Fortune favors the bold. Or so they say.
One thing you can say with certainty about New England Patriots coach Bill Belichick during his tenure in New England is that he’s been bold. From on-field decisions that have worked out (safety in Denver, no timeout in Super Bowl 49) to those that haven’t (fourth-and-2 in Indy, benching Malcolm Butler in Super Bowl 52), Belichick has never been afraid to make a risky call when the chips are down and stakes are high.
The same applies to his work in the front office. Many of the in-season and draft-day deals he’s made have worked out quite nicely, most notably his 2007 wheeling and dealing for for Wes Welker (a second rounder) and Randy Moss (a fourth rounder), with a hat tip to acquiring Aqib Talib for peanuts in 2012. It should be noted that Belichick has worked with a number of GMs and executives in orchestrating his biggest deals over time, like Scott Pioli, who was with the team for the better part of Belichick's first decade in New England. We know that Belochick has had a say or hand in any move made by the team from the time he came over in a blockbuster trade himself in January of 2000.
Yet it’s the deals that haven’t worked out, the ones that left us wondering, “Wait, really?” that come to mind on the heels of dealing former Defensive Player of the Year Stephon Gilmore in-season to the Carolina Panthers for a 2023 sixth-round pick. The haul seems a paltry sum given the cornerback’s talent level and accomplishments. And if New England was intent on never re-signing him, perhaps a deal at a previous date would have netted more. That is up for debate on sports radio and in bar rooms across Pats Nation.
Also up for debate? Where the Gilmore deal ranks in terms of the worst or most head-scratching trades during the Belichick era. Time will tell, since Gilmore won’t be suiting up for the Panthers for a few weeks. Until such time here are the five trades that continue to raise brows and force the Foxboro Faithful to wonder exactly what their brilliant coach and GM was thinking.
5.) DUANE STARKS
Following a very public and acrimonious contract dispute with cornerback Ty Law, Belichick decided to let the star cornerback walk following the 2004 season, which culminated in a Super Bowl 39 victory (where Law was injured and receiver Troy Brown played corner). To replace the soon to be Hall of Famer Belichick dealt a third-rounder for Arizona corner Duane Starks, who had been a member of the Baltimore Ravens Super Bowl winning 2000 defense. Starks was torched routinely and ultimately injured his shoulder, ending what was a very forgettable and unfortunate season, and a misguided effort to replace an all-time Patriots great.
4.) DEION BRANCH
Yet another public contract dispute that lead to a questionable decision by the HC of the NEP. Branch, a two-time Super Bowl champ, Super Bowl 39 MVP and favorite target of then QB Tom Brady, was looking for a deal that would pay him like an upper-echelon receiver. Belichick, who rarely pays the freight on a big second contract, felt otherwise, and made a deal that sent Branch to Seattle for their first-round pick. The haul seems appropriate, yet it lands on this list because Brady was left with a spare parts receiving crew in 2006, with the likes of Doug Gabriel, Jabar Gaffney and Reche Caldwell as primary targets. And those targets came up short in the 2006 AFC Championship Game in Indianapolis when a key catch of two by the likes of a Branch could have sent the Patriots to Super Bowl 40 and a date with Rex Grossman’s Chicago Bears.
3.) MOHAMED SANU
Belichick said famously, post the Brady departure from New England, that the team “sold out” in the 2019 season, and that the team always made every decision that they thought would help Brady. The latter could be debated ad nauseam (see previous Branch deal), but the former holds merit. The Patriots brought Josh Gordon back after a 2018 suspension and signed receiver Antonio Brown to what came to be the most expensive 11-day contract in NFL history. Having been burned by both moves the team made a desperate reach for receiving hep with Julian Edelman injured and Matt LaCosse leading the tight end ranks, sending a second round pick to Atlanta for Sanu. Sanu had a productive debut versus the Ravens in defeat (10 catches, 81 yards, 1 TD), but following a punt return injury against the Eagles two weeks later Sanu was unable to contribute positively in any way. Couple this with Sanu’s 2020 release and San Francisco's successful acquisition of the other receiver the Patriots had been linked to, Emmanuel Sanders, and this became a regrettable waste on multiple levels.
2.) CHANDLER JONES
Perhaps the quintessential example of Belichick getting out before the big pay day, the move that sent Chandler Jones to Arizona will forever be the biggest “What If?” move of the coach/GM’s time in Foxboro. The defensive end was sent to the Cardinals for what seemed a sum less than Jones’s talent at the time, let alone what he would become -- guard Jonathan Cooper and a second-round pick. The move lent the Patriots some salary cap room down the road, which allowed for the re-signing of linebacker Dont’a Hightower and the contract of ... Gilmore. And that second-round pick as turned into a third and fourth which netted Joe Thuney and Malcolm Mitchell. Mitchell only played one season in the NFL, but was a key Super Bowl 51 contributor and Thuney was a top guard for five seasons before leaving for a massive payday in Kansas City, so it wasn’t all bad. Had Belichick foreseen what kind of player Jones would turn into then perhaps he may have asked for more. Jones has 65 sacks (and counting), over 100 QB hits and 19 forced fumbles, making him a consistent threat to quarterbacks and arguably the best pass rusher around the league every game he’s played (he did miss most of 2020 with a torn bicep). While it’s not a wash, nor a massive L for the Pats you can’t help but wonder what the defense would have looked like had the former Orangemen standout gotten that second contract in New England.
1.) JIMMY GAROPPOLO
The Jimmy Garoppolo deal, or saga really, will forever be one of the most dramatic, controversial and debated moves in Patriots history. The unique nature of the circumstances surrounding this deal may also never be replicated on any other team, ever. Garoppolo, having been drafted as the likely heir apparent to Brady, was represented by the same agent, Don Yee, as Brady, making negotiations and leverage for the coach/GM incredible difficult. Stories abound, in multiple books no less, as to whether Belichick planned to ever replace Brady permanently with Garoppolo, and when so. Logic would dictate that there was indeed a succession plan behind the scenes, hence the rumor of Belichick turning down offers for Garoppolo, including one, allegedly, from the Cleveland Browns for multiple first round picks. Eventually, well after Garoppolo filled in for Brady during the latter’s 2016 suspension, Garoppolo became expendable after Brady’s pliability-based resurgence. And thus, out of the blue, on Halloween night 2017 Belichick sent perhaps his most valuable asset ever, a starting caliber quarterback he viewed as worthy of supplanting the GOAT, to the San Francisco 49ers for but a second-round pick. Spare us the thread of what the Patriots turned that pick into eventually. Someone of Garoppolo’s value then should have landed the Patriots a haul large enough to virtually reboot the franchise, or at least enough picks to help make up for ones lost to scandal or blown on the likes of Dominique Easley and Antonio Garcia last decade. Instead, again, Pats fans are left wondering how and why someone so valuable and cherished by the organization landed them so little. Perhaps an overplay of the asset by Belichick, like Gilmore could very well be, too.