Jay Cutler Blind Taste Tests Four Bourbons and Yes, Four Roses is His Favorite

by Amy Myers

Four MVP bourbons, one MVP quarterback – Jay Cutler and Outsider’s Brandon Chesbro took part in a blind tasting and demonstrated just how well they know their dark liquors. Recently, Outsider has been keeping tabs on its own Final Four lineup, slowly whittling down the best brand names in the country. Now, we’re letting a couple of professional whiskey lovers cast their votes in the matter.

During Outsider’s Final Four tasting lineup, Cutler and Chesbro had to discern the difference between Four Roses, Woodford Reserve, Buffalo Trace, and Eagle Rare – a tough choice for anyone to make. These are some of the most well-loved bourbons in the world, and while they all have their shining qualities, there’s something to be said about a best-all-around kind of drink.

All four choices are viable contestants for the top of the leaderboard. While Woodford Reserve boasts light notes of citrus, cinnamon, and cocoa, Buffalo Trace has flavors like brown sugar, spice and oak, toffee, dark fruit, and anise. Eagle Rare gives off hints of candied almonds and very rich cocoa, and Four Roses leaves sippers with fall, fruity flavors like pear and apple.

So, which ones Cutler and Chesbro will pick is just about anyone’s guess.

Jay Cutler and Outsider’s Brandon Chesbro Try out Social Media’s Favorite Bourbons

Buffalo Trace Versus Woodford Reserve

First up was Buffalo Trace versus Woodford Reserve. After taking a sip of water to clear his palate, Cutler was first to take a sip from his testers.

“That’s Four Roses,” the former Bears QB said confidently.

Chesbro, on the other hand, wasn’t so sure.

“That’s Buffalo Trace, and that’s Woodford,” he said.

Sure enough, that’s exactly what the two bourbons were. Chesbro managed to guess his bourbons correctly without looking at their labels, a tough skill to master. Perhaps he picked up on those richer flavors in Buffalo Trace and the citrus notes in Woodford Reserve.

After trading a well-deserved fist bump, both Cutler and Chesbro cast their votes for Woodford. And so, onto the next head-to-head they went.

Four Roses Versus Eagle Rare

Of course, after whittling down the blind taste to only two other options, this round was a bit easier. But when you have four bourbons lined up in front of you, it’s hard to pinpoint those small but crucial differences in the nose, flavor and finish.

“As much Four Roses as I drink, I should probably know this, but I don’t,” the Bears QB said after sipping from the final two glasses.

Then came Chesbro, the champ again.

“That’s Eagle Rare. That’s Four Roses,” he said, pointing from left to right.

After some thought, Cutler agreed, this time sure he identified his favorite bourbon.


Obviously, we know which hat Cutler’s throwing into the ring. And even better, Chesbro chose the same bourbon.

For our line-up, that means that Woodford Reserve is up against Four Roses in the final tasting. And something tells us it’s going to be a tough choice…

Follow along on socials and cast your vote for most loved on Outsider Instagram and Twitter.