As a former NFL general manager, Mike Tannenbaum has a deep understanding of how front offices are thinking, which is a valuable tool he brings to his work at ESPN as an NFL analyst. And on Monday, Tannenbaum’s expertise gave Cleveland Browns fans a sneak peek of what was to come later in the day when it came to second-string quarterback Kenny Pickett.
Tannenbaum appeared on Monday’s edition of the ESPN Radio show Unsportsmanlike, where he discussed the four quarterback depth chart of the Browns as we approach the start of the 2025 NFL season.
Most, including Tannenbaum, didn’t expect for the Browns to carry four quarterbacks entering the regular season. And this led to the former New York Jets GM to predict that Pickett would ultimately be the odd man out that gets traded prior to Tuesday’s league-wide deadline that makes every team cut down to a 53-man roster.
“It’s very unusual,” said Tannenbaum on the possibility of the Browns keeping four quarterbacks on their 53-man roster. “Ironically, they did do that last year. But just for context, 13 teams had three (quarterbacks), 18 teams had two (quarterbacks). Typically, you are seeing a lot of teams put one on their practice squad at this point. Look, it’s not impossible to handle your roster that way. But when you are rebuilding, and the Browns certainly are, you are going to lose a player you would otherwise be keeping. I still see Kenny Pickett getting traded. To me, that just makes too much sense.”
Tannenbaum would go on to add how there were several landing spots that made sense for Pickett to places where there have been quarterback injuries or inconsistencies at the backup position.
“Aidan O’Connell unfortunately gets hurt for the Raiders,” said Tannenbaum. “Joe Milton has been very up and down for the Cowboys, Cooper Rush left there. There are a number of teams that could use a veteran backup. And I just think that if the four of us are sitting here a week from today, I wouldn’t be surprised if Kenny Pickett was traded.”
.@RealTannenbaum joined @UnSportsESPN with @msmallmon @Arlenv1 and @CourtneyRCronin
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Listen back to the full interview via @espnpodcasts: https://t.co/sTjyT0siWu pic.twitter.com/TRwmWE3275
— ESPN Radio (@ESPNRadio) August 25, 2025
It turns out, it didn’t take a week for Pickett to be dealt by the Browns. Not only did Tannenbaum predict the Pickett trade the very same day it happened. But he also accurately predicted that the Raiders would be in the market for a backup quarterback in light of Aidan O’Connell’s injury.
On Monday night, ESPN’s Adam Schefter reported that Pickett had been traded to the Raiders for a 2026 fifth-round pick.
Kenny Pickett has now been traded from Pittsburgh to Philadelphia, from Philadelphia to Cleveland, and from Cleveland to Las Vegas. https://t.co/F2Wv29X3rS
— Adam Schefter (@AdamSchefter) August 26, 2025
Tannenbaum has certainly had his fair share of trade predictions that have come nowhere close to happening. But you certainly have to give him props for nailing this prediction within only a few hours before it came to fruition.