CUBS MAY BE IN ON WILLIAMS & I'M GOOD WITH THAT

I’ll be honest: Devin Williams to the Yankees always felt like inviting a raccoon into your kitchen because “maybe it’ll cook.” Unnecessary chaos. A vibes sinkhole. A self-inflicted wound we absolutely did not need going into 2025.

The Yankees would have been perfectly fine rolling with the bullpen they had and making adjustments on the fly—shocking concept, I know. Instead, Brian Cashman decided to get cute and shipped off Caleb Durbin, a major-league-ready infielder who could’ve actually helped the Yankees in the spot they desperately needed help. And what did we get? A season of infield musical chairs, a bullpen that felt like a panic attack in real time, and Devin Williams… existing.

Honestly, I didn’t want him here. Still don’t.

But—maybe—the winds are shifting. The Athletic says the Cubs are rethinking how they build bullpens this winter, which is a polite way of saying: “We realized one-year deals for relievers is the baseball equivalent of duct-taping a broken chair.” They might even commit to multi-year deals for the right late-inning arms. No, not Edwin Díaz money, but real investment.

Naturally, Devin Williams—Counsell’s old Brewers closer—is on their radar, and apparently drawing enough interest that his next contract might stretch beyond what the Cubs are even comfortable with. They’re also sniffing around Pete Fairbanks. In other words: Chicago might actually give Counsell options instead of prayer candles.

So… what does that mean for the Yankees?

Simple: if Devin Williams packs up his changeup and leaves the Bronx, I will personally throw a parade. Streamers, confetti, the whole thing.

And let’s not pretend this saga hasn’t been a mess. Williams went through a full-blown confidence crisis this season and admitted it out loud after coughing up a loss to the Astros: “I stink right now.” He said he hasn’t felt like himself, hasn’t found his groove since Tommy John, and is basically fighting ghosts out there. This is not the energy you want anchoring your bullpen.

He’s a free agent after 2025, and of course Brian Cashman—king of familiarity hires and emperor of the “easy way out”—might try to bring him back. Why? Because it’s simple. Comfortable. Familiar. It’s classic Cashman: miss the big picture entirely, then pretend he’s playing 4-D chess while the rest of us are watching him knock over his own pieces.

Letting Williams walk would be the smartest thing the Yankees could do. His shaky performances made the bullpen wobbly, his beard policy drama created noise for no reason, and the whole thing even threw Luke Weaver out of sync. Domino effect chaos.

And sure, the Mets, Cubs, Dodgers, and Giants are reportedly interested in Williams. He’ll get his market. Some team will gamble on a bounce-back. Good for them.

Me? I’m praying the Yankees sleep through the entire bidding process. If Craig Counsell truly feels comfy cozy with Williams, then by all means—Chicago, come get your guy.

One less bullpen headache in the Bronx? Yes, please.

WHY IS BOONE ONE OF THE HIGHER PAID MANAGERS IN BASEBALL?

Aaron Boone's contract extension with the New York Yankees is yet another example of failing up in modern sports. Despite never delivering a championship as the Yankees' manager, Boone has become one of the highest-paid managers in Major League Baseball. Wait what? 

It’s a glaring reminder that in today’s world, success isn’t always about merit—it’s about connections and legacy.

Boone’s new deal, reported by Jon Heyman of the New York Post, is essentially a three-year contract through 2027. His salary jumps to $4.5 million this year, with $5 million and $5.5 million in the following seasons, totaling $15 million over three years. To put this in perspective, Craig Counsell and Torey Lovullo entered last season with the highest managerial salaries at $8 million and $5 million, respectively. The Yankees are paying Boone like an elite manager, but his resume doesn’t support it. As Newsweek pointed out, "it's worth noting that Craig Counsell (Chicago Cubs) and Torey Lovullo (Arizona Diamondbacks) reportedly entered last season with the two highest manager salaries at $8 million and $5 million, respectively."

Since taking over in 2018, Boone has posted a 603-429 regular-season record—a decent stat that some might use to argue his competence. But in the Bronx, regular-season wins are nothing more than a prelude. As Yankees legend Derek Jeter once said, “It doesn't matter what you do during a 162-game schedule. It all boils down to the World Series. Win a championship or it's a failure.” Under Boone’s leadership, the Yankees’ postseason record is a disappointing 22-23, with zero championships to show for it.

How does someone with Boone’s track record become one of the top earners among MLB managers? The answer seems to be more about who you know than what you’ve achieved. Boone’s name carries weight—his father, Bob Boone, was a respected player and manager. It's a guess by me, but it's a good one. It feels like the Yankees are more invested in maintaining a comfortable, familiar status quo than making the tough choices needed to win. Boone’s tenure represents a failure to uphold the Yankee standard of championship-or-bust.

Meanwhile, the Yankees claim they “have no money” to spend on infield help, according to Jon Heyman. "Yeah, I don't see it," Heyman said. "The Yankees, I don't think they're adding anybody. I'm told they have no money." The priorities are baffling: they can’t find room in the budget to strengthen the roster, but they can find millions to keep Boone in the dugout. He isn’t a strategist or a motivator—he’s a babysitter for a team that often looks rudderless in October.

The real frustration should be aimed at the top. Hal Steinbrenner and Brian Cashman have shown they’re more than willing to spend—just not in the right places. Boone’s bloated contract is a slap in the face to fans who expect excellence, not mediocrity. If they really wanted to win, they’d put the money toward impact players or, better yet, an actual qualified manager who knows how to get the most out of a roster.

The truth is, as long as Yankee Stadium is filled with fans and the merchandise flies off the shelves, the organization won’t change. The Steinbrenner family doesn’t view a season without a championship as a failure anymore—they view it as business as usual. Until the front office recognizes that mediocrity is unacceptable, the Yankees will remain in this frustrating cycle of good-but-not-great seasons.

For fans, the message is clear: Stop rewarding mediocrity. As long as tickets are sold and ratings stay high, nothing will change. The only way to reclaim the Yankee legacy of excellence is to demand it. That starts with holding Aaron Boone—and the entire front office—accountable for their failure to bring a championship back to the Bronx. That's my opinion of course.

CASHMAN: WE ARE GOING TO BE A PHOENIX RISING OUT OF THE ASHES IN '24.

I have never laughed so hard in my life. Well, maybe once. But it was for a good reason and certainly not at the silly little one-liners Brian Cashman is dishing out in Arizona this week to the media. Now, Casey gave a great overview on what has been said by both Cashman and baby boy Hal Steinbrenner in his piece THE NEW YORK SPANKEES. I want to focus on one of the final soundbites that Cashman spooled out this week, “This winter, we go back at the wheel and it’s now about ’24,” Cashman added. “We look to be a phoenix rising out of the ashes to find a way," reported The New York Post. Yeah. Let's pause that for a moment and unpack.

Does Brian Cashman actually think that the Yankees are going to rise out of the ashes to find a way to a pennant? That's like me saying, I am going to a sub four-hour marathon without making any changes to my running discipline, training and work sessions. If the Yankees want to bring change, then they actually need to back that up, not skate the questions of how with nonsense like rising from the ashes. This is not Harry Potter for God's sake. 

“I know people want change just for change’s sake,” Cashman said. “I remember seeing great people walk in and out of this place like Pat Gillick before I got here, a Dick Howser or Lou Piniella, all these guys, because of impatience or we’re not tolerating the ebbs and flow of what the game brings sometimes," reported The Post. I'm sorry, has the last 14 years been just ebbs and flow? These are years we simply won't get back. And the fact that they don't realize this and are staying the course is just making us look foolish.

Cashman has no answers except to say that we need to win more ball games. How Brian? How do you propose the Yankees do that? What is the plan? What is timeline? What are the milestones and expectations? Throwing out silly cinematic lines, similar to the puppet they have in the dugout game after game, just isn't going to be tolerated anymore. I think the Kool Aid tank is empty. No one is buying this. I can't imagine the players are. 

What I hope is that the players take more matters into their own hands. Almost managing themselves and pushing back. Back in the day, we had player managers in baseball. Maybe it is time for that again. Because right now, the narrative isn't being written by the players. It is being written by public relations puppeteers and the last straw is the phoenix analogy.

If I was a free agent, I wouldn't want to come to the Yankees to play. They no longer hold the status they once did. I would rather go play for a manager and organization that backs up their claims to win. Like the Chicago Cubs and their new manager Craig Counsell, or Ron Washington at the Anaheim Angels. Of course, there are the clubs that actually made it to the ALCS and NLCS, and their leadership (minus Houston of course). They are the teams to watch. Backed by leadership, unafraid of change, willing to accept and use their mistakes as opportunities. 

So, until Cashman and his clowns consider some wise words by a franchise herself, Taylor Swift "It's me, hi, I'm the problem, it's me. At tea time, everybody agrees. I'll stare directly at the sun but never in the mirror. It must be exhausting always rooting for the anti-hero," they will go nowhere but right where they are now. Yea, I can be cute and creative too, Cashman. Stop treating us like fools. 

-- Suzie Pinstripe
BYB Senior Managing Editor
Twitter: @suzieprof