Friday Four-Pack 8.1.25

Red Sox fail the trade deadline. Mike Felger tabbed most influential in Boston. Dave Portnoy gets CAW'd. MutStack notes!

“Absolutely,” said Kennedy. “We have the ability to do that in terms of, you know, a blessing from ownership, and fulfilling our goal of becoming a postseason team. That said, we have to start playing better baseball on a more consistent basis…So to answer your question - yes, we do have the ability to go out and improve the team.”

That was Red Sox CEO/Used Car Salesman Sam Kennedy back on July 3.

Four weeks later, a mere five games back in the AL East and possessing a Wild Card spot, his Boston Red Sox did nothing at the MLB Trade Deadline.

Well, they did snag reliever Steven Matz from the Cardinals. And the Dodgers, who we’re begging someone to take Dustin May off their hands, they found a trade partner in the Red Sox and shipped him and his 4.85 ERA to Boston. That ERA, by the way, ranks 73rd of 82 pitchers who have a minimum of 100 innings in 2025. Awesome! So yeah, basically nothing.

Another pathetic showing by the organization.

Just a few weeks ago, CNBC reported that Fenway Sports Group was valued at $14.19 BILLION - the fourth-richest sports empire in the world. And yes, ownership deserves some blame for how this Trade Deadline played out.

They pushed to trade Rafael Devers and dump 100% of his salary. That meant the return was going to suck (shoutout Jordan Hicks). If they had eaten some of that contract, maybe more teams would be interested, and the return would have been better. But because the Sox are driven not by winning but by their bottom line, that didn’t happen.

One report said money was a factor as the Sox were assessing trade deadline moves. So sure, blame John Henry. Blame Tom Werner. And certainly blame Kennedy, who is as likable as a piece of gum on your shoe.

“Thanks, Bres, you f*&king stiff.” - that scout that got fired and every Red Sox fan. Probably.

Me? I’m putting this mostly on Craig Breslow. After getting nothing of note for Devers, he followed it up with what Ken Rosenthal called “An epic fail” on Deadline Day.

A few weeks ago, Breslow and Underdog’s Jared Carrabis had a long off-the-record talk on the field at Fenway. Jared’s public takeaway was simple - Breslow is a really smart guy, and would a really smart guy strongly insinuate that the team would be aggressive at the trade deadline and then really do nothing?

Turns out, yes. That’s because Breslow, like Kennedy, is happy to lie to the fanbase. They both think you, the fan, are stupid and have no problem looking you in the eye and just…lying to you.

Breslow continued with his bullshit on Thursday night. Chris Cotillo of MassLive reported the Red Sox and Twins were “Not even close” on a deal for starter Joe Ryan. Rosenthal followed that up later by describing Breslow’s attempt to land Ryan, “feeble at best.” Ha.

And yet, there was Breslow, telling the media via Zoom (in 2025?) that the team had aggressively pursued multiple big names, but the problem was that the team’s prospects weren’t good enough to get a deal done.

“We pursued a number of really impact possibilities ... Ultimately it takes two teams lining up for those teams to lineup ... Teams have to like our players in order for that to happen."

1. As the team’s GM, you probably shouldn’t admit that publicly.

2. Oh, so you’re minor league system sucks now, and it’s Chaim Bloom’s fault? Got it.

Just brutal. Let’s take a look at the teams competing with the Red Sox for a playoff spot after the trade deadline.

Yankees - better. Mariners - much better. Rangers - better. Astros - better. Rays - better. Royals - probably better. Jays - better.

They all added. You? You got a reliever who might end up starting for you, and a starter who the current World Series favorites were happy to trade. I’d love to see the Sox players’ group texts, as the team did nothing on Thursday. Management assured them the Devers trade was not giving up on the season. How do you say that and then do nothing at the deadline???

I hope Alex Cora speaks his mind later on Friday. He did a year ago when, again, the team stood pat. “Honestly, we didn't get better," he said. "We just stayed the same, and the teams around us got better.” This year’s team is better than the 2024 version, yet the team still could not be bothered to make real additions.

The fans? We’ll see how they respond this weekend with the Astros in town. Dodgers fans dominated Fenway last weekend, and it won’t be shocking to hear a large Houston contingent take over this weekend.

On the field, this has been a fun team to watch. And I guess they could still sneak into the playoffs. But that’s not the story. The story is that the Red Sox were once again in a position to add to an already good team. They told the fanbase publicly they’d improve. Privately, they whispered to Carrabis and others that, of course, they’d add. But when it came time to pull the trigger, they came up empty. Again.

The Interest Kings are not to be applauded for almost making a big move. Breslow and Kennedy have proven their words are hollow and their promises are empty.

Breslow went on WEEI Friday and said he doesn’t think there was much more he could’ve done to improve the pitching at the deadline. Kennedy will probably be a pregame guest on NESN Friday. And then Breslow will probably join Dave and Lou in the booth on Saturday. They’ll both tell the fans how hard they tried at the deadline and how invested they remain in this Red Sox team. They’ll emphasize their commitment to winning at the highest level. 🙄🙄🙄

They’ll both be lying to you. Again. The same way the entire organization has been for the last half-decade.

At this point, it’s your fault if you actually believe them.

Meanwhile, the Boston Globe calls Michael Felger the ‘most influential person in Boston.’ Dave Portnoy gets a lesson on betting on horses in 2025. And one lawmaker wants to BAN prop bets.

All ahead in this week’s Four-Pack.

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On the Boston Globe profile of Michael Felger…

We can start by answering the question posed in the headline of Joon Lee’s lengthy profile, “Is Mike Felger the most influential person in Boston?”

Certainly not.

And I have no clue who actually might be. Dave Portnoy does not live in Boston, but even from New York/Miami, the founder of Barstool Sports is an influential figure over the city from which he launched his empire. Patriots owner Bob Kraft is somewhere on the list. Wyc Grousbeck, too. Hell, Grousbeck was atop Boston Magazine’s recent ‘2025 Most Influential Bostonians.’ The piece ranked the Top 150 according to their influence, most of whom I had never heard of.

Felger did not make the list. And he shouldn’t have. A few weeks ago, he admitted there are specific topics he won’t even talk about on his own show.

“I’m afraid to fully…I’m afraid to say the wrong thing,” Felger told his co-hosts a few weeks back. This was in response to a caller commenting on a segment regarding Jaylen Brown, race, and politics from the day before on Felger and Mazz.

“You know, talking about sex, politics, and race, and you just, you say something wrong. And that’s it. So, I don’t want to lose my job, cause you people have turned into a bunch of a-holes. They try and fire people for saying something wrong. So, I’m bringing it up, I’m leading the horses to water, but you’re going to have to drink. I’m afraid to say anything. And it’s your (the listener’s) fault. It’s your fault.”

It’s hard to label someone as the most influential when they’re blaming their audience for avoiding discussions that might come across as polarizing.

And my guess is that Felger would actually like to blame his bosses and say that they wouldn't have his back if he said something stupid, but he can’t, I get it. But blaming the audience was weak. Not to mention that here in 2025, we appear to finally be free from the cancel culture that loomed over media for years. Felger’s smart, he knows that. I digress.

Am I nitpicking the headline? Sure, but that’s why I started this newsletter/part-time podcast two and a half years ago, so that I could react to profiles like this, especially since no one else is going.

Most influential person in Boston? No, sir. Most influential person in Boston sports media? Absolutely. But writing about Felger’s influence on sports media is not as sexy. Certainly, the influence over his audience is there; you can see it in the ratings and in the number of fans who parrot his takes day in and day out.

You can also see his influence on fellow sports radio hosts and content creators, some of whom have clearly adopted Felger’s style and approach. For most of them, it hasn’t worked. The same thing happened in New York when Chris ‘Mad Dog’ Russo’s style was adopted by other hosts in the market—and still is to this day. There will only be one Mad Dog, just like there’ll only be one Felger.

He’s a huge success, seems like one of the hardest-working guys in media, and deserves whatever praise comes his way. That being said…

Massarotti keeps things from flying off the rails. If Felger is the accelerant, Mazz is the afterburn — grimacing, interrupting, pushing back just enough. He gives the show shape and rhythm, keeping it from veering into total cynicism. He’s part instigator, part guide — someone who knows when to challenge Felger and when to let the chaos cook.

Um, what?

Mazz hardly ever pushes back on Felger. That’s one of the reasons I think the show has slipped in the ratings - the only tension is between the show and the audience. When Mazz does push back, he is often bullied by Felger into circling back to eventually agreeing with the show’s host. If anything, Jim Murray will occasionally offer a differing view. But Mazz, “challenging Felger?” I listen to the show a lot, and I don’t hear it.

As Boston changed, The Sports Hub’s biggest rival, WEEI, calcified around an old idea of Boston that was increasingly out of step with the city. In the early 2010s, the station’s identity started to drift. (I was an intern at WEEI in 2013.) Its banter began to curdle into something more overtly political. Some shows veered into broader social commentary, often echoing the language of Fox News. On-air debates drifted from pitch counts and power players to rants about race, gender, and grievance. Sports talk blurred into something else entirely.

Felger didn’t rise to the top of Boston media because WEEI was talking politics and he didn’t; Felger benefited from being consistent with his message, doing a different show every day, and being very good at his job.

And people roll their eyes when they hear this, but he and 98.5 The Sports Hub beating their competition to an FM signal while Entercom’s (now Audacy’s) CEO promised his employees that AM radio was still popular, that was a big deal.

“I wanted to do more of the stuff we weren’t doing on WEEI,” Felger said. “Classic sports talk radio has been critical, fast-paced, topical, and not drifting around and losing focus. Did I mention being critical? It’s important for sports radio. It’s a critical medium.”

WEEI wasn’t critical? Bill Simmons got his start shitting on Glenn Ordway and WEEI for always being critical. I was told that Felger left when Jason Wolfe and could not find a full-time role for him, or something like that. I’d love to read a deep dive on how that went down.

Felger didn’t bend the city to fit him. The city bent toward him — and toward the many Bostonians like him who’ve shaped what it’s becoming.

The piece is well-written, and its author, Joon Lee, is a much better writer than your humble newsletter publisher. And I give Lee credit for pointing out that, for all this perceived influence, Felger and Mazz are down 34% in the ratings from this time last year. But the whole Felger/Marty Walsh/Michelle Wu/New Boston/Old Boston angle…it didn’t work for me. For a lot of the reasons above.

There’s no debating Felger’s influence on sports fans and sports media in Boston. But how much he’s influencing Boston as a whole is up for debate.

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On Dave Portnoy feeling the pain of CAWs…

BUT…the CAW groups are hammering the excata pool. And trifecta pool. And superfecta pool. You’re seeing some seriously depressed exacta payouts, and people are noticing.

I grew up playing exactas and exacta key boxes, but I’m bailing on them at Saratoga for now. I’ll focus on win bets, daily doubles, and the Late Pick 5, where supposedly the CAWs are still barred from playing. On the win end, especially, I think you can still find some value. I’ll probably end up playing in more contests, too.

I wrote the above just a few weeks ago, in a newsletter where I also highlighted the monster Barstool/Fox Sports deal.

Based on Dave’s tweet, I guess we can confirm- he’s not a MutStack reader. Well, he’s probably a subscriber who was just so busy with the Fox deal that he missed that week’s edition. Understandable. I’ll let it slide.

Yep, I’m writing about Computer Assisted Wagering groups. Again. And I’ll keep doing it until the industry wakes up and takes action.

To their credit, NYRA (The New York Racing Association) has done something. In 2021, they shut off these big CAW groups from betting in the win pool with two minutes to post. This prevents CAWs from sending huge win bets late and drastically adjusting the final odds after the race starts, as I examined in this video.

That has forced the CAWs to attack the exacta pools, and unless you’re closely watching the will plays, you’re likely to be annoyed at how low a NYRA exacta pays in 2025. The upside is that there’s increased value betting to win, plus you don’t have those insane odds drops after the gates open - the kind that are embarrassing to the sport and make people feel like there’s insider trading going on.

The kind you got Sunday at Delmar, where Lovesick Blues was 45-1 just a few seconds before the gates opened. The first flash of the odds once the race started showed the horse at 18-1…and you’ll never guess who won!

This has happened so much at Del Mar this summer that they are finally adopting the NYRA policy of closing the win pool to the CAW bettors with 2 minutes to post. That started Thursday, and those late odds drops disappeared.

What NYRA and now Del Mar are doing should be the industry standard. Is it perfect? Nope. And with rebates, superior tech, and bankroll, plus the ability to bet right up until the last second in every other pool, they have MAJOR advantages.

But this one safeguard is a step in the right direction. It’s better for the sport and makes it better for the bettor. Now we just have to get he rest of the tracks in the US on board.

With Portony - the most popular horseplayer in America - complaining about it, maybe we can make it happen.

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On a push to ban prop bets in the Ohio…

First, MLB was investigating gambling allegations against Guardians pitcher Luis Ortiz. This week, his teammate and closer Emmanuel Clase was also added to MLB’s investigation into connections to sports betting. There’s no report on what they’re looking at with Clase, but one X.com user has some evidence that it could be similar to the Ortiz situation, where Clase was purposely not throwing a strike on his first pitch of certain appearances.

Yes, you can bet on whether a pitch will be a ball or a strike. The suggestion would be that sports bettors knew when Clase was going to miss with the innings opening pitch, and profited from that knowledge.

Rather than criticize the players for allegedly getting involved, Ohio Governor Mike DeWine wants Ohio to ban prop betting in his state.

“The evidence that prop betting is harming athletics in Ohio is reaching critical mass. First, there were threats on Ohio athletes, and now two high-profile Ohio professional athletes have been suspended by Major League Baseball as part of a ‘sports betting investigation.’ The harm to athletes and the integrity of the game is clear, and the benefits are not worth the harm. The prop betting experiment in this country has failed badly. I call on the Casino Control Commission to correct this problem and remove all prop bets from the Ohio marketplace.”

The problem, of course, is that the Casino Control Commission only has say over the regulated markets, for example, DraftKings and FanDuel. Unregulated sportsbooks are easily accessible for nearly everyone. If Ohio bans prop bets, bettors will still be able to bet them - this move would only grow the offshore and unregulated markets.

Regulated markets help catch players who are working with sports bettors. Without their oversight, there would be more athletes involved in scandals like this. NBA players Jontay Porter and Malik Beasely were caught because prop betting is legal, and there are regulatory groups that monitor betting on everything.

Rather than blaming sports betting and prop bets, how about blaming the athletes who decide to go against the rules and get involved?

You may not like sports betting, but its legal and regulated markets are one of the only ways to ensure that the players who tip off gamblers get caught.

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On your MutStack Notes…

🏀 A tough loss for Team KMS Monday night in Berlin, CT. Full credit to Barstool NY for the win - they killed us on the boards and played the better game, but it was a disappointing end to the KMS/NY Trilogy. Tied 18-18, I thought we’d go on to win, but the shots didn’t fall.

It didn’t help that one of the officials thought he was Jim Burr out there, but that’s not why we lost.

I’ll miss the practices with Team KMS the most. Forced to watch the game from the sidelines with my trusty crutches, I shuffle back to being a retired basketball player, just hoping to get back to full health sometime in 2025.

🎙️ This picture of Jones and Keefe at Fenway with WEEI management sparked some somewhat reckless, “Jones and Keefe back to afternoon drive???” thoughts from this washed-up radio host. But I’ll say this - it did the same for at least a few other current/former Boston sports radio hosts/personalities as well. 👀👀

🍿 Happy Gilmore 2…it was fine for what it was. The ending was brutal, but I liked the PGA cameos. Travis Kelce…good actor? Kids laughed a lot. It is not the worst movie ever.

🏈 From Andrew Callahan’s excellent Pats Camp coverage - “Speaking of the playbook, McDaniels has embraced Maye’s mobility by installing more bootleg play-action passes, movement throws, run-pass-options (RPOs) and designed quarterback runs than we’ve almost ever seen from his system. Were it not for the Cam Newton-powered Patriots offense of 2020, this would be near unprecedented for McDaniels. The Patriots’ offense will have new flavors in 2025.” Yes, please.

🏈 I would 100% trade a third-round pick for Terry McLaurin and give him $30 million a year. Do I think the Krafts would do that? Not a chance.

🚗 The plan was to have today’s newsletter posted by 8 AM Friday, but, hand up, I got caught up in watching way too much of the KMS Boys and their road trip this week. Producer Justin Trudell picking the Pats to go 15-2 was not the craziest thing I heard from the crew, but it’s close.

💰 DraftKings continues to dominate the sports betting market in Massachusetts. The most recent monthly numbers showed them with a 50% market share, a whopping 25% ahead of their closest competitor, FanDuel.

They’ll be digging into their own deep pockets to pay a massive $450K fine handed down by the Massachusetts Gaming Commission this week. When sports betting went live, the MGC made it clear to DK and every other mobile sportsbook that credit card deposits are not allowed in the Bay State. Thanks to human error and protocol mistakes, DK indeed took credit card deposits and allowed bettors to use those funds.

DraftKings told the MGC it was a misunderstanding, which they didn’t seem to buy. They proceeded to hand down “the largest (fine) for a gambling violation against any gambling operator ever issued in the state, and is among, if not the, highest meted out to a wagering platform anywhere in the U.S. since the Professional and Amateur Sports Protection Act (PASPA) was overturned in 2018.”

Jill Dotson of InGame has all the details of another example of the MGC not messing around when it comes to sports betting in Massachusetts. The MGC does not mess around.

And with that, I believe we have said it all. I’ll have some Saratoga Whitney Day ideas tomorrow on X.com - it looks like a great card, and I wish I could be there. Good luck with all your bets there and elsewhere if you’re playing.

And thanks for reading.