Inside the Red Sox offseason failure and the Bregman contract holdups that caused it

In the middle of NFL Wild Card weekend, Alex Bregman finally lit the hot stove. By signing with the Chicago Cubs, Bregman sent one historic fanbase into euphoria and another questioning everything just one day after its fanfest. The timing couldn't have been worse.

Bregman signed a five-year, $175 million deal. Boras clients almost always take the best contract – and they're not alone in that regard – and the Cubs offer to Bregman came with far less question marks. In that sense, the Red Sox have no one left to blame but their front office for failing to meet the most basic of demands.

What the Red Sox got wrong in Alex Bregman contract talks

Deferred money in Bregman's deal

The Red Sox tried to take a page out of the Dodgers book, offering Bregman nearly as much overall money as the Chicago Cubs, but deferring the lump sum of his payments until after the completion of the deal. For some players, that's ideal. It gives them less money to spend during their playing days, sure, but it also ensures they don't blow it all in a few years time. Deferred money also provides a stable income for players after they've retired, as not every MLB All-Star can transition easily into media or coaching.

But that was not Bregman's prerogative. As Sean McAdam of MassLive detailed, Bregman has two young kids at home. He wanted to find a long-term home and support them right away. Bregman is set to play for his third team in three years. He doesn't prefer it this way, being away from his family for long spurts and moving them around the country. While the Cubs deal Bregman's signed also has deferred money in it, per McAdam, the Red Sox deferred dollars "stretching out decades".

No-trade clause

While Boston's deal came in at $2 million AAV less than the Cubs, the real sticking point for Bregman was the lack of a no-trade clause. Per McAdam, it is Red Sox organizational policy not to sign players to deals that include a no-trade clause. This doesn't make a whole lot of sense, but Boston already has an aversion to signing players over the age of 30 to long-term contracts. Bregman is 32, and wanted add-ons to his deal. Thus, it's not difficult to see why these two sides couldn't come to an agreement.

But again, Bregman has a family, and he is far from the only star MLB free agent who does. How do the Red Sox expect to compete for other family-oriented free agents if they're unwilling to include what is nowadays considered a fairly basic contractual provision?

Where do the Red Sox go from here?

Boston's failure to re-sign Bregman does not have to ruin their entire offseason. The additions the Red Sox have made, including trading for former Cardinals Sonny Gray and Willson Contreras, are encouraging. The likes of Bo Bichette, Kyle Tucker and a litany of starting pitchers remain available in free agency. This can be fixed.

Bichette, for now, seems like the most logical pivot for Breslow. There's a good chance Bichette will cost even more money than Bregman's $175 million since he is a few years younger. Bichette could also want that vaunted no-trade clause which Boston refused to give Bregman.

Now might be a good time for their front office to drop the act and finally join us in the 21st century. No-trade clauses go against the grain for any organization, but they're important to players, and can often be partial. For example, a NTC for Bichette could include, say, 8-10 teams he can outright refuse a deal to. That still leaves two-thirds of the league to work with.

Most importantly, the Red Sox must stop cycling through stars, especially if they want their homegrown talent headlined by Roman Anthony to feel comfortable. Boston's window is opening sooner than it expected. Taking advantage of that starts with making the right offseason moves, and dare I say breaking organizational norms when they don't fit the team's best interest.

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