Friday Four-Pack 7.4.25

It's a podcast IN a newsletter as The Big O talks Celtics. Sox keep spinning. Sports bettors lose bigly with the OBBBA. MutStack Notes!

Professional spinmaster Sam Kennedy was at it again on Thursday.

The Red Sox CEO was asked on WEEI if the team would be big players at the MLB trade deadline, and if they had the blessing from ownership to add salary to improve the team.

“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.”

Kennedy was on both WEEI and NESN this week. Chief Baseball Officer and fan of big words, Craig Breslow, also made the NESN rounds this week. He even had a 40-minute conversation with Underdog’s Jared Carrabis, though it was not recorded. Too bad. I’m sure Breslow tried to convince Carrabis, like Kennedy is trying to convince the fans and media, that the team is committed to winning this year and will go all out at the deadline to make the team better. That, despite trading their best hitter, they’re contenders for the World Series.

I don’t believe them. You shouldn’t either.

They have lied to you repeatedly. Two years ago, the team promised and then failed to deliver on a “full-throttle” offseason. Just this season, Kennedy appeared on NESN and said that when the time was right and the moment was big, Devers would play in the field for the team. Forty-eight hours later, he was traded in a deal that was clearly a salary dump.

“I don’t think you can say that when Raffy Devers leaves the middle of your lineup, that specific move makes you better... We made the move for baseball reasons that were necessary. We’re confident in the group that we have,” Kennedy said Wednesday, again on NESN. Awesome!

So why are they doing this? Why do they keep lying to their fans?

1. They think you’re stupid.

2. They’re desperate to keep you watching the team and going to Fenway Park.

The Sox are in D.C this weekend. Some of the players visited the White House and met with the President on Thursday. That made some fans and Red Sox podcasters pretty mad.

Anyway, they come home Monday night for the first of three against the Colorado Rockies. There are plenty of good seats available.

I searched on RedSox.com for 12 tickets, together, for Monday’s game. Perhaps you’re looking for 12 seats together. Well, I have good news for you.

You can find them in the Aura Club Pavilion 13, which sounds fancy. Or on the Green Monster (standing room, no seat). Or those cool RF Roof Box seats (again, standing room). Or Pavilion Box 14. And Pavilion Reserved 15. And 16. And 18. And 20.

Grandstand? Sure - sections 13, 14, and 27. And 3, 4, 5, and 20. There are many more; I stopped counting.

Those nice Terrace seats out in right field? You can have the whole first row, seats 1-12. Right Field Box? Sure. Beachers? Of course. Those Bleacher Terrace Top seats? Yep, those too.

In total, I found 41 different sections of Fenway Park where you can get 12 seats together for the game on Monday night.

The Sox have promoted Fenway as a destination for opposing fans, and it’s worked. There have been nights when the Yankees and Phillies have come to Fenway, and Sox fans sound largely outnumbered. But when shitty teams like the Rockies are here, you don’t get that visitor bump. The Marlins, A’s, and Pirates are all on the home schedule in August and September, which is not ideal for the team’s ticket sales.

Hence, the team’s early July sales push this week. They see what I see - a lot of unsold tickets for the next three months.

There is no reason to believe them when they make claims of adding at the deadline. And it’s easy to say now, because when and if the team falls out of it by the end of July and the deadline, they can use the standings as an excuse to sell rather than buy. “We were planning to buy, but….”

Their words - Kennedy’s in particular - are not to be trusted. He’s made too many hollow claims to be taken seriously at this point.

FanGraphs gives them a 16% chance to make the playoffs at this point, which feels about right. That leaves an 84% chance that the Sox miss the playoffs for a fifth straight season, and for the seventh time in the last eight years.

The good news is that there’ll be plenty of good seats for you and 11 of your closest friends to watch it all live at Fenway Park.

Meanwhile, this week’s newsletter is also a podcast, featuring a special guest talking Celtics. A bad, bad week for sports bettors. And we’re racing in Saratoga - I’ve got some tips for the people.

All ahead in this week’s Four-Pack.

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On ‘Ten with Glenn’…

Not surprisingly, there was a great response to former Sports Radio WEEI host and 2024 Massachusetts Broadcaster Hall of Fame inductee Glenn Ordway when he joined me for a MutStack Podcast late last year.

With the Celtics’ offseason being such a hot topic, I reached out to see if The Big O would join me for ‘Ten with Glenn” - the idea being a ten-minute podcast segment in the Four-Pack on the C’s and their plan for a ‘Gap Year’ this offseason. Glenn has been active on X.com, firing off posts about the Celtics, among other things.

I was never going to be able to contain Glenn to ten minutes, especially after Felger and Mazz randomly called him out by name on their show Wednesday for “carrying the Patriots water for all those years.” ‘Ten with Glenn’ was a dumb idea. I see that now.

So what you get instead, as part of this week’s Four-Pack newsletter, is a 40-minute video podcast with The Big O, who really should be in the Radio Hall of Fame as one of the pioneers of sports radio. It‘s heavy on Celtics, laughs, and some Pats/Belichick/Hudson/“Mut please get a real job” at the end.

Glenn is still wildly tied in, seems obsessed with Luka Garza, had high praise for Brad Stevens, and has thoughts on Tom Brady and Sydney Sweeney.

This was a lot of fun. ‘Ten with Glenn’ was a dumb idea, but The Big O was great.

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On Trump’s Big Beautiful Bill and Sports Betting…

It started with states raising the tax rate on sports betting companies.

In Illinois, lawmakers took it even further, adding 0.25 and 0.50-cent fees to each bet that sportsbooks in the state accepted. Not surprisingly, the major commercial sportsbooks DraftKings and FanDuel announced they would pass that fee directly to customers, in the form of a 50-cent fee per bet, starting on September 1, just in time for football season. Yes, you’ll be charged per bet in that state beginning this fall.

And now the federal government is also trying to reach into the pockets of sports bettors. Not just winning ones - but losing ones, too.

On Tuesday, the Senate passed President Donald Trump’s ‘One Big Beautiful Bill Act.’ If you’re surprised to read that last sentence in this stupid little newsletter, trust me, I didn’t think I’d be typing those words the week of the July 4th holiday. In the Senate version of the bill, a tax code change was proposed that will have a significant impact on America’s sports betting and gambling industries.

On Thursday, the House approved the Senate’s version of the OBBBA, making no changes to the updated sports betting and gambling tax code. It’s expected President Trump will sign the sweeping agenda bill Friday at 5 p.m.

And when he does, it could alter the landscape of gambling in the United States.

In plain English, the new provision says that starting in 2026, gamblers can only deduct up to 90% of their losses.

Under the current tax rule, let’s say you have $100k in gambling winnings and $100k in losses. Well, you didn’t ‘make,’ any money wagering, you broke even, so you won’t be taxed on your ‘winnings.’ Obviously.

Under this new provision, which says you can only deduct up to 90% of your losses, you now owe tax on an additional $10k of income. That’s because you’ve now won 100k but can only offset with 90k of losses. So, let’s assume a 25% tax rate; that’s a new tax of $2,500 on $10,000 you didn’t actually win.

According to multiple tax professionals, this would be for all forms of gambling. So sports betting, horse racing, DFS, and poker would all be included. I assume slots and casino games, too.

This provision could cripple professional gamblers. Let’s take the example above, but bump the volume up to $1 million in wins and $1 million in losses. There are lots of players in the gambling space playing that sort of volume every year. That player, under the new code, would be subject to a $25k tax on that $100k he or she, again, didn’t actually win.

Big winners will also be taxed more, since they can only offset 90% of their losses.

As for you, the casual bettor and loyal MutStack subscriber, this will likely not significantly impact your taxes. If you win enough to get a 1099-MISC from DraftKings, you’re going to have to pay on that anyway. But let’s say you win $10,000 betting on football in 2026, but lose $10,000 betting on football, DFS, poker, etc. Be prepared to pay a $250 tax on the $1,000 you never won. That annoying tax on fake income might be enough to push some casual bettors into other hobbies, or towards offshore and illegal sportsbooks. Professional bettors are already consulting with their accountants to determine if a move to an offshore is the best move for them.

So yeah, professionals and high-volume bettors/players get crushed here. Casual and recreational bettors will still be severely impacted, but not from a tax standpoint. From Jeff Edelstein, on what happens if this chases away the professionals and high-volume players:

“Betting volume drops: High-volume players cycle millions through sportsbooks. When they leave, so does that action. Odds get worse: Without sharp money helping to shape lines, sportsbooks will widen spreads and increase the vig to manage risk. Everyone pays more to play. Prize pools shrink: In DFS, remove the high-volume pros, and a $10,000,000 contest becomes a $10,000 contest. That’s not just bad for them. It’s bad for everyone chasing those prizes.”

All of that above in italics? That’s bad for us. Very bad.

Professional horseplayer Paul Matties is a very smart guy and does not seem prone to hyperbole, so this post was concerning. Many professional poker players have been echoing a similar message online over the past few days.

TL;DR Version: A new tax provision says that gamblers could still owe money to the IRS in years where they broke even or were slight losers. This doesn’t make any sense. It’s bad for bettors, and it’s even worse for states that planned to rely on sports betting taxes to fund their projects. Even if you’re a casual bettor, there will be an impact on the sports you bet on and the games you play.

Congresswoman Dina Titus of Nevada says she’s prepared to file a bill to roll back this provision as soon as this weekend. But once Trump moves forward, it doesn’t seem like there’s a real clear path to reversal.

The American Gaming Association supported the bill and then began hiding replies on social media because they were receiving a barrage of negative comments. Not a great look.

These new rules will take effect on January 1, 2026. And if they do, we’ll write about how we should all approach it as casual bettors next year. Detailed record-keeping and having a good accountant seem like areas we’ll probably start.

But even before this, betting on sports and winning long-term is hard; a lot harder than the fake touts on social media would have you believe.

A new provision like this - where even losing bettors can be taxed like winners - will make it even harder.

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On the opening of the 2025 Saratoga meet…

Trainer D. Wayne Lukas was a rock star. The Hall of Famer passed away this week at the age of 89. There he is, pictured above with Maggie Wolfendale, being interviewed after his 2024 Preakness winner Seize the Grey came back to capture the Grade 1 Pennsylvania Derby last September, paying $10.60 for every $2 you bet. Like so many Lukas winners over the years, he was a good price.

Lukas was ecstatic after the race, joining hundreds of partners in the MyRacehorse Stable for a winner’s circle photo so big, it had to be held out on the main track at Parx.

He was an excellent trainer, winning 15 Triple Crown races after coming over to thoroughbred racing following his dominance in the quarter-horse game. But ‘Coach’ was more than just a great trainer - he was great for racing.

In a time when most trainers are giving their horses fewer starts per year, Lukas continued to run his stable into shape. Anytime he entered, he was live, especially in a race that was devoid of early speed. And he was always ready with a good quote for fans and media.

He was a character in a sport that has had so many over the years. There will never be another like D. Wayne Lukas.

Jay Privman’s remembrance of Lukas is one of many tributes this week that are worth reading. I’m sure NYRA and most other racing jurisdictions will celebrate his life and impact in racing this summer and beyond.

🏇🏻 I'm thrilled there is racing in Saratoga this weekend. I'll be betting every day, the cards look great.

But yesterday was not Opening Day. Next Thursday is Opening Day. I can't and I won't celebrate Opening Day until then.

🏇🏻 The biggest ‘tip’ I can give people planning to bet Saratoga this summer comes in races going long on the dirt, usually a mile and an eighth. These races are historically dominated by speed. And in many cases, speed from the inside. People tend to want to bet closers at this distance, but you want to focus on the speed. Same goes for when they stretch out for a few races at a mile and a quarter and a mile and a half.

🏇🏻 The second biggest tip is for dirt races going a mile out of the Wilson Chute; inside posts dominate. This has been evident since the debut of the Chute a few years ago, but Ryan over at the very good Betting the Odds Newsletter did the work on the 2024 Saratoga meet, where 60% of the winners at this distance came from Posts 1-3. Speed, like 9-1 Raging Torrent in the Met Mile, proved to be very effective in the Belmont Meet at Saratoga in June. Rail good. Speed good. Rail + Speed = very good at this trip.

🏇🏻 As far as this weekend goes, I’d note that speed was pretty, pretty good Thursday at The Spa ^👀

🏇🏻 I’ll be happy when the new Belmont Park opens and there is less Saratoga. Less is more, even for the greatest racetrack on planet Earth.

As for things to do in Saratoga, my friend, the late Chuck Simon, compiled an awesome list a few years ago. Dairy Haus is a must-stop for our family every summer, and has a monster list of soft serve choices. And elite ice cream cake. Even after a losing day at the track, Dairy Haus hits.

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On your MutStack Notes…

💰We’ll get to this post in a second.

It was a busy week for professional athletes being investigated for ties to sports betting.

NBA Free Agent Malik Beasley was in talks with the Detroit Pistons on a 3 year/$42 million deal. Those talks are on hold as the FBI investigates Beasley on suspicion of “wire fraud, gambling, and prop bets.” ESPN reported on Thursday that Beasley was dealing with debt and had a range of financial issues. Not great.

Later Thursday, Cleveland Guardians pitcher Luis Ortiz was put on leave, as part of a separate gambling investigation. From ESPN:

Sources said betting-integrity firm IC360 sent two alerts in June to sportsbook operators regarding Ortiz, whom MLB has placed on "non-disciplinary paid leave" through July 17.

The first alert, according to sources who reviewed them, was sent June 15 and triggered by action on Ortiz's first pitch against the Seattle Mariners in the bottom of the second inning to be a ball or hit batsman. Ortiz opened the inning with a slider well outside the strike zone.

The second alert, sent June 27, referenced Ortiz's first pitch against the St. Louis Cardinals in the top of the third inning being a ball or hit batsman. Ortiz opened the inning with a slider even farther outside the strike zone.

Yes, you can bet on whether a pitch will be a ball or a strike on some sports betting websites. In this case, there was enough activity on those two pitches to flag Ortiz.

Here’s that second pitch that got flagged, which is the definition of a spiked slider. 👀👀👀. There are usually over 700,000 pitches thrown in a Major League baseball season, so these two being singled out seems significant.

We’ll see how it plays out, but especially in the Ortiz case, this is why legalized gambling is essential - you have these betting integrity groups looking for unusual betting activity and flagging it. Plus, you have the sportsbooks themselves doing their own work. Legal sports betting WORKS in protecting against events like this.

As for the above post, sarcastically pointing out that the NBA and other sports leagues are in bed with the sportsbooks…cut the shit. There is no connection between those marketing partnerships and millionaire athletes deciding to go ahead and do something they’re prohibited from doing. Like, somehow it’s hypocritical? Or not a good look? Dumb, dumb argument from people who are usually against sports betting, for whatever reason.

🏇🏻 It’s about time the New York Racing Association teamed up with Barstool Sports. I thought it was a little weird that Barstool hosted a huge live stream from the backyard at The Spa on Travers Day last summer (with some handsome guests) and NYRA didn’t make a real effort to promote it. Barstool, Dave, and Elio have given NYRA and horse racing huge promotion over the last few years. I have said for years that they are GREAT for racing. Teaming up to create special Barstool/Saratoga gear makes sense. This hat, in particular, is 🔥.

🏇🏻 Former Patriot Ted Johnson joined WEEI Afternoons this past January. He’s not full-time, as he joins the show an hour after it starts four days a week and does not work on Mondays. There is no chance that a former Patriot is not part of WEEI’s Patriots Monday shows in the fall, right? So, will he go full-time? There was not enough money in the budget to do that this year. Will there be other changes to free up money to make that move happen? Something has to give. Minor or major changes 2-6 PM on WEEI seem likely.

And with that, we have said it all.

July 4th is the second-best holiday of the year, behind only Thanksgiving. Wishing you and yours a happy and healthy Fourth of July. Stay hydrated. And good luck with all your bets this weekend.

Thanks for reading. And watching.