He led the Trinidad and To­ba­go Pro League through sig­nif­i­cant fi­nan­cial chal­lenges. He had the skill set, knowl­edge and vi­sion.

Some of the most for­ward-think­ing con­ver­sa­tions I have ever had about sport on the whole in Trinidad and To­ba­go and its foot­ball in par­tic­u­lar were with Dex­ter Skeene, the for­mer out­stand­ing na­tion­al play­er and T&T Pro League chief ex­ec­u­tive of­fi­cer (CEO).

The ideas that Skeene had about the busi­ness of foot­ball and sports mar­ket­ing gen­er­al­ly may have been ahead of his time.

A few days ago, I read in both the New York Times and Bloomberg News about a bil­lion-US-dol­lar in­vest­ment in a sports in­vest­ment firm. I mar­velled at the fact that es­tab­lish­ing a sports in­vest­ment firm was a con­ver­sa­tion Skeene and I had decades ago, as we both saw sports in T&T and the Caribbean as growth as­sets.

Those con­ver­sa­tions/de­bates were ro­bust, chal­leng­ing and dri­ven by big ideas sur­round­ing mar­ket­ing and the ecosys­tem re­quired to sus­tain pro­fes­sion­al foot­ball here on the twin-is­land Re­pub­lic. He was ap­point­ed CEO of the TT Pro League in April 2004; he an­nounced his res­ig­na­tion on March 2, 2018, ef­fec­tive April 1, 2018.

He rep­re­sent­ed Trinidad and To­ba­go at both ju­nior and se­nior lev­els from 1982 to 1993 on more than 30 oc­ca­sions (in­clud­ing World Cup qual­i­fiers). He al­so played for St Mary’s Col­lege. While pur­su­ing a BA de­gree in eco­nom­ics, he rep­re­sent­ed Co­lum­bia Uni­ver­si­ty (Ivy League) in Di­vi­sion 1 of the NCAA, where he was se­lect­ed as an All-Amer­i­can.

Ac­cord­ing to the New York Times, lead­ing sports in­vest­ment firm Arc­tos has been ac­quired by pri­vate eq­ui­ty gi­ant KKR, which took con­trol of Arc­tos Part­ners in a deal val­ued at $1.4 bil­lion, giv­ing the pri­vate eq­ui­ty gi­ant a sig­nif­i­cant foothold in pro­fes­sion­al sports.

Arc­tos holds an ex­ten­sive port­fo­lio of own­er­ship across every ma­jor North Amer­i­can sports league, from the NFL and NBA to MLB, and in the NHL and MLS.

In the NBA, it holds mi­nor­i­ty stakes in the Gold­en State War­riors, Philadel­phia 76ers, Utah Jazz and sev­er­al oth­ers, in­clud­ing a stake in the Wash­ing­ton Wiz­ards, which it ac­quired in De­cem­ber. It bought an 8 per cent stake in the Los An­ge­les Charg­ers last year and al­so holds shares in the Los An­ge­les Dodgers and the Chica­go Cubs. It al­so has a per­cent­age of the gi­ant foot­ball club PSG.

KKR, in a state­ment, said it will ben­e­fit from Arc­tos’ re­la­tion­ships and ex­per­tise in the sports mar­ket. At the same time, Arc­tos now has ac­cess to more po­ten­tial cap­i­tal as it joins a firm with more than $750 bil­lion un­der man­age­ment.

Arc­tos is at the fore­front of pri­vate eq­ui­ty in­vest­ment in sports. It launched in 2019, co-found­ed by Ian Charles and Doc O’Con­nor.

Arc­tos’ growth mir­rored the in­creas­ing role of pri­vate eq­ui­ty in pro sports as more firms took pas­sive mi­nor­i­ty stakes in teams, and sports them­selves be­came a boom­ing in­vest­ment sec­tor.

Ma­jor pri­vate eq­ui­ty firms have since en­tered the sports in­dus­try. The NBA ap­proved them as po­ten­tial in­vestors in 2020, al­low­ing them to own no more than 20 per cent of a team and 30 per cent in ag­gre­gate. In 2024, the NFL let them in, though capped at 10 per cent stakes—ny­times.com.

Ac­cord­ing to Bloomberg.com, KKR sees ARC­TOS as the lynch­pin of a 100 bil­lion US dol­lar busi­ness.

“If we didn’t think that was achiev­able and re­al­is­tic, this deal makes a lot less sense for us; it gives you a sense of the am­bi­tion of what we’re try­ing to build.” – KKR co-chief ex­ec­u­tive of­fi­cer Joe Bae.

As I re­flect on the ideas and plans shared and de­bat­ed with Dex­ter Skeene in the years 2004-2018 while read­ing about KKR and ARC­TOS I didn’t know whether to laugh or cry.