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Darren Rovell's Sports Tickets Collection & Betting the 2022 World Series

Written by: Bill Krackomberger
Updated October 27, 2022
9 min read

It’s episode 118 of Wise Kracks, and joining us this week is one of the most followed sports memorabilia collectors in America! We also talk about the 2022 World Series, a new low for Aaron Rodgers, the return of Dak Prescott, and this past weekend’s controversial UFC event. Let’s get it!

Your hosts Bill Krackomberger and Jon Orlando discuss the ongoing 2022 MLB postseason and who they think will be named the World Series champ. Will the Houston Astros or the Philadelphia Phillies take the title?

Green Bay Packers quarterback Aaron Rodgers will be a double-digit underdog for the first time in his career in his upcoming game against the Buffalo Bills. With multiple sportsbooks having him at +11.5, is this a good bet to get in on?

Dallas Cowboys quarterback Dak Prescott made his return over the weekend after being out with an injury since Week 1. Even with a 24-6 win against the Detroit Lions, the guys didn’t think he looked all that great on the field. Should the Cowboys stick with him?

UFC 280 is now in the books, and it was an event full of controversy and upsets. What do the guys make of it?

Joining the show this week is avid sports memorabilia collector Darren Rovell. He has also had stints at CNBC and at ESPN as the go-to for sports and business. He chats with the guys about the collectors market, the most obscure items in his collection, and making a sale that he regretted so much that he bought the item back in less than 12 hours. You’re in for a good time on this week’s Wise Kracks!

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Will Mattress Mack Strike Again with the Astros vs Phillies?

“The price gouging is out of control… the get-in prices for game 1 are over $900!”

Mere seconds into MLB World Series talk, Bill is already airing his grievances. With the 2022 World Series set to begin on October 28th between the Houston Astros and The Philadelphia Phillies, Bill and Jon are floored by how much people are paying for tickets to see the action. “People are paying $20k for tickets, it’s insane!” exclaims Jon. With that said, Bill knows where the real baseball fans will be, “Those prices take the fun out of it for true baseball fans… they’ll be filling up the bars in South Philly!”

However, ticket prices shouldn’t distract from the fact that there’s a great series of baseball ahead, and Jon has a hunch that the Phillies could take it. “Bryce Harper is possessed right now!” says Jon of the Phillies star.

With Bill, a little skeptical about some bets he placed, some being at Jon’s discretion, Jon reassures Bill that his money is safe. “I’ve had good predictions all season,” says an overly-confident Jon. Let’s hope for Bill’s sake that that confidence turns into cold hard cash!

With the World Series attracting bettors from across America, the guys discuss a couple of high-profile bets. One bettor placed $50 at the beginning of the season that could become $125k if the Astros beat the Phillies. Bill chimes in, “I guess it’s easy to look at now… he would’ve known a lot of teams weren’t going to make it.”

Even though Bill plays big bets, he knows that $50 is a lot of money for a lot of people. Even though this could be life-changing money for the bettor, Jon is cynical about the turnout, “At that amount… I don’t think he’s cashing that ticket.”

Another unlikely figure has risen to notoriety in the world of sports betting, and he’s known as Mattress Mack. the nickname of Houston furniture store owner Jim McIngvale, Mattress Mack has done very well placing large bets on the Astros over the last few years. As of right now, he’s bet approximately $10M on the team for this season alone.

Bill rolls his eyes, “I’m sick of hearing about it.” Jon scratches his head, “How was he able to bet that much?” With sportsbooks across the country, Mack likely flew from sportsbook to sportsbook betting as much as he possibly could. Bill nods, “He likely won’t get any money back if he loses it either.”

As sick as Bill is hearing of him, there is some good that comes out of the Mattress Mack situation, “Because of him, he’s influencing the lines and we’re getting value on our bets!”

Sports Tickets are the New Trading Cards

Our guest this week is Darren Rovell, a man who has more sports memorabilia than any kid could ever dream of. At 2 million Twitter followers, Darren shares his rare collectibles and sport takes with people that can’t get enough. Who can blame them; Darren was the go-to guy for sports business at ESPN for years before joining the Action Network in 2018. If there’s anyone who knows a thing or two about sports history, it’s Darren!

Darren begins with a perspective on collecting that Bill can hum to, “Everything is betting these days… collectibles, NFTs.” Bill gets it, “I guess that’s true, you’re hoping you get a good value on a card and you just never know!”

Darren was recently at one of the biggest memorabilia conventions of the year in Atlantic City, where he had tons of his collection on display. When Bill asks how much he sells, Darren responds, “I’m selling almost nothing.”

For Darren, his foray into the realm of collecting began when he was young, “I had always collected… at one point I thought I had gotten 17 autographs from Michael Jordan, but they were all fake and forged by his secretary!” 

With many of the items in Darren’s collection being one of one, he can control the market, “It has to be the price I’m willing to sell it at… the buyer won’t find it anywhere else!” That being said, however, he acknowledges that this creates an issue for collectors like him. With certain items being wholly unique, there’s no liquidity in the marketplace, “People have a hard time when they can’t compare it to something else.”

Although a lot of what Darren collects is sports related, his biggest sellers are often not, “Walt Disney autographs are the show stoppers.” He currently holds onto one of two Steve Jobs autographs to feature his signature inscription. He believes that he could make $150k off of it, which would provide him with a 20 to 40 times profit from what he bought it at, which is a typical margin for many of the items he sells.

Probably the most fascinating items in his collection are tickets to sports events. He explains why he tapped into this niche market, “Tickets are really scarce, so it’s always good to get your hands on them when you can.”

Some of his most prized collectibles are a ticket to Tiger Wood’s first PGA Tour event, which he bought for $2k and sold for $71k, a ticket for a Chicago Bulls game from 1984 in which Michael Jordan wore Air Jordans for the first time, and a 1994 NBA Finals ticket from the day of the O.J. Simpson car chase. Darren laughs, “I love the tickets that have obscure stories attached to them.” 

Of course, Darren doesn’t make the money he makes without graders defining his memorabilia’s value. Bill finds these practices a little suspicious, “These companies that grade stuff, I hear that if you have someone on the inside, you can do a lot better.” Darren responds, “These companies have become public companies, so they are looked at like NFL referees at this point!”

Darren outlines the grading process, “The more valuable your item is, the more you’re paying, so they’re more incentivized to give you a higher rating.” With different rates for varying turn-around times, and different grades that could vastly change the value of an item, the collectors game can be fulfilling, or a huge disappointment.

As deep as he is into the collecting game, Bill is curious about the amount of time he spends looking for things. “I spend about 20 hours a week canvassing auction houses and eBay… it’s not only a hobby, it’s a revenue stream.” Darren further concludes that it’s not something someone can just pick up, “You can’t write a program for this, it’s about understanding history.”

As the interview concludes, Bill has one more question, “Now that Sam Ehlinger is a starting quarterback for the Indianapolis Colts, do you think his signature will get better?” Darren lets out a huge laugh, “I jam on guys who have disgusting autographs! He has a little ‘s’ and a little ‘e’; what are you doing buddy? Any kid who got that would be disappointed!” PGA Tour

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Welcome to Wise Kracks, your one-stop-shop for betting, pop culture, tips & more! Your hosts Jon Orlando and Bill Krackomberger dive into the NHL, NBA, MLB, & NFL, while never forgetting to have a laugh along the way. 

A new guest joins the show every week, providing a unique insight into the world of sports and entertainment. Wise Kracks wants nothing but success for you, and Bill is here to show you the way. Tune into the WSN YouTube channel every Thursday to catch a new episode of Wise Kracks!

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Bill Krackomberger

Sports Betting Analyst, Content Specialist & On-Air Host

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Billy “Krackman” Krackomberger has made his living as a professional sports gambler for nearly three decades. You have seen him on ESPN, Gaming Today, and SiriusXM. His connections in the sports gambling industry run all the way to the top. His bets move the lines and regularly have him banned from books for being too sharp.
Nationality: American
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