Red Sox: Did Mookie Betts make a mistake by not re-signing with Boston?

This past winter the Boston Red Sox traded away Mookie Betts amid a contract standstill, but did the superstar make a mistake by not re-signing?

Things haven’t been going the best for the Boston Red Sox since winning the World Series in 2018. Between injuries, trades, payroll slashing, a cheating investigation, and now the coronavirus halting the season, it’s not much fun being a Red Sox fan. Of those things though, it feels like one could’ve truly been avoided, trading Mookie Betts.

Now that we’re several months removed from the trade that shook the baseball world, the dust has settled and things seem a little clearer, kind of. It was obvious this winter that Boston was hellbent on slashing payroll to reset their CBT penalty marker for the 2020 season, this meant wheeling and dealing. The biggest line on the ledger belonged to lefty veteran David Price, who still had 3-years/$96M left on this contract. That’s one hell of a chess piece to try and move unless you have the right bait.

This is where Mookie comes back into the equation. All offseason we speculated just what it would take to move Price as it was clear that he had the target on his back. I don’t think anyone thought that Boston’s best homegrown talent in a generation was the ticket to the deal, but it was the spark.

Former Red Sox infielder Lou Merloni was a recent guest on Barstool Sports’ “Section 10 Podcast,” where he and the hosts discussed a myriad of topics, including Betts. Merloni brought up that before the coronavirus shut the league down, he was expecting Mookie to fetch anywhere from $380-$400M next winter, but now he wasn’t too sure.

Since everything hit the fan, I’ve been thinking about the future, but haven’t once thought about that trade, but Lou got me thinking.

What if Mookie had signed one of the deals that the Red Sox had offered him? On the surface, it feels like we’d be looking at a completely different landscape. Obviously he wouldn’t have been traded, but who exactly would Boston have had to throw in to move Price? There’s a good chance that Chaim Bloom would’ve needed to toss in some prospects, the same sin as his predecessor.

The thing is, some of the deals that Boston offered Mookie were laughable, but the last one was at least in the region of what Betts had in mind. We all heard about the numbers during the offseason, the Red Sox were hovering around 10 years/$300M but Betts was eyeing 12 years/$420M. It’s clear where Mookie wants to be in regards to salary and rightfully so as he’s earned every penny.

Like Lou said though, those numbers were before the economic crisis we’re flirting with and the baseball world doesn’t have that kind of money to throw around right now. When this season was initially delayed the MLB and MLBPA came to terms on a deal that would allow players to count this season whether it’s played or not. So no matter the outcome of 2020, Mookie is a free agent next winter with a very uncertain market.

What’s his next move? If we do get a season, it’ll be without fans which will seriously hinder any of the big organizations in the spending department, and crippling Mookie’s earning potential. It’s hard to imagine him getting anything close to that $420M with the owners losing out on all of that fan-generated revenue. This brings us back to my original premise, did Mookie make a mistake by not accepting one of Boston’s offers?

I can’t even imagine what’s going through Mookie’s mind right now as the season continues to be delayed. I’m sure at least once or twice he’s second-guessed his decision to not sign that last contract, but then again he’s a man that knows his value and worth to any team he’s on. It’s hard to not think that he made a mistake by not re-signing with Boston, but then again, none of us saw the pandemic coming.

It’s pretty clear where the Red Sox wanted to be in the negotiations and where Mookie wanted to be, Betts wants that Mike Trout money. When I hear the phrase “Trout Money,” it reminds me of the wrestling wars of the 90s between WCW and WWF, where the phrase “Sting Money,” was used to negotiate contracts. Sting was the jewel of WCW and the highest-paid wrestler in the business at the time. It sounds a lot like a certain outfielder that plays in Anaheim.

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So, if Mookie accepts the last offer from the Red Sox he’s still in Boston and has guaranteed money for the next decade. However, by not accepting, he now has a chance to maximize his worth and cash out on a contract that could see him through his career. When you look at it from a few steps back he was damned if he didn’t and damned if he did. We won’t know the true outcome of the saga until next winter.

Mookie Betts is more than worth every penny that he wants to be paid, and I can’t even begin to tell him otherwise. He’s worked his entire life to get to this point and is doing just what someone in that realm should, looking out for himself, and by relation, the rest of the league. If Betts can negotiate a high-end deal then that opens the door for the rest of the league as the salary ceiling rises.

Only time will tell if his choice to turn down the Red Sox and test free agency will pay off. If things were normal and we were into the second month of the season, I’d say he made the right move. Hindsight is 20-20 though and as the 2020 season continues to be postponed, it’s hard to think about that $300M on the table and not regret leaving it. Mookie Betts is one hell of a player and I’d love to see him again in a Red Sox uniform, but for right now, I’d just love to see him play period.