Daniel Snyder bought the Washington Redskins in May of 1999 after the death of previous owner Jack Kent Cooke, transforming the one-proud franchise into one of the worst in the NFL. Snyder is in his 21st season owning the Redskins, a franchise that has just five winning seasons and two playoff victories in that span. The Redskins have had 11 losing seasons since Snyder took over and have never reached a conference championship game. It's added to the futility that has plagued the Redskins since winning the Super Bowl at the conclusion of the 1991 season. 

Snyder's mismanagement of the franchise is well known, and the head coaches who've been hired under his watch have been a disaster, even for Washington. No full-time head coach hired under Snyder has ever had a winning record. 

So, which head coach has been Snyder's best hire? Sorting through this list is like picking the ripest of the rotten tomatoes: 

6. Steve Spurrier (2002-2003)

This is clearly the worst hire the Redskins ever made in the Snyder era. Washington believed it was revolutionizing the NFL with Spurrier and his "fun and gun" offense. The Redskins signed Spurrier to a five-year, $25 million deal, which at the time was the richest contract given to a head coach in NFL history. Spurrier brought in several of his stars from the University of Florida that led him to prominence there, notably quarterbacks Danny Wuerffel and Shane Matthews, while Snyder pushed for Spurrier to draft Patrick Ramsey in the first round of the 2002 draft. Spurrier went 4-1 in the 2002 preseason and started the year with a blowout win over the Cardinals before the Redskins limped to a 7-9 record with the 25th-ranked offense. Washington started 3-1 the following season before losing 10 of their final 12 games and Spurrier resigned at the end of the year, forfeiting the final three years of his deal. The Redskins were 12-20 in two years under Spurrier. 

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5. Mike Shanahan (2010-2013)

The Redskins thought they were getting a home-run hire with Shanahan, but struck out swinging. Shanahan was named Vice President of Football Operations with the final say in football decisions after signing a five-year, $35 million deal. Shanahan compiled an 11-21 record after two seasons and finishing last in the NFC East both times. Washington traded three first-round picks to move up in the 2012 draft to select Robert Griffin II, but Shanahan mismanaged him while the team was on a seven-game winning streak after a 3-6 start, brining him back into a game after a knee injury in December and in a NFC Wild Card playoff loss to the Seahawks, which resulted in Griffin tearing his ACL, LCL and meniscus. Griffin already had a LCL sprain and was wearing the knee brace in a game the Redskins were up 14-0. The Redskins lost the playoff game and Griffin was not the same player the following year as Washington limped to a 3-13 record, last in the NFC East, which led to Shanahan's dismissal. Shanahan ended his Redskins career with a 24-40 record, one NFC East title, and three last-place finishes in four years. 

4. Jim Zorn (2008-2009)

While Spurrier was a splashy hire, this one was a head scratcher. Zorn was initially hired as the Redskins offensive coordinator in 2008, but Joe Gibbs retired so Zorn was promoted to head coach without ever having a position higher than quarterbacks coach. The Zorn experiment was a disaster as the Redskins lost six of eight games in his first season after a 6-2 start to finish last in the NFC East. Washington went 4-12 in Zorn's second and final season, and the head coach was removed of his play calling duties six weeks into the year. Zorn was fired after the final game of the 2009 season, finishing with a 12-20 record and never having an offense ranked higher than 26th. 

3. Marty Schottenheimer (2001)

Schottenheimer was the head coach of the Redskins for one season, due to Snyder's bad judgment. The Redskins started 0-5, but became the first team in NFL history to win five straight games after an 0-5 start. Washington won eight of its final 11 games to finish 8-8, overachieving with the 28th-ranked offense. That wasn't enough to save Schottenheimer's job as Snyder abruptly fired him to make room for Spurrier. Schottenheimer refused to relinquish his authority in making personnel decisions in case the Redskins hired a general manager, one year after hiring him as Director of Football Operations. Schottenheimer alienated veteran players with his tough practices and coaching hires, which included his son Brian Schottenheimer as quarterbacks coach. 

2. Jay Gruden (2014-2019)

Gruden being one of the most successful head coaches in the Snyder era despite not winning a playoff game is an indictment of how bad the Redskins have been. Gruden had two winning seasons as Washington's head coach, giving the Redskins back-to-back winning seasons for the first time since the 1996 and 1997 seasons. Gruden led the Redskins to first place in the NFC East two years after the Shanahan disaster with Kirk Cousins as his quarterback, falling in the NFC wild-card game. The Redskins started 6-3 under Gruden and were leading the division in 2018 when Alex Smith broke his leg and ended his season, resulting in Washington limping to a 7-9 finish. Gruden ended his Redskins tenure with a 35-49-1 record, going 1-11 in his final 12 games. Gruden is partly responsible for the emergence of Los Angeles Rams head coach Sean McVay, who served as his offensive coordinator for three years before revolutionizing the league with the Rams. Gruden knew how to assemble a coaching staff, but injuries plagued his tenure with the Redskins. 

1. Joe Gibbs (2004-2007)

Snyder's best hire was bringing back the most successful head coach in Redskins history, 12 years after he retired. Gibbs didn't come close to the level he achieved during his first stint in Washington, winning three Super Bowls, winning the  NFC East five times and having eight 10-win seasons from 1981 to 1992. Gibbs went 30-34 in four seasons with the Redskins, leading the team to two playoff appearances in three years (2005, 2007). The Redskins won their lone playoff game this century under Gibbs, a NFC wild-card win over the Tampa Bay Buccaneers in 2005. Gibbs retired after taking the Redskins to the playoffs in 2007, staying on as a senior adviser to Snyder. While Gibbs didn't have the same success as he did the first time coaching the Redskins, the franchise at least had some stability under him. Washington has only made the playoffs twice since Gibbs retired.