Loyalty is an expensive, annoying trap

I shared on Monday that over the weekend I was the proud recipient of $1,300 in Delta voluntary denied boarding compensation, and reflected on some of the possible consequences for the miles and points I'd budgeted for my upcoming travel.

Since I booked some speculative hotel rooms in Eastern Europe for next summer before the latest Club Carlson devaluation, but haven't booked our flights yet, I thought that would be a good place to see how far $1,300 in Delta transportation would get me.

The answer, it turns out, is pretty far! I was able to find this great itinerary flying into Prague and out of Frankfurt, for example, for $1,294, marketed and operated by Delta:

Since there are two of us going, I decided I'd use my Delta transportation voucher to fully pay for my ticket (since the voucher was issued in my name), then redeem FlexPoints or even SkyMiles for the other (if low-level award space opens up — fat chance!).

Silver Medallion status has (a few) privileges

Then I remembered: as a Silver Medallion, I get to choose Comfort+ seats within 24 hours of departure on Delta-operated flights for myself and companions flying on the same itinerary. If I book my partner and I on separate itineraries, I won't be able to select a Comfort+ seat for her without paying $129 for the outbound leg and $99 for the return.

Alternatively, I can book the two tickets on Delta's website, using the transportation voucher to cover the first $1,300 and paying cash for the balance. That would be way too expensive, even if I used my Arrival+ MasterCard to pay the the balance.

On domestic flights, you may or may not care about Comfort+ seating, but on two long-haul international flights, I don't think it's unreasonable to want some additional legroom in economy.

Loyalty makes easy decisions harder

I'll grant that this sounds like a corner case – a curiosity – and not a real problem. But in fact, I find myself in similar situations with some regularity.

Later this year we're flying to Portland to celebrate my partner's birthday. The flights I wanted cost $330, and were pricing out at 20,000 SkyMiles roundtrip. This is basically a wash: redeeming 20,000 FlexPoints would give me the equivalent of 3.33% cash back on $10,000 in spend, while redeeming SkyMiles would get me a 2.3% return on $14,285 in spend (since I earn 1.4 SkyMiles per dollar spent on my American Express Delta Platinum card).

Both returns exceed the 2.22% I'd earn with my Barclaycard Arrival+ MasterCard, so there's no wrong choice. On the one hand, my preference is to redeem SkyMiles as aggressively as possible, because of their rapidly dropping value. On the other hand, I'd like to keep my Alaska Airlines MVP status next year, and to do so I'll need all the paid Delta flights I can get.

So I split the difference: I redeemed SkyMiles for my partner's ticket, and FlexPoints for mine, for an average return of 2.72% on $24,285 in manufactured spend.

Here again, only I'll have access to Comfort+ seating, but additionally I'll have a free checked bag thanks to my Medallion status, while my partner will have to pile her firearms, knives, and dry ice into my bag in order to avoid Delta's checked bag fees.


Checked bag fees and charges for preferred seating are huge revenue sources for the airlines, and can be huge expenses for passengers willing to pay them. The free checked bags and preferred seats offered to elites are therefore real, tangible benefits of elite status.

But elite status also makes it easier to be guided by motivated reasoning, allowing you to justify decisions you wouldn't otherwise consider.

In my first example, Delta is presenting me with a false choice: buy a second cash ticket in order to secure my partner Comfort+ seating, or redeem Flexpoints for the second ticket and pay to upgrade my partner. It's a false choice because absent elite status we would both be fine sitting in Main Cabin seats!

In my second example, I'm redeeming valuable Flexpoints for my ticket instead of taking the opportunity to empty my SkyMiles account even further, all in order to earn a few thousand more Alaska Airlines Mileage Plan elite-qualifying miles.