Sid Rosenberg Talks NFL and Betting With Jenny Woo

Written by:
Jenny Woo
Published on:
Sid Rosenberg

I had the opportunity to sit down with a guy that a lot of you may know.  Sid Rosenberg has been a true icon on radio and TV stirring things up on shows like Imus in the Morning, WFAN radio in New York, CBS Sports Line, and The Howard Stern Show.  We sat down over lunch after his photo shoot for his new book coming out next March.  As we reminisced on the great turnout at the VegasInsider.com Sports Handicapping Seminar, we also talked candidly about the ups and downs of his career as well as his achievements along the way.   

JENNY:  How was your overall experience at this year's VegasInsider.com Sports Handicapping Seminar?

SID:  This is my second one in the last three years.  I didn't go last year.  I went to the one two years ago and I went to the one this year.  I thought this one was the best one and that we had the best roster of handicappers.  What they did this year to the years prior is they condensed it.  Before, there was an extra day and there were more seminars.  This year, the theme was more quality than quantity; which I like a heck of a lot better.  We did four on Saturday, four on Sunday.  I think we did eight in all and they were better.  We also cut down on the time.  At least when I moderate, I try to make sure that it gets done pretty quickly.  Ideally, ninety minutes is about as long as you want to go and even that is long for certain seminars.  But for the NFL and College, you want to go about ninety minutes.  So I thought between condensing the days, maintaining the right time for each seminar, the roster of handicappers and the people out there - I thought this was by far the best job that Vegas Insider has done.  The handicapping seminar was the best it's been.

JENNY:  Isn't it true that they sized down the amount of handicappers to only have the best of the best at this year's seminar?

SID:  Yes and we had a lot of guys out there a couple of years ago that are just - I'm not going to disparage anybody - not very good.  (Haha)  Peter decided this year to get the best guys, the guys who are most in sync, the guys that are most to the point and the guys - quite frankly - who've had a lot of success.  Of course, at the end of the day, those are the guys that sell.  Right?  You go onto the website and see this guy's won sixty three percent of the time.  Well, you're going to want to go to Vegas and listen to that guy's philosophy because obviously he's successful.  So guys who haven't done well in the past, who were showing up for a free weekend in Vegas, we didn't need them this year.  Pete condensed the roster to the guys that either sell or - at the very least - the ones that don't sell all that much have very good reputations.

JENNY:  You spoke on the panel and were also a moderator this year.  Can you give our readers an outlook and predictions on what you expect this football season?

SID:  I did moderate the College and the NFL forecast.  I think in the NFL - at least when I go back and take a consensus of what the guys said on the panel - they're pretty convinced that the San Diego Chargers are going to represent the AFC in the Super Bowl.  I'm not - I like the Patriots.  Tom Brady is back.  I know he's kind of limping around a little bit.  He doesn't look great - he looks great but football wise he doesn't look great.  But I like the Pats.  The consensus on the panel was San Diego because they play in a weak division in the AFC West.  Kansas City is not good.  Oakland has improved but they're not good.  Denver is on the decline.  They like the Chargers. 

In the NFC, I like the Eagles, which pains me to say that because I'm a Giants fan.  I think the Eagles' players, the organization, and the fans are the biggest scumbags in the history of any professional sport.  F**king scumbags.  I hate them.  I hate them but they're good.  They had a really good off-season and they had a really good draft.  They've brought in Michael Vick who I think will pay dividends down the road but to be honest I think it'll be a little bit of a disaster.  But I think they're the best team.  Yet, the guys on the panel seem to lean more - there are a couple of guys that like the Minnesota Vikings.  Brett Favre is there now.  That's (Minnesota Vikings) a pretty good football team.  But I think the consensus is the Eagles.  So the guys on the panel are for Eagles vs. Chargers to represent Super Bowl this year.  I like the Eagles vs. Patriots. 

College football - everybody loves Florida.  Tim Tebow is back.  They won the championship last year and odds are they're going to win it again this year.  They lost Percy Harvin; he's a wide receiver and he got drafted by the Minnesota Vikings.  But for the most part, the team is in tact.  Tim Tebow is the best player in college football.  That seems to be the consensus for one of the teams to play in the national championship.  The other seems to be Texas.  They have a great quarterback in Colt McCoy.  He comes off a phenomenal season and he's had a couple of good years of a background with Texas.  The people that stayed away from Texas were the people that were worried they have to play inside the Big 12 where you've got Oklahoma and Oklahoma State.  You have tough competition in that conference.  Certain people still talk about USC, even though their quarterback last year, Mark Sanchez is now a starter for the New York Jets.  So there's quarterback questions at USC.  Some people like Penn State coming out of a Big 10.  But I think for the most part, the consensus is Florida will play Texas in the national championship and I tend to agree with that. 

JENNY:  How long have you been handicapping and how long have you been involved with VegasInsider.com?

SID:  I've been betting sports since I was 10 years old - unsuccessful mind you.  (Haha)

JENNY:  (Haha)  Let me rephrase that then.  How long professionally and legally?

SID:    I bet my first teaser bet when I was 10.  I'll never forget - I had St. Johns in a college basketball game.  I loved St. Johns back then and they screwed me.

I want to say that I hooked up with Vegas Insider four years ago - maybe.  I have a great relationship with Peter.  He's a friend of mine.  Marc Mariani - he's a guy that was involved with VegasInsider.com - I worked for him at CBS Sports Line ten years ago.  I'm more of a sports enthusiast, a radio host, a TV host.  I know everything about the sports.  I don't know anything about gambling.  But I can tell you every roster of every team.  I can tell you how they faired the last 10 years.  There are guys up there that don't know anything about the team but they have great records because they have all these trends and analysis.  I'm the guy that knows everything about the teams.  Sometimes that translates into big threes, sometimes it doesn't.  But I've done it for about four or five years and I started on VegasInsider.com; that's the only site that I pick games for.  Nobody else.  

JENNY:  With all the information via the Internet - do you see a lot more squares trying to pass themselves off as a pro?

SID:  Yeah.  Basically, anybody who's out there that thinks they know something about football - all of a sudden they're a pro.  I know guys who walk into Peter's office and he'll say, "What's your winning percentage?"  And the guy will say, "Seventy-five percent."  And he'd be like, "Get the f**k out."  Because nobody is seventy-five percent right.  Nobody.  But guys walk in and go, "I think fifty-three percent last year.  I think fifty-two percent this year."  That guy has a better chance of getting a job because now he's being more realistic.  There are a lot of guys out there - nerdy sports guys - some of them we have on our roster at VegasInsider.com that their whole lives are sports.  They'd rather win a football game - quite frankly - than be with a beautiful woman.  I'm serious.  So we have some of those guys and they think because they know a thing or two about the game that they're going to win their bets.  But it doesn't always translate into that.  Sometimes the more you know, the less you win.

JENNY:  What do you think of Delaware and New Jersey's efforts to legalize sports betting?  Will it help your business?  Do you see this as the new trend - legalizing sports betting and potentially ONLINE sports betting at the state level?

SID:  Yes, yes, yes.  I think Delaware is going to come through and that it's going to get done.  I was talking to Chad Millman from ESPN on the panel on Saturday and he was convinced it was going to get done.  He wasn't sure exactly what type of bets you were going to be allowed to make in Delaware but you would be able to bet legally in Delaware.  That's right around the corner.  I think it is good. 

Look, I often say this, there are three things in life we're always going to do that they should legalize.   You gotta legalize marijuana.  You have to.  Now, I'm not an advocate of people driving while they're smoking marijuana - just like I'm not an advocate of people driving while they drink liquor.  But you have to legalize marijuana. 

You gotta legalize prostitution.  You have to.  These girls who are out there getting beaten up by their step-fathers and fathers; who run away when they're 10 years old and have no where to go, end up hooked on drugs and getting beat up by these low life pimps.  We gotta give these girls healthcare.  Look, men are going to have sex.  It's not going to go away.  So clean these girls up and give them a chance to have some type of self-respect.  I'm not talking about the high priced escorts in Vegas.  I'm talking about ninety percent of prostitutes in this country are runaways or drug addicts or girls who were molested.  Give those girls a chance. 

The third thing is betting.  People are always going to gamble.  I said this on Saturday but a buddy of mine was a bookmaker - he went away for a long time.  He always said to me, "If they wiped out every bookmaker across this country, the ripple affect - because of the cash taken off the street - would be more catastrophic economically than if Wall Street collapsed."  And he's right.  That's how much gambling goes on every single day. 

JENNY:  People gamble on everything.

SID:  Everything!  Listen Jenny, you could bet now on the winner of Dancing with the Stars.  So why not make it legal; why not tax it; why not let everybody share in some of the wealth.  Instead, you have people living in America that have to bet through Costa Rica.  Its just nonsense.  I think they will legalize it in Delaware; I think it is a new trend and eventually we're going to get to the point that we're going to have a lot of states with gambling.  I think it's a good thing.  Legalize marijuana, prostitution, and gambling. 

JENNY:  Do you constantly involve yourself with sports politics or even just politics? 

SID:  More politics than sports politics because of my Imus connection.  I was on the Imus morning show (Imus in the Morning) for so long and that is a political show.  I used to do nine hours a day at WFAN in New York.  I was on the Imus show for five hours and then I had my own mid-day show.  My mid-day show was a sports show.  We talked about the Jets, Giants, Mets, Yankees.  But the Imus stuff, I would sit in the studio with John McCain and George Bush.  You name it,  I met them.

JENNY:  Were you the one that would ask those difficult questions that people wanted to ask but couldn't?

SID:  Every now and then I would do that.  Things that Imus wouldn't ask because he was still the guy that was trying to maintain this image - this persona.  Even if Imus was thinking it - he's like, "That's why I have Sid here.  That little degenerate kid over there, he's going to say something to Bush that's really going to piss him off."  (Haha)  So I did do that.

JENNY:  I could see you doing that too.

SID:  I loved it.  I spent as much time - I don't watch games at night - I don't have a TIVO because I don't watch whole shows.  I take my remote and I go back and forth.  I'll go back and forth between a baseball game and football game but I'll spend just as much time watching Countdown with Keith Olbermann, Chris Matthews, O'Reilly - I watch them all.  I am equally as interested in politics as I am in sports.  

JENNY:  You had a photo shoot today for your book - which you look good by the way.  Tell our readers about your book and when and where will your book be available.

SID:  It's a funny thing.  I had a huge book deal with a six figure advance that was ready to go back with Hyperion which was a huge publishing house (it's owned by ABC) back in 2004 and I got fired from the Imus show.  So they cancelled the book deal.  Then a couple of years ago, Simon and Schuster came calling and I signed a deal with them which was also a huge advance.  Then, I was on the air the day that Imus pulled that whole Rutgers stunt - it was me, Imus, and Bernie (Bernard McGuirk) - I was on with them at the time.  Everybody got fired and Simon and Schuster took their book deal off the table.  So this is actually my third book deal in the last four years with a publishing house.  It's Triumph Books.  They're the largest sports publisher in the country.  The book though - unlike most other sports books which are just kind of lists and sporting events of who has more runs and more touchdowns - is going to be more of my sports opinions, my sports experiences working at WFAN in New York and radio down here, some of the Super Bowl parties I went to, and some of the people I met along the way.  But this book also opens up into my personal life because part of my career has been with controversy - the drugs, the drinking, the gambling, all that stuff.  I've been suspended many times, fired many times, always ended up on front of the New York Post or Daily News.  I had a very controversial career and that's going to be in the book as well.  But I'm going have athletes, broadcasters, and entertainers remark about their relationship with me, how they're similar to me and how they're not, how my philosophies and lifestyle affected them, and guys like Pat Riley, Lawrence Taylor, Tiki Barber, Jerry Seinfeld, and Jim Nantz - it's all in the book.  When I try to describe the book - I used to work with a guy named Chris Russo, he's on Sirius XM now; his nickname is Mad Dog - of Mike and the Mad Dog Show.  His book was a sports book.  So you take his book and you have a head on collision with my friend, Artie Lange (who wrote a chapter for my book) from The Howard Stern Show.  His book "Too Fat to Fish" came out last year, which is about his drugs and drinking.  If you had a head on collision with Chris Russo's "The Mad Dog 100" and Artie Lang's book, you come up with my book; which will be good because people can identify with not just the sports stuff but also the every day life stuff that quite frankly ruined my career and personal life many times.

JENNY:  When is it planning on coming out?

SID:  March. 

JENNY:  Where will it be available?

SID:  Everywhere - Amazon.com and bookstores.  Right now, I'm slated to do a four city book tour.  They're looking at New York and Miami for sure - obviously.  But Boston and Chicago are a maybe as well.  Right now, it's certainly New York and Miami.  It'll be in Amazon.com, Borders, Barnes and Nobles in New York.  We're not done with it until October 1st and hopefully it'll be all over the country.  

JENNY:  Currently, do you have your own radio show?

SID:  I don't right now.  But I just signed a multi deal last week with 560 WQAM-AM here in Miami.  It's the home of the Dolphins and the Hurricanes.  It's been around a long time and I start there exactly 2 weeks from today - Thursday September 10th, 10 am - 2 pm.

JENNY:  Are you excited?

SID:  Yes, I'm very excited. 

JENNY:  You're ready to get on the radio aren't you?

SID:  I like my job.  I've been paid very well for it.  If I hadn't f**ked things up, I could have been the biggest star on radio in New York now.  In New York, which is the number one media market in the world, if I hadn't f**ked things up - I had it.  But I've done well down here, I like it here, and I like my job.  So four hours a day, I'm going to replace Neil Rogers who was a legend here for 33 years, a guy that's actually up for the Radio Hall of Fame this year.  I'm going to take that time slot starting in 2 weeks.  I'm ready to rock and roll. 

JENNY:  What's the memorable moment you've had in your career?  I'm sure you've had many but which one comes to mind?

SID:  I would think President Bush.  The athletes are great - like I mentioned earlier - Lawrence Taylor, Joe Montana, Joe Namath.  At one point - because I worked at CBS Sports Line - I've interviewed Pete Sampras, Tiger Woods, Shaquille O'Neal, Michael Jordan, Wayne Gretzky, Alex Rodriguez.  But what I find in this business is that often times the bigger the name the duller they are because they're so worried - because they're such a big name out there - about their persona that they keep it nice and mellow.  I had the opportunity back in 2004 - the Republican National Convention was in New York at Madison Square Garden - Imus was away because during the summers he spends his time at his ranch out in New Mexico.  We would do the show from New York and he'd be on the TV screen out in New Mexico.  President Bush Sr. - not the dopey kid who just left office - but the father is actually very smart and I like him.  He came into the studio that day and Imus was away, so I was supposed to come in and do my sports updates on the Imus show every thirty minutes.  To make a long story short, the guy who ran the station said, "Sid, come in the back, somebody wants to meet you in Imus' office."  And I said, "Okay."  I had no idea what was going on.  I walked into the office and it's President Bush.  And he goes to tell me that him and Barbara watch Imus every day and that I'm the favorite part of the show.

JENNY:  Really?  That's awesome.

SID:  Yeah.  I'm telling you that I had said some awful things about his son and his daughter-in-law - just awful stuff but he took it with a grain of salt.  He took it as, "That's this kids roll - to stir it up." 

JENNY:  Well that's part of being President.  You have to take some of the lashing.  (Haha)

SID:  Right but he was cool about it.  I was killing his kid.  He was like, "Barbara and I love you."  And he started to go over stuff in the office that I had said in week's prior.  You see, people who say "I love you" on the air, that doesn't mean that they've heard me once.  But when the President sits down and says, "Remember when you said this three weeks ago?"  I'm going, "Holy sh*t!"  Then we sat for thirty minutes and talked about the Texans, David Carr, the Houston's football team, the Astros, and the Texas Rangers.  I spent 30 minutes with President Bush.

JENNY:  That candidly?

SID:  Like you and I are right now.  He then went on the Imus show thirty minutes later and Don (Imus) asked him what he was doing back there.  And he said (Bush), "Oh, I was talking to Sid."  Imus said, "I'm sorry about that.  That f**king kid."  Then Bush said, "No, I loved it.  I love that kid." 

I've gone and spent time at the golf tournaments and met Bill Clinton and the rest of those guys but to spend time like that with Bush (Sr.) was pretty amazing. 

JENNY:  What has been your biggest achievement to date?

SID:  This - right now - you and I.  (Haha) I would still think the WFAN thing.  I never took a communications class ever in my whole life.  Never did college radio; never did high school radio; never took TV radio classes.  Here I was in 1997 fresh out of rehab, working as a waiter at L&N Seafood at Town Center Mall in Boca Raton and literally three years later I was on the Imus show hosting the mid-day show at the number one station.  Guys worked forty - fifty years to do an update in New York, let alone own nine hours of real estate every single day.  That's probably the reason why I think I blew it was because I don't think I ever appreciated what I accomplished or what I had.  I didn't grow up as a kid who wanted to be a sports radio guy.  It just fell in my lap.

JENNY:  Do you think the reason why you became so popular in such a short amount of time was because of who you are and you personality and they loved it?

SID:  Yes or they hated it.  Howard Stern and everybody else taught me a long time ago - they'll love you or hate you but just as long as they listen.

JENNY:  Well I guess Howard Stern is one to prove it.  Some people hate him but they can't stop listening to him.

SID:  Exactly.  I would say it's 50/50.  Fifty they love me and fifty they hate me.  The guys that you know what they're going to say next - they'll listen to those guys.  People can say, "That guy Sid's an a**hole but when he said this."  Or, "That guy Sid, every time he says something that's exactly what I was thinking."  That's where you want to be.  You want to loved or hated.  Every single day I come off the air and I say, "Did I say something today that's going to make people love me or hate me?"  Then it's a good show.

JENNY:  As far as achievements, when your book comes out, do you think that'll be on your top ten achievements?

SID:  Oh yeah. 

JENNY:  Maybe top five even?

SID:  Maybe top three.  (Haha)  Maybe two.  It's just an amazing thing.  Again, it's not with me yet so I can't appreciate it now.  I spend an hour on the phone with my author up in New York every day.  I tell him a story and he's going to jot it down because he's writing the book.  He writes for the New York Post; he's a very good writer.  I think when I actually walk into a Borders and see my face on a f**king book cover, I think it's going to be pretty surreal. 

JENNY:  And of course there are going to be people to criticize that as well.  (Haha)

SID:  Oh there's no doubt.  There'll be people who say, "He didn't say enough."  And then there'll be people who say. "Whoa, I don't know about all that."  Then there will be people who say, "I gotta give the kid credit.  He put it out there."  Some guys shy away from that acting like things never happened but I'm not doing that here.  It happened and I'm compelled to talk about some of it.

JENNY:  Thanks Sid.

SID:  You're welcome. 

Jenny Woo, Gambling911.com Senior International Correspondent

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