Why Both Cleveland Browns Kenny Pickett Trades Were The Logical Moves

During this Cleveland Browns roster building and contract preseason preview I will be covering everything from a General Manager perspective to get you ready for what the Cleveland Browns roster and practice squad will likely be week one.

At the start of the offseason, on the 10th of March the Cleveland Browns agreed to a trade with the Philadelphia Eagles to swap Dorian Thompson-Robinson and a fifth round pick for Kenny Pickett. Yesterday the Cleveland Browns dealt Kenny Pickett in a trade to the Las Vegas Raiders for a fifth round pick.

While some people will look at the deal as a round circle and say they traded a fifth and a player for a fifth it was a waste of assets and time, the team was in very different circumstances at both of these times despite it being the same offseason.

In this article I will look at the thought process of the front office on these two occasions to explain what was going through their minds and why the decision was made. This isn’t done from a hindsight perspective but what I was saying at the time of the first deal, all the way through.

The First Pickett Trade – Eagles

The Cleveland Browns traded for Kenny Pickett just before free agency opened. At the time the team had one healthy quarterback on the roster in Dorian Thompson-Robinson. If you are going to try and attract free agents then you are going to need more than a practice squad calibre quarterback to entice players to choose your team in an open market.

While they could have made their first addition in free agency as a quarterback, the position market tends to take a few days to come together, so they needed to look to the trade market for a quick solution. The only significant name of note was Kirk Cousins and no team wants to consider what Atlanta wanted in a trade across salary cap or compensation. If the Falcons would have cut him and he been available as a league minimum veteran, then he would have been a logical addition for the Browns as an alternative to Pickett.

Adding Pickett gave them a high quality backup quarterback who could been a competent bridge while the team searched for a longer term answer. He isn’t a player that will tend to win you the game but he showed with the Steelers that he can game manage and if everything else is going well around him, you can win.

At the same time you can continue to explore the free agency and trade market as players like Russell Wilson decide where they want to play the 2025 season.

With Pickett being a high quality backup he would always keep his value. John Dorsey traded the 65th pick in the draft and paid $16m for Tyrod Taylor, Pickett was far cheaper. The difference in talent between the two players is closer than most will realise. This meant the Browns could explore all options and then decide what to do from a position of strength to move the loser of the starting battle on.

The situation I laid out in the days after the Pickett trade was Cousins and a rookie quarterback drafted on day one or two, then at the end of the offseason moving Pickett on if the rookie had earned the backup role.

The Second Pickett Trade – Raiders

Before the draft, the team set up a quarterback competition of Flacco verses Pickett for the starting job. Had Pickett remained healthy then it could have been a different outcome. After the draft, sportsbooks offered odds of Flacco being the starter at +900. This was something I took full advantage of. Within twelve hours of the line being out it was -120 for Flacco with Pickett close behind. While the rookies were on the roster it was never very realistic.

If the Browns would have drafted only one quarterback then the most likely outcome would have been the loser of the head to head remaining as the backup. When they added two it always seemed like the most likely outcome.

With Gabriel playing well, the team would much rather turn to him if Flacco is benched or injured. He has a chance to be the long term answer in Cleveland, even if it is just a small chance at this stage. The odds of Pickett having a Sam Darnold level breakout are incredibly low.

Before this offseason a team had never traded for a quarterback and traded him away in the offseason. But in a modern NFL teams are more aggressive and now seen two teams do it.

Pickett held his value and cost the team nothing more than a practice squad quarterback to give them options at the quarterback position during the preseason, a very smart move by this front office.