The New Orleans Saints didn't know it would work out this way: In 2001, the San Diego Chargers selected Drew Brees with the 32nd pick in the NFL Draft. Brees became the second quarterback taken, following the first overall pick in the draft, Michael Vick. Brees joined San Diego’s first round pick, LaDainian Tomlinson, on the pathway to eventual stardom.

As a rookie, Drew Brees only made one appearance and never started. The aging Doug Flutie held the starting quarterback job in 2001, before relinquishing it to Brees in 2002.

Drew Brees led San Diego to an 8-8 record in 2002, but he struggled in 2003. Head coach Marty Schottenheimer removed the second-year quarterback in Week 9 and reinstated Flutie as the team’s starter. After five games on the bench, Brees returned to the starting lineup in Week 15.

Through those first two seasons as a starter, Brees went 10-17, completed fewer than 60% of his pass attempts, and threw more interceptions (31) than touchdowns (28). However, the Purdue product showcased his potential the following season.

Fortunately for Brees, in 2004 the Chargers drafted Eli Manning, who they subsequently traded for Philip Rivers. San Diego’s lack of faith in Brees stemmed from his below-average first three seasons of play. No matter how well he did moving forward, it became clear that Rivers could eventually take over.

In an interview with Sports Illustrated’s Albert Breer, Brian Schottenheimer (San Diego's former quarterbacks coach) recapped a conversation he had with Brees before the draft,

“I said, ‘Hey, bro, listen, you need to prepare yourself, we’re probably taking a quarterback.’…And he looked at me and said, ‘That would be the worst f—ing mistake this organization could ever make.’ And I’m like, ‘Hey, man, don’t shoot the messenger.’ He goes, ‘Worst mistake ever.’ And he walked off.”

Brees made his first Pro Bowl in 2004, leading the Chargers to an 11-5 record. (The Saints weren't yet in the picture.) He completed 65.5% of his pass attempts and threw 27 touchdowns to only seven interceptions. Brees won Comeback Player of the Year and led the Chargers to their first playoff appearance in nine years. San Diego lost in the Wild Card Round to Chad Pennington’s New York Jets.

Following the 2004 season, Brees became a free agent. However, the Chargers tagged him as a non-exclusive franchise player. The team brought him back for one more season, but no long-term deal was forthcoming, setting the stage for his eventual journey to the Saints.

Brees started all 16 games for the Chargers in 2005, but he suffered a torn labrum in the final game of the season. He faced four months of anticipated rehab.

An article for ESPN at the time quotes Brees saying, “Who knows what’s going to happen? And I don’t. I just worry about the things I can control, and right now it’s taking care of this thing [the injury]. But I truly believe I’m going to get better and better every year.”

Despite the injury and his regressing play, the Chargers offered Brees a five-year, $50 million contract that offseason. However, Brees would only make two million dollars during the first year of the deal. The Miami Dolphins also expressed interest in Brees but stayed away because of the shoulder injury. Instead, the Dolphins started Daunte Culpepper and Joey Harrington in 2006. The rest is history for the Saints.

Ultimately, Brees signed a six-year, $60 million deal with the New Orleans Saints. That season, Brees led the NFL in passing yards and earned his only career First Team All-Pro selection.

In his fourth year with the Saints, Brees led New Orleans to the franchise’s first Super Bowl victory and won the game’s MVP award. The Chargers still do not have a Super Bowl and will search for a new franchise quarterback this offseason.

Brees recently announced in an Instagram post that he plans on returning for the 2020 season. The pending free agent will presumably negotiate a new deal with the Saints and join the team for his 20th NFL season. Brees currently holds the NFL career records for pass completions, passing yards, passing touchdowns, and completion percentage… as a member of the Saints.