Bo Knows

BY KEVIN KERNAN

If only the small market Red Sox and Yankees could keep up with those bold Orioles and super rich Blue Jays.

Sounds crazy, but that is what is happening this off season in the AL East where the heavyweights have taken a financial back seat to teams like the Orioles who brought in former Mets Masher Pete Alonso.

The AL Champion Blue Jays, who were just one horrific slider away from being World Series champions, are also loading up like there is no tomorrow – and could add free agent outfielder Kyle Tucker, too.

There will be no tomorrow in MLB after the 2026 season because a lockout is coming —and my guess is baseball will never be the same after that with the changes coming via Dr. Frankenmanfred, who can’t wait to destroy another baseball tradition.

But that is a column for Baseball or Bust come the middle of the week. Today, The Story is looking at the moving and shaking over the the weekend with the Cubs signing third baseman Alex Bregman to a five-year, $175 million contract, stealing him away from the Red Sox.

The Cubs have finally decided to spend some money.

Seems to me that both the Red Sox and the Yankees are taking this offseason thing a little too literal, don’t you think?

On New Year’s Eve I was on Rickie Ricardo’s terrific WFAN show and said loudly the Yankees need to forget about Cody Bellinger and focus on signing Bo Bichette, who smashes fastballs. I also noted the Red Sox need to forget about Bregman – who will be 32 in March and hit only .250 with a .724 OPS in the final 63 games of the 2025 season, and focus on signing Bichette, setting up a good old-fashioned battle between two rivals who used to hate one another.

At the GM meetings, Boras – who I have known since 1988, said – “I’m sure the Boston fans don’t want this to be just a cup of coffee.’’ It became just that. See you, latte, Alex.

Now more than ever, either the Yankees or the Red Sox must come away with Bichette. Messing up the AL East pursuit of Bo, though, is another team I mentioned as well, a team that must change its clubhouse mindset: the 96-win Phillies, who seem to fail in the postseason in some of the dumbest of ways.

On Monday the Phillies have a video call set up with Bo Bichette. That could really rock the Yankees and the Red Sox world if Bichette goes to the City of Brotherly Love. It also could just be a ploy to increase his price.

Working in the Phillies’ favor is this: the great Don Mattingly is now the Phillies bench coach, coming over from the Blue Jays, and Mattingly and ex-Blue Jay Bo are super close in their relationship and in how they view the way baseball should be played and the art of hitting. And there is no better hitting ballpark than Citizens Bank Park.

Why do you think Bryce Harper went to Philly? He thought the home runs would come easier there. Philly fans are tired of the Eagles after Sunday’s no-show in the wild card round of the playoffs and the loss to the 49ers.

Only Bo Knows where he will wind up.

Meanwhile, Bregman’s agent Scott Boras went the corny poem route and came up with a doozy for the Bregman journey, using a Starbucks coffee theme.

At the GM meetings, Boras – who I have known since 1988 – said, “I’m sure the Boston fans don’t want this to be just a cup of coffee.’’

It became just that. See you, latte, Alex.

Turns out it was the most expensive baseball cup of coffee ever, $40 million for one year of Bregman’s services and now he is a Cub — and the Red Sox are stunned.

Bregman signed that five-year, $175 million contract with the Cubs, who pursued Bregman last offseason. Plug in the $40 million that Bregman got from the Red Sox for one year of average play and you have a six-year, $215 million Bo-nanza, like the old TV show, thanks to Boras.

Bo Bichette is a Hoss of a player and he’s only 27, more like Little Joe of the MLB Ponderosa, represented by VaynerSports.

The Red Sox have painted themselves into a corner as have the Yankees. In one year, the Red Sox under former middle reliever Craig Breslow – and we all know middle relievers know best, at least that’s what they always tell you in the clubhouse – have managed to alienate many of the Red Sox faithful.

First, baseball chief Breslow signed Bregman to that three-year $120 million deal with two opt outs, without informing his pivotal player – his third basemen Rafael Devers, creating a Grand Canyon divide between Devers and the Red Sox.

Yet, how come when they get the top job, they always brag about their communication skills?

Devers was soon shown the door in a money dump trade to the Giants; get out of Beantown Raffy, and take your 215 Red Sox home runs and 747 Red Sox RBIs with you — and don’t let the door hit you in the ass.

The Red Sox squeezed into the 12-team postseason but were dispatched by the Yankees. The Red Sox were terrible in the wild card series, losing in three games. The Red Sox did not score in the final 12 innings of the series and yes, they greatly missed Devers – a Yankee killer – especially with young star Roman Anthony out with that strained left oblique, the swing as hard as you can on every swing injury of this modern era.

The Red Sox lost the series in the name of Payroll Flexibility. That payroll flexibility did not help them sign Bregman back. Oops.

The new-age POBO, president of baseball operations, that would be the middle reliever Breslow, knows much more than the media and certainly BoSox fans. The Red Sox a year ago signed Bregman to play on the same team as Devers and now both are ex-Red Sox. To be fair, Breslow did have eight saves over his 12-year career in 576 games, so he was on the field at the end of a victory on the rarest of occasions.

Overall, though, this is some really bad baseball planning.

Let me phrase it another way, this is some really arrogant baseball planning, thinking you are the smartest guy in the room. There is a lot of that going around in baseball right now and it provides BallNine with an endless stream of content.

The more important point is that both the Yankees and Red Sox, who usually mirror one another in good times and bad, have hit the rubber meets the road part of their off-season. Will the Red Sox go out on the free-agent market and bring back an offensive stud like Bo Bichette? Same goes for the Yankees.

Will they both lose out?

It is interesting to note that the frugal Big Market Cubs shut up their critics with the signing of Bregman and the trade for right-hander Edward Cabrera. That, along with the Bears’ miraculous comeback victory over the poorly coached Packers of Matt LaFleur – the Cubs had to do something to change their mediocre NL Central story. That is what I mean about where the rubber meets the road.

All these POBOs can spin their tales of coming future success for only so long and how they are on the right track even though the scoreboard and the standings say differently. You can only take the fans’ money in various ways in big markets before there is a rebellion of sorts.

The Yankees are standing on the precipice right now and it would even be more alarming for the Yankees, who are going on 17 years of not winning a World Series if the buffoon-like Mets could ever get their casino in order.

The Mets have a lot to do the remaining offseason. Maybe they will sign Kyle Tucker to change the narrative.

But I’m here to say good for the Cubs although that was an overpay of Bregman. But it’s only money. Sell a bunch more beer trains in the bleachers of the Friendly Confines and Bregman Beer will nearly pay for the player. Bregman does offer something else that is hard to find these days, true leadership. And that is what makes the Yankees failures so much more painful for their fans. They have the leader every team wishes they could have in Aaron Judge, yet they are wasting Judge’s prime years.

Bregman will give the Cubs what they need in that department. His teams have made the postseason the past nine years, by hook or by crook (2017 World Champion Astros) but I have always found Bregman to be an interesting guy when he is standing up in front of his locker after games talking baseball.

Same for Bo Bichette. The offseason theater has yet to play itself out, there is still time. For example, remember this, it wasn’t until Valentine’s Day in 2004 when the Yankees landed Alex Rodriguez in a trade with the Rangers.

Both the Yankees and Red Sox need to join the Blue Jays’ offseason party. This can’t be another year of “Hey, we like our guys.’’

The Blue Jays are trying to imitate the Dodgers, it seems, where they refuse to stand pat no matter how much success they had the previous season. For the Yankees and Red Sox that used to be their calling cards whenever I would bounce between their respective spring training camps in the Glory Days of the rivalry.

The Alex Bregman signing by the Cubs is a wakeup call for both Brian Cashman and Craig Breslow. The plans they put into place must be upgraded and that means spending big money and not being afraid of making the big trade.

Get to work.

Bo Bichette is waiting and only Bo Knows where he will wind up in 2026 and beyond.