He worked for the Heartland Wrestling Association[6][7] twice winning the HWA Tag Team Championship with Cody Hawk as part of The Surf 'N' Turf Connection.
[2][11] His long-running rivalry with IWA Mid-South Heavyweight Champion Bull Pain was a prominent storyline in the promotion's history as well as one of the biggest feuds on the Midwestern independent circuit.
From 1998 to 2001, Keen was part of The Old School Posse with GQ Masters III, Sean Casey, Shark Boy, and manager Dutch Mantell which antagonized the promotion's hardcore wrestlers for several years.
In November 1997, he began wrestling under the name "Chip Fairway", an ex-golfer turned pro wrestler, and remained undefeated during his first five months in the promotion.
[17][18] Fairplay failed to regain the title from Pain at IWA Mid-South's Eddie Gilbert Memorial Show[13][19][20] but won it back in Louisville on March 12.
On April 29, Fairway and Shark Boy defeated Terek the Great and "Live Wire" Sean Casey at the 1st Annual Brian Pillman Memorial Show.
[37] The Surf 'N' Turf Connection held on to the belts for six months before dropping them to Alexis Machine and "Beautiful" Brian Fury in Blanchester on August 25, 1999.
[12][40] Also that summer, Fairway was among the cruiserweight wrestlers invited to take part in a special championship tournament held at the Cincinnati Gardens for the 2nd Annual Pillman Memorial Show.
[12] On January 3, 1999, Fairway wrestled Mitch Page and Twiggy Rameriz in a 3-Way Dance at Barbwire, Bulbs, and Blood in Charlestown, Indiana.
A month later, The Surf 'N' Turf Connection lost to Alexis Machine and Brian Fury in a match for the HWA Tag Team Championship.
On the night of the semi-finals, he attempted to interfere in Shark Boy's title defense against Matt Stryker and Astin Agustus Ambrose but was prevented by the latter.
He and Shark Boy (with Nick Roll) wrestled to a double-disqualification the following night in Lebanon, Ohio when Brian Fury, Bobby Casanova, Anthony MacMurphy and Cody Hawk all ran in.
[52] Fairway lost the bout when his manager, local disc jockey Mark Amazon, attempted to hit Steele with a golf club.
The final fall was awarded via disqualification when Ambrose was lured away from the ring by Bennie the Bookie allowing Tim Moxley to attack Shark Boy from behind.
HWA Commissioner Patrick Black was forced to declare a no contest and ordered a ladder match to take place when the promotion returned to Hamilton.
[49] As a result of the 6-way brawl in Lebanon two months earlier, HWA Commissioner Patrick Black ordered a six-man tag team elimination match with the added stipulation that Nick Roll and G.Q.
The bout was held when the promotion returned to Lebanon on July 28 which pitted Fairway, Brian Fury and Bobby Casanova against Shark Boy, Cody Hawk and Anthony McMurphy.
On August 26, Fairway urged Fox to attack Future Shock during their six-man tag team match against The GQ Corporation (Bobby Casanova, Brian Fury and Alexis Machine).
Fox knocked out both Whitmer and Caine with a steel chair, allowing Alexis Machine to eliminate both men, before leaving with Fairway.
Fairway whipped Steele into both the ladder and referee Joe Kopasz giving Fox a chance to climb to the top and retrieve the HWA Heavyweight Championship.
At the two-day Classicfest in Fort Loramie, Ohio, Fairway defeated Logan Caine by submission to win a title shot against Race Steele.
By this time, Fox had developed a prima donna personality and lashed out at Future Force and the fans for not giving him the respect he deserved as an "MTV superstar".
[49] On September 23, Fairway (with Rory Fox) wrestled Matt Stryker (with Hellena Heavenly) at Cincinnati's Western Sports Mall.
Angry that Fox had cost him the match, Fairway slapped his caddy across the face and demanded that he make up for the loss by winning the 4-Way Dance in the main event.
Fox managed to outlast Chad Collyer and Tim Moxley but was unable to win the Cruiserweight title from Shark Boy.
Two weeks later, Fairway and Chad Collyer (with Hellena Heavenly) lost to Shark Boy and HWA Heavyweight Champion Race Steele.
He later distracted the referee so that Shark Boy could hit Page with a missile dropkick from behind and allow Masters to score a pinfall over his fallen opponent.
With Dean Baldwin as special guest referee, he defeated B. J. Whitmer in the opening round but was eliminated by Harry Palmer in the quarterfinals the following night.
The following week, Fairway returned to the House of Hardcore where wrestled Trent Baker and Hido in a 3-Way Dance for the IWA Mid-South Heavyweight Championship.
[4][6][7][10] Several wrestlers were present at his memorial service including Cody Hawk, Sean Casey, Shark Boy, The Suicide Kid, Astin Augustus Ambrose, and HWA senior referee Joe Kopasz.