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Ranking the 20 best moments of Drew Brees' 20-year NFL career

Drew Brees has retired, just a few months after Philip Rivers, a quarterback with whom Brees will forever be linked in NFL lore. In January, I looked at Rivers' standing among NFL quarterbacks who never won a Super Bowl -- and thanks to Brees' departure from San Diego, he was able to dodge that list.

So now, as we bid farewell to Brees, I present the 20 best moments of Brees' 20-year NFL career.

20) Drafted by San Diego Chargers in 2001

Let me give the Chargers some credit here. This was a bold move. San Diego had the top pick in the 2001 draft, and Michael Vick was the sure-fire selection at No. 1. No doubt about it. Maybe the Bolts lucked out, motivated by a desire not to pay a huge signing bonus to Vick. But regardless, they sent that pick to Atlanta and took LaDainian Tomlinson with the Falcons' fifth overall selection. Then, they used their own pick at the top of the second round on Brees. Drafting two Hall of Famers with their first two picks -- after trading out of No. 1 overall -- is pretty damn impressive. And look, had the Chargers drafted Larry Fitzgerald first overall in 2004 and stuck with Brees instead of acquiring Rivers, we could be having a very different conversation today.

19) Week 4, 2005: San Diego Chargers 41, New England Patriots 17

Brees made a surprise return to San Diego in 2005 -- the team placed the franchise tag on him -- after most assumed he'd hit the free-agent market. The Chargers struggled out of the gate, winning one of their first three games. But then Brees helped lead the Bolts to a huge win over the Patriots, passing for 248 yards and a pair of touchdowns. Had Brees not won that game, maybe he would have been replaced as the starting quarterback. Then he might not have injured his shoulder, which ultimately played a role in leading him to another team. But we'll touch on that in a bit.

18) First (and only) appearance of his rookie campaign

Doug Flutie was the Chargers' starting quarterback when Brees was drafted. The rookie sat behind the veteran for almost all of the 2001 season, until Week 8 against the Kansas City Chiefs. Brees replaced the injured Flutie shortly before halftime, when the Bolts were trailing 16-0, and the deficit grew to 19-0 by the half. Brees rallied the Chargers for 20 unanswered points to give his team a 20-19 lead after his touchdown pass to Freddie Jones. Now, as a Chargers season-ticket holder at the time, I knew how it was going to end, and the Chiefs ended up winning, 25-20. Brees actually had a chance for one last rally that fell short, but look: He was a rookie making his first appearance. Just getting the Chargers back in that game was huge. Of course, Flutie returned the following week and held onto his spot for the rest of the year.

17) Week 14, 2006: New Orleans Saints 42, Dallas Cowboys 17

We need to remember Brees didn't come in and immediately tear it up for the Saints. Those first weeks were like the first season of Parks and Recreation -- not essential viewing. But Brees absolutely went off against the Cowboys late in the season, throwing for 384 yards and five touchdowns. This was the kickstart the Saints needed, and it eventually led them to the NFC Championship Game, where they lost to the Bears. But you could tell things were heating up.

16) 2011 NFC Wild Card Game: New Orleans Saints 45, Detroit Lions 28

The 2011 season was wild, man. The Saints finished with a 13-3 record but still ended up with the third seed in the NFC. (Yes, the 49ers and Packers had pretty good teams that season.) Although, by ending up as the No. 3 seed, the Saints got a chance to play an overmatched Lions squad in the opening round of the playoffs. Brees threw for 466 yards and three touchdowns as the Saints cruised to an easy victory.

15) Week 7, 2011: New Orleans Saints 62, Indianapolis Colts 7

Let's stick with 2011 and revisit this HUGE Sunday night performance. I mean, it did come against Dan Orlovsky and Curtis Painter, and thus did not quite have the luster that knocking off Peyton Manning would have had. But Brees threw for 325 yards and five touchdowns. That 2011 Saints team might have been the best he played on -- well, the best offense, at least. The defense wasn't great, but damn, New Orleans could score.

14) Week 4, 2003: Brees catches touchdown from LaDainian Tomlinson

You know, I've always said that Tomlinson was the closest thing to Walter Payton I've seen in my lifetime. So it makes sense that L.T. was pretty good at the halfback option himself. Tomlinson hit Brees on a 21-yard touchdown pass against the Raiders in Week 4 of the 2003 campaign. Honestly, this moment would rank a lot higher if the Chargers had actually won the game. But they lost in overtime. (This was the year after the Raiders' Super Bowl appearance, so it's not like the Raiders were bad or anything.)

13) 2006 NFC Divisional Round: Brees earns first playoff win with Saints

Brees led the Saints to the playoffs for the first time since 2000 during his first season with the club -- even earning a first-round bye -- and he got his first playoff win for his new club with a 27-24 Divisional Round victory over the Philadelphia Eagles. Brees threw for 243 yards and a touchdown. It was the start of something special for the Saints in the playoffs.

12) 2012 campaign marks seven consecutive 4,000-yard passing seasons

Brees had an interesting 2012 season. He failed to throw a touchdown against the Atlanta Falcons in Week 13, which snapped his streak of 54 consecutive games with a touchdown pass. I mean, it had to end at some point. But he surpassed 4,000 yards for the season in Week 14 against the New York Giants, giving him seven consecutive seasons with at least 4,000 passing yards and breaking Peyton Manning's record of six seasons. So he had that. His streak continued for five more seasons, until 2018, when he fell 8 yards short of accomplishing the feat in a 13th consecutive campaign.

11) Week 8, 2004: San Diego Chargers 42, Oakland Raiders 14

Brees held off Philip Rivers as the Chargers' starter in 2004 (partly because Rivers held out for most of the summer). His best game happened midway through the season, when he threw for 281 yards and five touchdowns to beat the Raiders. This was the first time Brees would be selected as his conference's Offensive Player of the Week -- an honor he earned 25 times (twice while playing in the AFC, 23 times in the NFC) in his career. It also helped lead the Chargers to the 2004 AFC West title. Brees ended up being named the NFL's Comeback Player of the Year.

10) Week 8, 2015: New Orleans Saints 52, New York Giants 49

Brees and Eli Manning combined for 13 touchdowns in this contest. Brees tied the league's single-game record with seven touchdown passes (and I had him on my fantasy team that year, so shout-out to me). Brees also topped 500 passing yards in a game for the second time in his career. This was also just the fourth time in NFL history two teams combined for more than 100 points.

9) Week 12, 2009: New Orleans Saints 38, New England Patriots 17

The Saints were 10-0 and ready to host the New England Patriots in Week 12. Some thought this could be a potential Super Bowl preview. Brees had one of the best games of his career, throwing for 371 yards and five touchdowns while notching a perfect passer rating (158.3), and the Saints smoked the Pats.

8) Week 8, 2008: Exacting SWEET revenge on the Chargers

Maybe this 37-32 result plays into my pettiness. But Brees got his first crack at the San Diego Chargers in 2008 and had one of the best games of his career up to that point, throwing for 339 yards and three touchdowns in a flawless effort. Well, there was a safety in the closing moments -- so it was near-flawless. I know sometimes we make too much of REVENGE GAMES and whatnot, but this was certainly one of those times when it lived up to the hype.

7) Brees throws for 5K for the first time in 2008

Throwing for 5,000 yards in a season is kind of a big deal. In fact, it's happened just 12 times in NFL history. Brees has done it five times. FIVE TIMES. The first time was kind of exciting. He finished just short of Dan Marino's then-long-standing record of 5,084 passing yards (Brees finished with 5,069). Brees hit the 5,000-yard mark for the final time with 5,208 yards in 2016.

6) Breaking Johnny Unitas' record for consecutive games with a TD pass

Brees has a plethora of records to his credit during his playing career. One of the most impressive, for me, happened in 2012, when he broke Johnny U's record of 48 consecutive games with a touchdown pass. (Brees' record still stands, at 54 games). Of course, he threw the clinching touchdown against the Chargers in Week 5, breaking the record of a former Charger ... wait, did Johnny U play for a team other than San Diego? That record had stood for 52 years.

5) Brees signs with the New Orleans Saints

I know a lot of you kids might not realize that back in 2006, Brees was very close to signing a free-agent deal with the Miami Dolphins and their second-year coach, Nick Saban. And who knows how the NFL might have changed if Brees had passed his physical with Miami (the Dolphins got cold feet and eventually traded for Daunte Culpepper). Maybe Saban would've enjoyed Alabama-like success with Brees in South Beach. But things worked out well for Brees and New Orleans -- and the Crimson Tide, for that matter. For the Fins? Not so much.

4) 2006 Walter Payton NFL Man of the Year

Prolific passing seasons were a hallmark of Brees' career, both in San Diego and in New Orleans. But Brees was (and still is) well known for his work in the community, too. Brees arrived in New Orleans in 2006 and led the NFL with 4,418 passing yards and also tossed 26 touchdowns. But in one of the biggest moments of his career, he was selected as a co-recipient of the Walter Payton NFL Man of Year Award -- one of the league's most prestigious honors that, in part, recognizes a player's volunteer and charity work -- with his former teammate, LaDainian Tomlinson. Brees immediately became involved in rebuilding New Orleans after Hurricane Katrina, and he also continued to serve the community of San Diego.

3) Having an MVP-worthy 2011 ...

Let's go back to that 2011 season, when Brees finally did break Marino's single-season passing yards record, shattering it, actually, with 5,476 yards. And Brees, of course, went on to earn his first-ever MVP award ... (checks notes) ... OH, WAIT! He wasn't the MVP, with the award being given to Aaron Rodgers´╗┐ instead. Yes, Brees was selected as the 2011 Offensive Player of the Year. And, I mean, that's still a cool award. But that's like winning the Intercontinental Championship and not the World Championship. I should point out Brees also led the NFL in completion percentage and passing touchdowns. His 46 TD tosses were, obviously, a Saints franchise record. And while Rodgers ended up getting two more MVPs, Brees ended up going his whole career without one.

2) Brees becomes NFL's all-time passing leader

Credit to the NFL schedule-makers, who perfectly crafted this moment for Monday Night Football in Week 5 of the 2018 season, when Brees became the most prolific passer in NFL history, breaking Peyton Manning's all-time mark. The clinching pass came on a 62-yard touchdown pass to Tre'Quan Smith, just before halftime. And it should be noted Brees nearly completed every pass in that game, going 26 for 29 (89.7 percent).

1) Saints win Super Bowl XLIV

The most obvious pick here. Not only was this one of the greatest redemption stories for an NFL player and castaway, but it was also a redemption story for the city of New Orleans after Hurricane Katrina. I don't believe it's hyperbolic to say it was one of the most important moments in NFL history. I can't think of anybody (except Colts fans) who wasn't rooting for the Saints to win this game. It wasn't his most prolific passing performance of his career; he threw for 288 yards and a pair of touchdowns. But most importantly, he was selected as the game's Most Valuable Player.

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