I always think to myself how things might have been different had Jimmy been cajoled into staying, how that team might have fared from 1996-2000 had we acquired guys like Sam Madison (44th in 1997), Patrick Surtain (44th in 1998), Jason Taylor (73rd in 1997) and Zach Thomas (156th in 1996) on our defense, as Jimmy kinda "found," all those guys after the first round for Miami. Yeah, Jimmy struggled to find another WR so you have to think the team might have struggled on offense finding a replacement for Irvin, but maybe in that case they land Randy Moss, too.
Think about the following scenario: Jerry throws every last asset and every kow-towing trick in the book at Jimmy to get him to stay after 1993, signing him to a new long term (5 year) contract.
The Cowboys are prepared for the 1994 NFCC and win in, and destroy the Chargers. The Cowboys also win yet again in 1995 though the team is still running on fumes by that point as free agency defections were unpreventable (Harper, Stepnoski, James Washington, Thomas Everett, Russell Maryland, Robert Jones all still depart by the 1994 or 1995 offseasons). They go down in history not just as the unquestioned team of the 90s, but every bit as on-par with the 80's 49ers and 70's Steelers, having won four Super Bowls not just in a decade but in a row.
In 1996 the team has a 10-6 like down year and following the season, Jimmy realizes they have to re-tool. He trades Deion Sanders to the Denver Broncos, who just finished 13-3 themselves and are trying to get over the hump, for 1997 and 1998 first round picks. In the 1997 draft the Cowboys take LB Jamie Sharper at 22 with their own pick, and with Denver's pick (28) they select Sam Madison.
* Side note, they don't need to select LaFleur at 22 in 1997, because in the 1995 draft, they select Ken Dilger at 46 instead of Sherman Williams, and between their picks at 59 and 63 with which in real life they took Shane Hannah and Kendell Watkins, they manage to stumble into Emmitt Smith clone Curtis Martin, who Jimmy recognizes as another too-small, too-slow but productive NFL runner.
In 1997 the team does not bottom out at 6-10. It is mid-retool, including still needing to re-stock the DL with the departure of Haley and the aging of guys like Tolbert and Leon Lett, and the OL is getting older as well. It does, however, have rookie Jason Taylor that it selected in the second round instead of Dexter Coakley, who it didn't' need because it had Jamie Sharper at OLB already, not to mention Zach Thomas who it found in the the third round in 1996 instead of Mike Ulafale.
Heading into the 1998 draft, the Cowboys have their own pick somewhere in the late teens, and also Denver's pick at 30 as they won the 1997 Super Bowl with Deion Sanders on the team.
With Jimmy there to guide the ship, Dallas feels empowered to select Randy Moss at 18 at history is re-written. With Denver's pick, who in real life selected WR Marcus Nash, Dallas doesn't need WR and goes with Patrick Surtain. With Dallas's own second they still manage to snag the falling, deaf-in-one-ear Flozell Adams.
The 1998 Dallas Cowboys have just come off two mediocre seasons in 1996 and 1997, but are now loaded with the following core -
Skill positions:
QB 32 year old Troy Aikman
RB1 29 year old Emmitt Smith
RB2 26 year old Curtis Martin, who has dazzled as Smith's backup but has one year remaining on his rookie contract
TE 27 year old Ken Dilger
WR1 32 year old Michael Irvin
WR2 21 year old Randy Moss
WR3 25 year old Patrick Jeffers who the team can re-sign as it's third WR since it has a little cap space with Deion's departure
OL (has solid bookend tackles but needs to continue to work on interior OL, but I bet they never end up with Clay Shiver either):
27 year old Larry Allen
23 year old Flozell Adams
Defense:
RE 24 year old Jason Taylor
LE journeyman DE FA signing (or perhaps someone like Phillip Daniels or Jevon Langford, taken in the fourth round after in real life Dallas blew a pick on Stepfret Williams in the late third).
DT 30 year old Leon Lett
DT 33 year old Chad Hennings
OLB 24 year old Jamie Sharper
MLB 25 year old Zach Thomas
OLB 25 year old Randall Godfrey
CB 24 year old Sam Madison
CB 22 year old Patrick Surtain
SS 29 year old Darren Woodson
FS 28 Brock Marion, who re-signs with Dallas instead of being lured to Miami to play for Johnson, and whose contract can be afforded with the jettisoning of Sanders and Kevin Smith, who Jimmy notices quickly declining and cuts for too many penalties.
This team gears up for another run of defensive dominance. With Aikman having three quality targets to throw to in 1998 instead of zero by the end of that season in real life, the Cowboys go 13-3 and beat Deion Sanders, John Elway and the Broncos in the Super Bowl.
And with Randy Moss absolutely taking over the league and Troy Aikman not taking a pounding due to his plethora of targets, no end is in sight.