This post will be less cryptic than usual, because it’s discussing a play that everybody reading this was at least aware of (and hopefully, you’ve been using it for the last few years). 

It’s time for the weekly reporting on the 2025 war on happiness, as Citi has finally decided to (likely) kill off the legendary Shop Your Way card, a bizarre partnership they had with all but defunct retailer Sears. 

I say likely because the card is discontinued and current cardholders will have theirs converted to some type of Citi Mastercard on November 3rd. However, nobody is 100% sure if the lucrative spending offers will continue or not. 

They have stuck through previous iterations of the card product, but the axing of the Shop Your Way program in general leads me to believe somebody at Citi that actually has a brain started looking into the P&L on these offers.

In case you didn’t have the card, the big draw was a never-ending parade of spend related offers that all stacked and mapped nicely to common MS categories. This past year, most of us with the card had multiple year long offers offering between 5x-10x cashback each month in certain categories, with 1-2 ad hoc offers per month that were generously open categories (i.e. “online shopping”) that stacked nicely with the year-long offers. 

If you had the card at the start of this year and qualified for the two yearlong offers, you likely profited somewhere between $5-$6k depending on how low you could get your cost and number of ad hoc offers qualified for.

It wasn’t a huge scalable play that will pay for your lime green Aventador, but it was essentially as easy as finding $5k on the ground, and especially spicy if you had multiple players. 

For a lot of us, the speculation isn’t “why did they kill it”, it’s “how did it possibly take this long?” – the offers were so generous, widely targeted, and again, stackable. It wasn’t uncommon to be earning 20% back on spend, which simply isn’t sustainable when the card had even become the darling of /r/creditcards. 

There was a theory that financially illiterate folks who were still clinging to Sears’ existence and carrying a balance on the card is what kept it afloat, but who knows – as of this post, there are only 5 Sears left in the entire world and even the most financially misinformed people know it ain’t coming back. 

Anyway, if this is the end, R.I.P. Shop Your Way card, a true unsung hero. 

But I promised that there would be hope for the future in this post too. As much of a bummer as it can be to conduct the autopsy on a dead play, the SYW one is kind of fun because it is the perfect example of what to look for in a lucrative play and illustrates some of the points I’ve made in what to look for in the past:

• A product involving an archaic legacy consumer brand? ✅
• A backend that seemed to be an even jankier version of an already janky backend? ✅
• A baffling mismatch between the motives of the marketing team creating the promos and the finance team responsible for the portfolio’s P&L? ✅
• Hell, even a little boost in +EV (via SYW points) that allowed you to treat yourself every once in awhile? ✅

While it looks like this may be the curtain call for a play that punched seriously above its weight, It’s a great example of what to look out for when probing in the future. I can think of a couple of live plays that share some of these characteristics, too. 

Until next time, y’all!