Being a successful sportsman as well as an equally successful high-profile entrepreneur in one lifetime is a most unusual phenomenon. Some may dare suggest that the two things are incompatible.

Well, here is a man who was born in Kingston, Jamaica, and did his early schooling at St Theresa’s Prep in Vineyard Town — a school with no structured sports programme. However, as a resident of Mona Heights, he spent a lot of his early years at Buttercup Park playing football and says that he attended cricket at Sabina Park with his dad.

He recalls his first Test match back in 1968 between England and the West Indies, which he described as the match with the riot and tear gas.

Interestingly, he would have been present to see one of the best demonstrations of batsmanship by the great all-rounder Sir Garfield Sobers on a Sabina pitch that developed huge cracks which made batting for the average batsman a treacherous exercise.

From prep school he moved on to Campion College where he represented the school in every age group of football.

Chris Dehring was a member of Campion’s first team in the Manning Cup competition at the tender age of 15 years. In his second year in the Manning Cup he scored four goals, one being a free kick from 25 yards out.

To justify his father’s investment in developing his interest in cricket, he represented his school in the Sunlight Cup competition in 1978 and ’79, finishing second in the overall bowling averages in 1979.

Not to be outdone, young Dehring represented Campion at Champs running the 200 metres.

At the higher level, Dehring represented the Jamaican Under-20 juveniles at the Caribbean Football Union Championships, and the FIFA Youth World Cup qualifiers during the years 1979 to 1981.

He also played youth cricket representing the Jamaica Under-19 team along with the likes of Courtney Walsh, Patrick Patterson, and Robert Haynes. He won the award for best fielder in the regional competition.

Moving to the tertiary level, Dehring represented the UWI in 1980 and was selected to represent the All-Collegiate Team against an All Schools XI. The following year he took up a football scholarship at West Virginia Weslyan College. They won the NAIA National Championships in 1984. Dehring scored 32 goals in a four-year career and was selected to the Academic All-American Team in 1982 and the All-Conference Team in 1981.

In 1982-83, Dehring represented his university’s track and field team.

Outside of school, the all-round sportsman represented his club Real Mona in the Major League from 1978 to 1995.

He also played Senior Cup cricket for Kingston Cricket Club from 1981-1992.

Christopher Dehring continues to be active as he has been a regular participant in the Masters League for Real Mona from 1997 to the present

He is also a competent golfer having won two amateur tournaments and has attained a handicap as low as eight.

Dehring’s sporting prowess moved him to the boardroom when he was seconded to set up commercial operations of the West Indies Cricket Board (WICB) in 1997 as chief marketing executive. He negotiated a multimillion-dollar broadcast and other commercial rights deals for the WICB during his tenure as well as authored and presented the region’s World Cup bid to the ICC on behalf of Caribbean governments and the WICB.

This led to the Caribbean’s hosting of the ICC Cricket World Cup 2007 with Dehring as managing director & chief executive officer.

“Cricket World Cup 2007 turned out to be most profitable World Cup to that point, breaking records for ticket sales, TV rights, licensing and merchandising and tour and hospitality,” said Dehring proudly.

This appreciation of sports as a business inspired Dehring to create both the Red Stripe Mound at Sabina Park, the world’s first all-inclusive party stand and Sportsmax, the Caribbean’s first “24/7” sports channel, which was later sold to telecommunication firm Digicel.

So having achieved so much it is natural to assume that this “dude” is ready to “ride off into the sunset” like the proverbial old cowboy who has come to the end of an adventure.

Not Chris Dehring.

He is now CEO for the newly formed ReadyTV, while still playing Master’s League football (Over 35) as well as Golden League football (Over 45) and holds the distinction of being the second leading scorer in this year’s tournament with nine goals behind Walter Boyd (10).

I asked Chris about his proudest moment so far in life and he quickly responded: “Playing both football and cricket at the youth level for Jamaica — a rare achievement.”

For his biggest disappointments he mentions missing out on the FIFA Under-20 World Cup in 1979 staged in Japan and not playing for Jamaica’s senior men’s football team.

“I was called up once to the senior squad for a World Cup qualifier in around 1984, but was unable to make it while attending college overseas,” Dehring noted.

With his varied interests, he still has time for family as he is happily married to Katia, a native of Brasil. He has three children: step-daughter Effie (27 years) son Zachary (24), daughter Shiloh (six).

Like the typical top sportsman, Christopher Dehring likes to win. It is said that if every human being put all their best efforts into whatever they do, we would have many more “victors” than “victims”.

Christopher Dehring clearly has focused on the goal in all his endeavours and the results are there for all to see.

Editor’s note: Robbie Robinson is an attorney-at-law, public speaker, sports journalist, sports enthusiast and singer.