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Five best NFL Draft night trades of all-time

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As the 2021 NFL Draft approaches, with speculation all over, everyone tries to predict what is going to happen. The most unpredictable and exciting picks sometimes come after teams trade up. This can result in some of the biggest NFL Draft trades.

Biggest NFL Draft night trades ranked

Whether a player slides or it’s just a case of a team paying up to get their guy, it’s always exciting when the move gets made. Here are the five biggest NFL Draft night trades in history.

5. Buccaneers trade back and then trade up, landing Warren Sapp and Derrick Brooks – 1995

Tampa Bay Buccaneers send the 7th overall pick and a 3rd rounder to the Philadelphia Eagles. They send the 12th overall pick and two 2nd round picks. Tampa then used one of the 2nd rounders and their own 2nd to trade back up to the 28th overall pick.

We’re starting off this list with one of the best first rounds we’ve ever seen. The Tampa Bay Buccaneers started the 1995 draft with the 7th pick of the draft but ended up trading down to 12. They used the 12th to select Warren Sapp, a defensive tackle out of Miami – who is now in the Hall of Fame. Sapp is a 7-time Pro Bowler and won the NFL Defensive POTY in 1999.

Then, with some of the equity they got from trading back, they came back into the first at 28 and drafted linebacker Derrick Brooks.

Yes, that is two HOF defensive players in the first round in the same draft. Brooks was a superstar at college in Florida State and continued in the NFL. He went to 11 Pro Bowls and he also won an NFL Defensive Player of the Year in 2002.


Derrick Brooks is one of the best linebackers in NFL history and the Bucs got him after some phenomenal manoeuvring. With Sapp and Brooks in the forefront, Tampa Bay built one of the more infamous defenses ever and they won the Super Bowl in 2003 on the back of that defense. This is one of the best first rounds of all time and these two moves, one down and one up are two [or for the purpose of this list, one] of the best NFL Draft night trades ever made.

4. Chargers and Giants draft and then swap QB’s – 2004

Los Angeles Chargers send Eli Manning (taken first overall) to the New York Giants. They send Philip Rivers (taken 4th overall), a 3rd round pick in 2004 and their 1st rounder in 2005.

If this list was centred on being infamous, or unique, we have a winner, here. The craziest and most memorable mid-draft exchange I’ve seen happened in 2004, between the San Diego Chargers and the New York Giants. With the first overall pick in the draft, the Chargers drafted Eli Manning, a player who refused to play for them. It’s a bold strategy… Well, it worked out.

While this is one of the most awkward moments you will see, and it seems funny without properly looking into it, it worked out pretty damn well for San Diego. Just three picks later, the Giants drafted QB Philip Rivers from NC State. The reason for this is because the Giants wanted Manning and the Chargers’ second-choice was Rivers. So – in real-time – the Chargers drafted Manning, then waited three picks, and traded him to New York. And, somehow, they actually got a really good deal from it.

The Chargers sent Eli Manning and received Philip Rivers, a 3rd round pick that year and two picks the next year including a 1st rounder! While drafting someone that won’t play for you is a risky choice, they got a legitimately good return. The picks they received turned into Nate Kaeding and Shawne Merriman (the 2004 4th and 2005 1st respectively). Both Kaeding and Merriman ended up heading to multiple Pro Bowls. This trade gets remembered because it was high profile, unusual and funny, but if you look at how it worked out for both teams – the Giants won two Super Bowls and the Chargers actually got three good players – it’s legitimately one of the best NFL draft trades ever made.

3. Chiefs trade up for Patrick Mahomes – 2017

Kansas City Chiefs send the 27th overall pick, a 3rd in 2017 and their 2018 1st to the Buffalo Bills. They send the 10th overall pick.

These last three trades are all straight up historic moves for the franchises that made them. We’re talking about teams who made a move and the entire future of the NFL and their organisation shifted. First, we’re going to talk about by far the best trade up in the 21st century – that, of course, is the one where Kansas City acquired Patrick Mahomes. The Chiefs had a good offense, led by Alex Smith, but they wanted more.

They traded up from 27 to the 10th pick and took Mahomes, after the Chicago Bears had already traded up and drafted Mitch Trubisky at 2nd overall.

They drafted one of the most talented quarterbacks we have ever seen [and Buffalo got Tre’Davious White, so don’t worry about them, either] and set their franchise up for the next decade. The rookie out of Texas Tech sat behind Smith for just one year and then in his first year as a starter he set the league on fire. Mahomes won the MVP in 2018 and made it to the AFC Championship Game. The next year, Mahomes continued on his unbelievable trajectory and led the Chiefs to a Super Bowl win in SB LIV. In 2020, KC returned to the biggest stage once again and lost to Tom Brady and the Buccaneers.

I will be perfectly honest; I think that this entry could very easily move up this list soon.

If Mahomes continues at the level we’ve seen so far, he will be one of the best players ever. To move further up he will need to lock in his gold jacket and win a couple more Super Bowls, but he still goes down as one of the three best draft night picks ever.

2. Cowboys trade up to get Emmitt Smith – 1990

Dallas Cowboys send the 21st overall pick and a 3rd rounder to the Pittsburgh Steelers. They send the 17th overall pick.

Like I said, to be at the very top of this list, you have to be a franchise-shifting player. How else would you describe Emmitt Smith? One of the best running backs to ever play in the NFL, Smith was the target of a trade up in the 1990 NFL draft. The Florida halfback was available at 17th overall and the Dallas Cowboys didn’t want to miss out. They jumped up four picks and secured him, by throwing in a third-round pick.

In Smith, they completed their unbelievable offense – they drafted Michael Irvin in 1988 at WR, Troy Aikman in 1989 to play QB and then Emmitt Smith in 1990 to be their running back. This three-year masterclass of drafting coincided with Jerry Jones becoming the owner and GM of the team after the 1988 season. Honestly, his first two years might have been his best ever, putting together this trio. Smith was part of one of the most dominant teams of all time. The Cowboys won the Super Bowl three times, after the 1992, 1993 and 1995 seasons. Three championships in 5 seasons.

The superstar running back won Super Bowl MVP in the second of the three and was voted to 8 Pro Bowls. Smith won the NFL MVP award in 1993, just his third year in the league. No football player has ever rushed for more yards than Smith (18,355) and I think it will be extremely unlikely that this record is broken anytime soon, if ever.

Dallas drafted unbelievably well in the three-year period at the turn of the decade, but their effort to move up and take Emmitt Smith might have been their best move in that golden era.

1. Niners trade up for Jerry Rice – 1985

San Francisco 49ers send the 28th pick, their 2nd and 3rd round picks to the New England Patriots. They send the 16th overall pick and their 3rd round pick.

The cream of the crop. If I’m going to suggest a draft pick was better than taking Emmitt Smith, it has to be pretty good. Well, how about trading up for the best wide receiver in history?

That’s who the San Francisco 49ers got when they traded up from 28 to the 16th pick in 1985. They sent a 2nd rounder and swapped third-round picks and in return they got Jerry Rice. That’s not just the best draft night trade ever, either. This is legitimately one of the best and most impactful moves in the league’s history.

Jerry Rice is a San Francisco legend, who dominated alongside two NFL greats, Joe Montana and Steve Young. Rice’s accolades are ridiculous, but none more impressive than three Super Bowl rings and a Super Bowl MVP. He is one of the true legends of postseason football and dominated in all three championship games. The Hall of Famer played for an unbelievable 20 years and retired at 42 as the best wide receiver to ever do it.

He is the all-time leader in receptions with 1,549 and both receiving yards and touchdowns with 22,895 and 197 respectively. He also has the most all-purpose yards, too with 23,540 – which is about 2,000 more than Emmitt Smith in second.

In my personal opinion, Jerry Rice is the best player to ever play a position other than quarterback. He’s one of the greatest ever, and all the Niners paid was a second-rounder and a pick swap. That deal, for my money, is the best NFL draft night trade ever completed.

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