marcell Ozuna. But nothing like Betts would have represented.

The first question to ask is how much Mookie would have warranted in this market. Did he cost himself jumping at the Dodgers' offer? If we are to believe his approach was led by the bottom line than it is assumed Betts believed this is what the economics of baseball were going to allow for his life-altering deal.

When I asked two experts -- MLB Trade Rumors' Tim Dierkes and Steve Adams -- neither believed at first blush that Betts would be getting more than the $365 million.

They weren't alone. Many believe the COVID-19-induced economics of baseball simply wouldn't allow even the best of the best to approach Mike Trout's world of $400 million.

My best guess? I actually think he would have gotten slightly more. The three months Betts turned in, with the exclamation point that was a World Series championship, would have been powerful push for teams like the Mets, the Dodgers, and, yes, the Red Sox.

About those Red Sox ...

If you do believe that John Henry and Co. learned their Jon Lester lesson and extended themselves to what they believed was the appropriate level then so be it. But if that was the case we know it was a misguided calculation. Betts is worth more than 10 years, $310 million.

The question is how the Red Sox viewed Betts' existence after the 2020 season. Did they think there would be another shot at their guy, with another three months to define his true value? If they believed that it would have been another misread.

The Red Sox traded Betts to the one team that it was a better bet he would stay with than pushing aside when free agency came around. The Dodgers were perfect for Mookie in so many ways, and they only got more appealing with each passing day.

But for argument's sake let's say Betts gives the Red Sox another crack at it.

It's hard to believe that Chaim Bloom doesn't take a more aggressive run at Mookie, and with Alex Cora back in the fold it's plausible that the Red Sox come at the situation with a bit better perspective. Without the luxury tax limitations, this would have been all about defining the importance keeping a likely future Hall-of-Famer in one uniform for the entirety of his career. (When you have the option, you usually take it.)

The point is, my best guess is that the one certainty in this uncertain offseason would be the Red Sox prioritizing bringing back Betts. That means more money for Mookie. And factor in that you have at least two franchises with pockets just as deep -- the Dodgers and the Mets -- and the number keeps going up.

Betts undeniably has zero regrets. Same with the Dodgers. The Red Sox? Even with the promise of Alex Verdugo and all that Mookie Money that might be another story. They missed on their first chance, and never got a second.

It sure would have been interesting to see Mookie Betts, free agent. Oh, well.