The Greg Hill Show
The Greg Hill Show brings Boston sports and culture to life with sharp opinions, real conversations, and the kind of humor only New Englanders can appreciate. Hosted by longtime Boston personality Greg Hill, alongside co-hosts Courtney Cox, Jermaine Wiggins, Chris Curtis, and producer Chris Scheim, the show covers everything from the Patriots, Red Sox, Celtics, and Bruins to the day’s top stories in Boston and beyond. Expect lively debates, can't-miss moments, and regular appearances from big-name guests like Boomer Esiason, Mike Vrabel, Ty Law, Bill O’Brien, as well as Sam Kennedy & Craig Breslow from the Red Sox front office. Whether it's breaking news or unfiltered talk, The Greg Hill Show is the voice of Boston sports fans. New episodes drop Monday-Friday.
Episodes
Best Of Celtics on WEEI: Reacting to the 'Disastrous' Jaylen Brown Trade
WEEI presents a collection of raw reactions to the bombshell Jaylen Brown trade from The Greg Hill Show, Jones & Keefe, and Rich & Ken with Ted Johnson. The crew breaks down why this move leaves a massive void on the floor, tries to make sense of the financial implications, and dives deep into the metrics behind why the front office parted ways with the Finals MVP. That and more on this week’s Bes
7/2/28 - Full Show: Live from The Lobster Bar! | The Jay's Era has officially come to an end
HR 1 - What we're the Celtics thinking trading Jaylen Brown for Paul George?
HR 2 - Did the Celtics just trade Jaylen Brown for whatever at this point?
HR 3 - Could Jayson Tatum have kept Jaylen Brown on the team?
HR 4 - Front Office Report with Sam Kennedy | Hillnotes
HR 1 - Live from The Lobster Bar! | Celtics trade Jaylen Brown for Paul George and draft picks
Greg starts off the show pulling up to The Lobster Bar on a boat to join the rest of the crew to react to the blockbuster trade of Jaylen Brown being shipped to the Philadelphia 76ers for Paul George and draft picks. How bad of a trade is this and is this a fireable offense on Brad Stevens? It seems the only bright side of yesterday was that team U.S.A managed to advance in the World Cup.
HR 2 - Live from The Lobster Bar! | How concerned will Jayson Tatum be over Jaylen Brown being gone?
The crew continues the show at The Lobster Bar with questioning the Celtics potentially bringing in a new arena for themselves. They then dive into They Said It and wonder if the Celtics just gave Jaylen Brown for whatever they could at this point. They then take a listen to Brian Windhorst and do the Celtics actually believe Derrick White had a better season than Jaylen Brown. Wiggy then says tha
HR 3 - Live from The Lobster Bar! | Could Jayson Tatum have kept Jaylen Brown on this team?
The crew continues the show with Charlie Enright, CEO of US Sailing, and discusses his experience sailing and how Wiggy wouldn't want to get in the water. If Jayson Tatum had a say in the trade, could he have kept Jaylen Brown here and stopped the trade? Greg then opens the mic for guest leads and gets nothing but love from the people of Newport. And Mayor of Newport, Charlie Holder joins the show
HR 4 - Live at the Lobster Bar! | Front Office Report with Sam Kennedy
The crew wraps up the final road show with Sam Kennedy speaking on the Jarren Duran and Willson Contreras situations and if there is any chance Alex Cora comes back. Wiggy takes another crack at Wiggy 250! but he mixes up his historical events. Hillnotes then crush Brad Stevens and the Celtics for this trade. And Greg and the crew say goodbye as they finish off Road Show season 5!
Wiggy mixes up his historical events during Wiggy 250!
With some live flute music, Wiggy is put to the test with his knowledge on the Boston Tea Party, but he gets confused with another historical event.
Front Office Report: Sam Kennedy the situations with Contreras and Duran
Sam Kennedy joins todays front office report to speak on the situations with Willson Contreras and Jarren Duran, as well as if there is any chance that Alex Cora will rejoin the Red Sox.
Could Jayson Tatum have gotten Jaylen Brown to stay?
Could the Celtics have made this trade without the approval of Jayson Tatum? Could Jayson Tatum have stopped this if he wanted to?
CEO of US Sailing Charlie Enright joins the show!
CEO of US Sailing Charlie Enright joins the show and informs everyone on sailing and his experience sailing around the world. However Wiggy would not want to get into the water,
They Said It: Chris Mannix says the Celtics trade was a wild trade
They Said It kicks off with Chris Mannix's reaction to Jaylen Brown being dealt to Philadelphia. Did the Celtics just decide to trade Jaylen Brown for whatever they could get at this point?
Are the Celtics going to be getting a new arena soon?
Will the Celtics be getting a new arena soon? What's the reason for bringing a new arena in for themselves. Even though everyone may be upset about the trade, the 4th of July is still right around the corner for us.
Jaylen Brown has officially been traded to the Philadelphia 76ers
Jaylen Brown has been traded to the Philadelphia 76ers, what were the Celtics thinking about this? Does anyone agree with it? Wiggy says this was a complete moron move Brad Stevens.
Greg aura farms on a boat on his way to The Lobster Bar!
The crew kicks off the final road show from The Lobster Bar in Newport Rhode Island and Greg pulls up with a grand entrance to get ready!
7/1/26 Full Show - What is the direction for the Red Sox and Celtics?
Hour 1 - Well, the Red Sox win streak was fun. What now for them?
Hour 2 - How do other players view the Brown situation? They Said It!
Hour 3 - The News and another edition of Wiggy 250!
Hour 4 - Have the Jays underachieved together and where does the team go from here?
HR 1 - Do you believe the Celtics have a plan?
Hour 1 - It was fun while it lasted but the Red Sox win streak is over. How did day one of NBA free agency go? Do you believe the Celtics have an actual plan now that they have whiffed on Giannis?
HR 2 - The Red Sox win streak was fun. Now what?
Hour 2 - Leads from Greg and Wiggy. Wiggy wants an extension for Willson Contreras and Greg is fascinated by new MK Ultra information. They Said It hears from Draymond Green, Chad Tracy and more! Could the sox have a reunion with Alex Cora?
HR 3 - The News | Wiggy 250!
Hour 3 - Mego gives us the news for the morning. Why 495 was closed down last night in Lowell. An update on the wedding of the century and more! Another edition of Wiggy 250!
HR 4 - Have the Jays underachieved so far?
Hour 4 - Was Willson Contreras's meltdown last night justified or do the Sox need to stop responding to all trash talk. What is the direction for Celtics, have the Jays underachieved and more!
Wiggy's ideal way to handle Jaylen Brown situation
What is the direction of the Boston Celtics now? Is Jaylen done here or will they repair the relationship. Wiggy shares his perfect plan for the rest of the offseason.
Do you have an issue with Contreras's actions?
The crew react to what Contreras did last night. Did you have an issue with him charging the mound and then responding to the fans on social media?
The News: Who gets builds a castle inside MSG to get married?
Do you believe the reports that the wedding of the century is taking place at MSG this weekend? Mego thinks this might be a ruse to distract everyone.
Wiggy 250: What does he know about FDR
Its another edition of Wiggy 250! Today Wiggy is asked to list off everything he knows about President Franklin Delano Roosevelt!
They Said It: Tracy defends Jarren Duran
During They Said It, the crew hear from Chad Tracy who explains what happened between Duran and a fan last weekend. Curtis doesn't understand why they keep defending this guy.
Wiggy wants the Red Sox to extend Contreras
Greg and Wiggy give their leads for the morning. Wiggy wants an extension for Willson Contreras and Greg brings up MK Ultra.
How much money was wagered on sports in 2025?
Leads from Scheim and Curtis. Scheim calls out hypocrisy from one golfer. Curtis asks how other NBA players view the Jaylen Brown situation. They react to the amount of money gambled on sports last year.
Red Sox win streak snapped
It was fun while it last but sadly the Red Sox win streak ends at 5. Was this the start of a turnaround for the season or a fluke win streak?
6/30/26 Full Show - Buying back into the Red Sox? | Brown done with the Celtics
Hour 1 - That's five in a row for the Red Sox!
Hour 2 - Checking the temperature on JB trade talks. They Said It!
Hour 3 - The News! Are the Red Sox players soft?
Hour 4 - Eliza Dushku joins the show!
HR 1 - Is the World Cup changing people's opinon on soccer?
Hour 1 - Yesterdays World Cup games were awesome. Scheim details his experience at the Germany game. Why do you think people are invested in the World Cup? Curtis wishes Tatum was more vocal.
HR 2 - Is Jaylen Brown fed up with the Celtics?
Hour 2 - Jaylen Brown is liking comments on social media that are negative towards the Celtics. Is he done with Boston, Wiggy believes so. The Sox have won five in a row, will they end up buying before the deadline? They Said It and more!
HR 3 - The News | Are the Red Sox soft?
Hour 3 - Mego gives us the news for the morning. Sewage water closing beaches, new developments in the Michael Proctor case and a fight over meatballs. The crew debate if the Red Sox young guys are too soft.
HR 4 - The next 11 games dictate the Red Sox future
Hour 4 - The crew are joined by Eliza Dushku. How she got into acting, her favorite roles and what she is up to these days. How is NBA free agency going to play out and can the Red sox make this season interesting?
Eliza Dushku joins the show! She's back in on the Red Sox
The crew are joined by Eliza Dushku. How she got into acting and her worst movie. How you can start helping out veterans dealing with mental health issues and now is the time to step up and help.
Wiggy 250: Gettysburg Address
In honor of 250 years of America, Wiggy is trying his best at American history trivia. Today he is asked to name everything he knows about the Gettysburg Address.
Do the Red Sox have too many soft playrs?
The crew debate whether or not the young guys on the Red Sox are soft. Wiggy says he refuses to judge another players injury and asks why no one is judging Crochet.
Does Roman Anthony want to get back out there?
Roman Anthony has finally spoken on his finger injury. Does he want to get back out there and are the Red Sox just a soft bunch?
They Said It: Bobby Marks doubles down
They Said it today hears from Paul Pierce and Bobby Marks. Paul Pierce defends Jaylen brown from unfair criticism and Bobby Marks doubles down on his Jaylen Brown criticism.
Jaylen Brown is liking Instagram comments... again
Greg and Wiggy gives their lead for the morning. Wiggy sees a world where the Red Sox end up buying at the deadline. Greg reacts to the comments Jaylen liked on Instagram.
Wiggy compares the World Cup to Nascar
Scheim is continuing to gush at how amazing the crowd was at yesterday's World Cup game in Foxborough. Wiggy continues to not care about the World Cup comparing it to Nascar.
Scheim's World Cup experience
It was an incredible day yesterday for World Cup soccer. Scheim was lucky enough to go and details his experience which leads to Mego and Wiggy calling him names.
Best Of Celtics on WEEI: Addressing the '7th Best Player' Report and Potential Jaylen Brown Trade Packages
WEEI presents a collection of discussions surrounding Jaylen Brown's future in Boston from The Greg Hill Show, Jones & Keefe, and Rich and Ken with Ted Johnson. The guys react to Bobby Marks' viral report that an NBA analyst considers Jaylen the "7th best player on a team," debate whether the Celtics' front office is leaning too heavily into analytics, and explore what a realistic trade market act
Best Of Red Sox on WEEI: Are Sox Reversing the Pivot After Yankee Sweep?
WEEI presents a collection of discussions about the Red Sox's four-game sweep of the Yankees from The Greg Hill Show, Jones & Keefe, and Rich and Ken with Ted Johnson. We debate whether a dominant pitching streak is enough to pause John Henry's "pivot" plans, plus trying to figure out if Jarren Duran's dramatic walk-off makes up for his ongoing issues with the fans. That and more today on Best Of
The Life And Times Of Roman Anthony | 'Baseball Isn't Boring'
Want to know what is going on with Roman Anthony? Listen to his latest sit-down with Bradfo. The Red Sox rookie goes into great detail regarding the injured finger that has kept him out of the lineup for almost two months, while offering an honest assessment of the challenges that have come with the absence. It's an important conversation with one of Boston's most important players. (There is also
6/29/26 Full Show - The Red Sox swept the Yankees! Can you Believe it!
Hour 1 - Somehow the Red Sox swept the Yankees. What does this mean for them?
Hour 2 - Will the Red Sox keep this momentum going? They Said It!
Hour 3 - The News! Wiggy tries his luck at American history trivia
Hour 4 - What are the Celtics going to do with Jaylen Brown? What's his value?
HR 1 - The Red Sox showed a glimmer of hope
Hour 1 - A miraculous weekend for The Boston Red Sox. They swept the Yankees at Fenway Park and they are giving us some hope. Scheim is in love with the trade the Bruins made this weekend.
HR 2 - Does this sweep change anything for the Red Sox?
Hour 2 - Will the Red Sox pivot on their pivot after the Sox sweep of the Yankees? Are you going to get sucked back in and what happened between Duran and a fan? They Said It and more!
HR 3 - What happened between Duran and the fans?
Hour 3 - Mego gives us the News for the morning. How a duck boat rolled over, yet another wrong way driver and a crazy debate about Cape Verde. The crew debate what happened between Duran and the fan.
HR 4 - How much value does Jaylen Brown have?
Hour 4 - Are the Red Sox still competing for a wild card spot or should they still sell? What should the Celtics do with Jaylen Brown? Is it the best move to trade him or should they hold onto him?
What are the Celtics doing with Jaylen?
The crew still have no idea what is happening with Jaylen Brown. Is he going to get traded, is he going to stay, nobody knows! Is there a deal that you would take for Jaylen?
Should the Red Sox still pivot?
With the Red Sox sweeping the Yankees the crew debate if this will lead to management pivoting off of selling everything. Should they pivot or was this a fluke series sweep?
How well does Wiggy know his American history
In honor of the 250th anniversary of America, Wiggy tries his best at American history trivia questions. It goes exactly how you think it would.
Debate on how to pronounce Cape Verde gets wild
Mego starts to give the news for the morning. Another wrong way driver on the highway, and a shooting in Brockton after a World Cup watch party. Wiggy gets put on blast for his pronunciation of Cape Verde.
They Said It: Analytics say Brown is 7th best player on a team
They Said It involves the Brown's today. What Jaylen Brown's dad had to say about Stephen A Smith and Kendrick Perkins. Analytics guys in the NBA view Jaylen Brown has the 7th best player on a team... what!
What happened between the players and fans this weekend?
Leads from Wiggy and Greg. Wiggy refuses to be sucked back into The Red Sox after just one sweep. Greg wants to know what was happening between the players and fans at Fenway.,
The Bruins finally made a move!
It's been a quite few months for the Bruins but they finally made a move this weekend and Scheim is all for it. However he does have one issue with the Bruins.
The Red Sox sweep at Fenway!
What a turn of events, The Red Sox have swept the Yankees at Fenway Park! Is this enough o bring you back in or are you like Wiggy and need to see more?
Interviews of the week on WEEI: June 22-26
WEEI presents a collection of guest appearances and interviews on The Greg Hill Show, Jones & Keefe, and Rich and Ken with Ted Johnson from during the past week. Featuring Craig Breslow, Rob Bradford, Justin Turpin, Noa Dalzell, and Mike Florio.
Best of Celtics on WEEI: Will JB still be traded now that Giannis is off the table?
The hosts of WEEI don't hold back on the state of the Boston Celtics as trade rumors swirl around Jaylen Brown. They debate everything from Brown's cryptic "I love cats" tweet to whether Brad Stevens can find a suitable trade, and ultimately conclude that the relationship between Brown and the Celtics may be damaged beyond repair.
Best of the Patriots on WEEI: Why the Patriots might carry seven wide receivers this year
With Robert Kraft officially pushing the NFL for a regular-season game in Scotland, the Patriots' international future is taking center stage. Back home, the battle for the 53-man roster is heating up as we break down whether New England will actually carry an overcrowded room of seven wide receivers this season.
Best of the Red Sox on WEEI: It's time for Craig Breslow to blow up the roster
Red Sox Chief Baseball Officer Craig Breslow faces a rowdy, heckling crowd to address the team’s disappointing season, glaring mental mistakes, and upcoming trade deadline strategy. The crew breaks down the painfully awkward interview and debates whether the front office is completely delusional about the current roster.
6/26/26 - Full Show: Live from The Parrot! | Will the Celtics trade Brown before the season starts?
HR 1 - Is Jaylen Brown possibly a liability for other teams? | Bill O'Brien joins the show
HR 2 - Will Jaylen Brown even be back next season?
HR 3 - The News | Guest Leads
HR 4 - Patrick Dempsey joins the show | Front Office Report with Craig Breslow
HR 1 - Live from The Parrot! | Bill O'Brien joins the show
The crew starts off today's show live from The Parrot in Hull asking whether or not they want to see Craig Breslow with the Boston Red Sox. Even though the Tartan army has left Boston, Scheim doesn't let everyone forget about the U.S. in the World Cup. Is Jaylen Brown a liability to other teams looking to trade for him? Boston College football coach Bill O'Brien joins the show to discuss the excit
HR 2 - Live from The Parrot! | Will Jaylen Brown be back next season?
The show continues live at The Parrot with Wiggy expressing his excitement for a 24 team college football playoff bracket and Greg shares a study saying sunscreen may not be good for you. They Said It kicks off with Kevin O'Connor saying that the Timberwolves were exploring trades with Jaylen Brown. And Indiana Fever head coach Stephanie White goes off on how Caitlin Clark has been treated in the
HR 3 - Live from The Parrot! | Guest Leads question if Jaylen Brown could be traded midseason
The guys continue today's road show from The Parrot with The News that includes an accident involving a scooter and the guys question how dangerous scooters are and jellyfish are taking Boston! Greg then allows the people of The Parrot to give their own leads that include the possibility of trading Jaylen Brown mid season and if Stefon Diggs will come back or not
HR 4 - Live from The Parrot! | Craig Breslow joins todays Front Office Report
Craig Breslow joins the Front Office Report for today and discusses last nights win against the Yankees and if there was any disconnect with him and Sam Kennedy? Hillnotes make a reference with Scheim's drawn up routes he did for Bill O'Brien. Patrick Dempsey then surpises the crew calling into the show.
Hillnotes roast Scheim for his drawn up plays for Bill O'Brien
Hillnotes include telling Brad Stevens to get it together with Jaylen Brown and making a reference to when Scheim was drawing up routes for Bill O'Brien.
Front Office Report: Craig Breslow says there is not disconnect between him and Sam Kennedy
Craig Breslow joins today's front office report to discuss yesterdays win against the Yankees, whether he has had some disconnect with Sam Kennedy or not, and whether or not he believes the Red Sox will still win a lot of games or not
Guest Leads: Do you still believe Stefon Diggs could come back?
Greg allows for the public at The Parrot to give their own leads that include whatever they can think of about the Red Sox and one person asks if it's possible for Stefon Diggs to still return?
The News: Scooters are honestly quite a dangerous thing
The News includes Jellyfish population increasing in Boston, scooters becoming more and more dangerous, and Michael Proctor not showing up to court
They Said It: The Timberwolves were exploring a trade for Jaylen Brown
They Said It starts off with Kevin O'Connor stating that the Timberwolves were exploring a trade for Jaylen Brown. Would the return for Jaylen brown from Minnesota been good?
Wiggy is excited for the 24 team college football playoff bracket
Wiggy continues the leads with his excitement for a 24 team playoff bracket in college football, and Greg shares a report from science that says sunscreen could actually be bad for you.
Is Jaylen Brown seen as a liability to other teams?
With Jaylen Brown outside factors, could he be seen as a liability to other teams when trading for him?
We are live from The Parrot in Hull!
The crew starts off the show live from The Parrot about how the Red Sox pulled off a win yesterday against the Red Sox and the guys still say they want to see Breslow gone.
6/25/26 Full Show - Are you interested in shopping Jaylen Brown?
Hour 1 - Can the Celtics fix the relationship with Jaylen Brown
Hour 2 - Jaylen Brown coming after Stephen A again. They Said It!
Hour 3 - The News with Scheim. What is the biggest reason the Red Sox stink?
Hour 4 - Dianna Russini update. Waning belief in the Red Sox young guys
HR 1 - How can the Celtics appease Jaylen Brown?
Hour 2 - The Red Sox found a new way to lose last night and shame on us for being shocked. Jaylen Brown loves cats, what does this mean? How can they repair the relationship or will they sell him for spare parts?
HR 2 - Is it worth trying to fix the relationship with Jaylen?
Hour 2 - The show wants permanent 3am last call in the city of Boston. They Said It hears from Jaylen Brown, Marcelo Mayer and Don Sweeney. Is the relationship between Brown and the team fixable? Should they try to fix it?
HR 3 - The News | Biggest reason the Red Sox stink?
Hour 3 - Scheim gives us the news for the morning. How waffle house is getting sued, and an update on the wedding of the century. The crew debate the biggest reason why the Red Sox have no hope right now.
HR 4 - Russini update | Red Sox youth | Trade options for Jaylen
Hour 4 - The crew react to the latest update with Dianna Russini. They debate if the young guys will ever become what we hoped they be. Hill Notes are starting tp turn off the games and more!
Is it too early to bail on the young guys?
The crew debate why this Red Sox season has been horrible. Are the young guys to blame for this season and is it too early to bail on them?
What's next for Dianna Russini?
The crew react to the new NYT article about Dianna Russini? Did anything in the article upset or offend you? Wiggy wonders if she'll ever get another job.
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