Epic Rap Battles of History: Gary Leff Takes on The Points Guy at Frequent Traveler University

Here’s a list of battles by most casualties from Wikipieda.

Then there was Joe Frazier vs. Muhammad Ali, “The Thrilla in Manila”

And there’s my favorite epic rap battle of history, Abe Lincoln vs. Chuck Norris.

On April 28, we put all of those to shame.

The Frequent Traveler University schedule features Brian Kelly (a.k.a. The Points Guy pitted against me, in an epic showdown.

Resolved: that Delta Skymiles Offer Superior Value. A Debate Between Brian Kelly (Affirmative) and Gary Leff (Negative)

Will you be in attendance for this dramatic mileage battle? Will you be able to tell your grandchildren that You. Were. There.…?

  • Who has the better position here?

  • Who will win?

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

More articles by Gary Leff »


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  1. If i could get a decent fare to EWR from HNL, i would absolutely attend. Actually am more interested in hearing Steve Belkin’s remarks about elite status.

  2. This should be fun! And I will most definitely be in your corner rooting for you. Though I must admit, you have an admirable foe. Oh yes, I will be in attendance. But I didn’t realize the venue would be set up like a boxing ring!

  3. This fight isn’t fair… You have the upper hand! We’re talking about Delta Skypesos, not AAdvantage miles.

  4. “superior value” compared to what?

    I won’t be there, but I challenge Gary to show me another program where I can charge $12K to a credit card and get enough Skymiles for three round trip domestic low level coach award tickets.

    OK, since I know Gary prefers premium international awards, I still challenge him to find another program that for $25K in spend will give me two F round trips to ANC, 1 J round trip to Europe and 1 other F round trip within the US?

    If you can’t figure it out, come to the Chicago Seminars to find out how!

  5. I’ll be there too. But I am going to the alternative session as I don’t fly Delta! Now if you guys fight over American AAdvantage miles now that’s a different story…

  6. I had wanted to attend just to get info on this as there must be something I am missing.

    I have no clue how Brian Kelly is going to defend Delta. Everyone knows skymiles have very low value. They are only good for booking partner awards – and even then some of the partner awards such as Korean have many black out dates so you can’t book.

    The only thing I can think of is the credit card deals Delta has – except I think that is unfair, especialy to someone up north in Canada like myself where there is only 1 Delta card, and its not a particularily good one.

  7. > “offers superior value”.

    Superior to travel by tricycle, certainly. Today, I booked a domestic award one-way IAD-SFO flight for a mid-April Wednesday. I have enough miles to book this on all the majors so here were my search results. This includes partners and none had non-stop availability:
    United: 25k (mixed class booking, mostly coach.)
    Delta: 80k
    American: 25k with a stop in Texas.

    This included partners. It’s an unscientific study, but you could lead with three randomly chosen round trips and see how the rewards compare.

  8. I’m a big Gary Leff fan when it comes to extracting value and finding reasonable redemption In premium and much non premium travel
    I have also come to admire Brian very much over tbe past few years
    I think Brian has the tougher fight in a nut shell
    how in the world do you defend extract value from the Delta program when historically this remains perhaps tbe stingiest program ever for saver award inventory
    Yes there is some fair partner availability but how do you sustain a relationship with Delta and not get ripped off in the long run?

  9. Dear The Points Guy: “I’m clearly going for a sympathy win here!” LMAO! Hilarious!

    I really want to see this… If I’m in town that weekend I will totally be there!

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