JACKSONVILLE, Fla. – Shad Khan is approaching a milestone that, quite frankly, is a little embarrassing.

Khan is sitting on 99 losses as the Jacksonville Jaguars owner, and if the 1-8 Jaguars lose to the 9-0 Pittsburgh Steelers on Sunday at TIAA Bank Field, he’ll be tied for a dubious record -- the second-fastest in NFL history to reach 100 losses as an owner.

Khan will join former New Orleans Saints owner John Mecom in reaching that milestone in 141 games, including playoffs. The only owner to reach 100 losses quicker is former Tampa Bay Buccaneers owner Hugh Culverhouse, whose hapless Bucs needed just 140 games to hit triple-digit losses.

Tampa Bay lost its first 26 games -- going 0-14 in its inaugural season in 1976 -- and Culverhouse hit the 100-loss mark with a 22-20 road loss to the New York Giants on Nov. 3, 1985. That was the Bucs’ ninth consecutive loss that season. They finished 2-14.

The Bucs at least had three winning seasons and made three playoff appearances before they reached triple-digit losses. The Jaguars have had one winning season and one playoff appearance under Khan.

That’s right: The Jaguars in Khan’s nine seasons as owner are just barely better than the NFL benchmark for awfulness.

Fittingly, loss No. 100 could come against the Pittsburgh Steelers, the franchise that has been, aside from maybe the New England Patriots, the NFL’s model franchise when it comes to stability, consistency and success.

That began early in the tenure of Hall of Fame coach Chuck Noll, who was hired in 1969 and won four Super Bowls and 217 games (including playoffs) in 23 seasons leading the Steelers.

Noll had three losing seasons from 1969-71 -- which capped eight in a row for the franchise -- but since then the Steelers have had just seven losing seasons. And even those weren’t debacles: Only once have the Steelers won fewer than six games in the last 51 seasons.

Only twice -- in 1985-86 and 1998-99 -- have they posted back-to-back losing seasons. Their last losing season was 2003, which was the year before they drafted Ben Roethlisberger, and their victory over Cincinnati last Sunday clinched the franchise’s 17th consecutive non-losing season.

“I have a great deal of respect [for the Steelers organization],” Jaguars head coach Doug Marrone said. “But for me, from a playing standpoint, from people that I know that coached there, from players that have played there, I just think it’s one of the things, they’ve done a hell of a job and they’ve been a good football team. You can talk about decades. There’ll be times where they might be a little bit down, but not many.”

The Jaguars, however, have had 15 losing seasons since the team debuted in 1995 and that will increase to 16 with the next loss in 2020. They’ve had 10 losing seasons since making the playoffs in 2007 (which will become 11 with another loss), including six in a row from 2011-16.

And those losing seasons were debacles: They’ve won fewer than six games eight times since 2007 and are rapidly heading toward a ninth.

Since Khan purchased the team in November 2011 and took over before the 2012 season, the Jaguars have won just 41 games and have had just one season with a winning record. That was certainly a special season -- a 10-6 finish for the franchise’s first division title since 1999 and two playoff victories before losing in the AFC Championship Game -- but it doesn’t make up for the fact that the Jaguars have won fewer than six games six times (and No. 7 is on the horizon) in Khan’s nine seasons.

The things that have made the Steelers so good are the same things that have made the Jaguars not good. Pittsburgh has had three head coaches since 1969 (Noll, Class of 2020 Hall of Famer Bill Cowher and Mike Tomlin), hit on the most important position (quarterback) and drafted and developed exceptional talent. Since 1996, for example, the Steelers have drafted 23 players who made at least one Pro Bowl, per Elias.

Meanwhile, in the same time span, the Jaguars have six head coaches (five if you don’t include Mel Tucker, who was the interim head coach for the final five games of 2011), have missed on first-round quarterbacks three times in their quest to replace Mark Brunell and have drafted 16 players who went on to become Pro Bowl players.

The Steelers were the measuring stick for the Jaguars in the early years of the franchise when they both played in the AFC Central. The Jaguars won the first game in the series, which was also the first home victory in franchise history, and the Jaguars at one point won three in a row and five of six in the series.

The Jaguars also are the only team to beat the Steelers in Pittsburgh twice in the same season. They did it in 2007 and 2017, upsetting the Steelers in playoff games.

None of that matters on Sunday because the Steelers are the league’s best team and a 10-point favorite, which makes it likely that Khan will pick up his 100th loss -- and with it, an embarrassing piece of NFL history.