Breaking Down Alex Bregman’s Decision To Sign With The Boston Red Sox For $120,000,000 Over 3 Years

MLB Trade Rumors – The Red Sox are reportedly in agreement with Alex Bregman on a three-year, $120MM deal. The Boras Corporation client receives massive $40MM salaries in each season, though an unreported amount of that money is deferred. Bregman can opt out after each of the first two seasons. 

Bregman reportedly had a standing six-year offer valued at $156MM from the Astros for most of the offseason. The Tigers reportedly put forth a six-year, $171.5MM proposal, while the Cubs offered a $120MM guarantee over a four-year term. As of last month, Bregman remained committed to a long-term deal. The Sox’s willingness to offer one of the biggest AAVs in league history changed the calculus.

Damn!

I really though the Cubs had a chance at Bregman, but there’s no way you can expect a $40,000,000 AAV for that kind of player. When he was cheating? Absolutely. But with a 122 OPS+ in the 5 years since, and with declining walk and power numbers, there’s no reason to spend that much money. He’s simply not worth the numbers Boston gave him. That makes it much easier to move on as Cubs’ fans.

It still bothers me we don’t defer money as that seems to be the #1 reason he signed with Boston. That’s becoming a huge trend and the Cubs seem to be missing out/unable to commit long-term money under deferrals.

For the uninformed – the Red Sox promise $120M to Bregman, but they might only pay him $60M over the 3 years of the contract, and then $60M over a long-term period after the contract. It could be 10 or 15 or 20 years. The important thing is that it reduces the financial obligation RIGHT NOW which means less cash out of your pocket RIGHT NOW. The problem of course is that you need to pay the balance off in the future.

If Bregman helps the Red Sox to another World Series appearance, then it’s well worth the deferral and excessive obligation. If he sucks or it’s a bust contract, then you have a Bobby Bonilla situation for a couple decades.

It really bothers me that the Cubs do not have any notable deferrals at the same time every major team is deferring money. It’s like we refuse to change with the times because that would challenge Crane Kenney and Tom Ricketts to think differently. That really, really pisses me off… Much more than simply not getting Bregman.

The reality is the Cubs have a great young 3rd base option in Matt Shaw and are still linked to Justin Turner. It’s not an ideal mix compared to Bregman but it should be good enough come August, which matters most.

Overall, just really surprised someone paid for the 2018-2019 version of Bregman (.950 OPS, MVP runner up) when that player was very obviously cheating. I thought his AAV would be $25,000,000 over 6 years or closer to $30M at 4 years. Turns out that’s exactly what the Cubs had planned, but deferral money was able to push it over the top towards the Red Sox.

Hopefully this is not the single reason the Cubs fail in 2025. It’s starting to get really annoying that we hit on less than 10% of the free agents we pursue. Especially with how expensive it is to go to a game and how long it’s been since the Cubs were respected in the National League.

So while I don’t want to overreact to Bregman picking the Sox, and I don’t want to bitch before the season even starts, I just want to go on record and say it would be nice to see the Cubs as a legitimate Free Agency destination in the future because right now we’re a 2nd rate organization. Whether it’s because of budgets or deferrals or creativity.

Fact remains that we now have a very hard time signing big name free agents and it’s really starting to piss me off.

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