Sammy is the only captain to have won World T20 twice. He led West Indies to the 2012 ICC World Twenty20 win over Sri Lanka, West Indies' first major trophy in 8 years (having won the ICC Champions trophy against England in 2004). Sammy again led the West Indies to victory over England at the 2016 ICC World Twenty20. Sammy captained Peshawar Zalmi in the Pakistan Super League from 2017 to 2020 when he retired due to fitness concerns. He then agreed to a two-year head coaching contract for Peshawar Zalmi, a position he currently holds.

On 5 August 2016, Sammy was informed that he had been dropped as West Indies T20I Captain.

For his contribution to the return of international cricket to Pakistan, Sammy was awarded Pakistan's highest civilian medal, Nishan-e-Pakistan, on 23 March 2020. He was also awarded Pakistani honorary citizenship by Pakistani President Arif Alvi.

In June 2021, Sammy was appointed to the Cricket West Indies (CWI) Board of Directors as an independent non-member.

International cricket career
Early international career

When the West Indies toured India in January 2007, Sammy was included in the squad with a chance to make his Test debut. However, just before the team left, he sustained an injury that ruled him out of the tour. Following this setback, Sammy traveled to England in April and May where he played in the Central Lancashire League ahead of the West Indies tour of the country in May. He was selected to the touring squad. This time the team won the NatWest Limited Overs Series. And the 23-year-old St Lucian won his first test match in the third test match at Old Trafford on June 7. He claimed his first Test wicket when he sacked Alastair Cook, who was caught by Dwayne Bravo, but his first innings were unremarkable other than economy, giving up just 1.88 runs per over from 17 overs completed. In the second innings, however, Sammy caught England captain Michael Vaughan with his own bowling, with England scoring 99/2. In his 17th over he had caught Ramdin's Ian Bell. Next ball he had Matt Prior down the same path. A few balls later he sacked Liam Plunkett, caught by Bravo, with the same result. Five wickets gone, four to Sammy, three in five balls. He continued his excellent debut, taking wickets from Steve Harmison and Monty Panesar before snapping Paul Collingwood to finish with seven wickets for 66 carries. His bowling numbers were the best at Old Trafford since Malcolm Marshall's 7/22 in 1988 and the best of any West Indian on debut since Alf Valentine won 8/102 in 1950.

As an all-rounder, Sammy hasn't covered himself in glory on this tour, averaging just 14.20 runs from 10 innings, unbeaten twice. He had just the 10th-highest total on a tour that included matches against Scotland and the Netherlands. As a bowler, he excelled with a team-best average of 17.72, 18 wickets (third on team) from 93.5 overs (five other players bowled more overs than Sammy).

Sammy was called up to the Stanford Superstars, a team put together by American billionaire Allen Stanford when Dwayne Bravo retired with an injury. He wasn't scheduled to play the first game, but Shivnarine Chanderpaul had a neck strain that ruled him out. All Sammy did was provide electric field and consistent bowling to force his way into the side. As expected, the Superstars made it to the final of the series where they will face off against England. The prize money was $20 million, with $1 million each going to the players on the winning team. Bowling first, the Superstars sack England for 99 runs. Sammy took 2/13 and made a catch. He didn't hit in the series.

Captain of the West Indies

On 17 October 2010, Sammy was named West India Test Team captain for his tour to Sri Lanka and through the end of the 2011 season, replacing Chris Gayle. At the time, Sammy had played 8 Tests and 41 ODIs. The previous captain and runners-up, Chris Gayle and Dwayne Bravo had opted not to sign central contracts with the West Indies Cricket Board and were replaced. Between January 2004 and the start of the Sri Lanka tour in November, the West Indies had won just five of their previous 62 Tests and were expected to lose the three game series to a team with a good home record. In a streak shortened by bad weather, Sammy hit 10 runs and took two wickets for a 75.50 average, and while he said he wanted to improve his own performance, Sammy stated he was pleased with the 0-0 result of the streak . In the 2-0 loss to Sri Lanka in the ensuing ODI series, Sammy hit 28 runs and down 19 wicketless overs.

Pakistan toured the West Indies in April and May 2011 for a T20I, five ODIs and two tests. In the first game of the Test series, West Indies secured their first win since 2009, ending a 17-game winless streak. Sammy won seven wickets in the match, including five in Pakistan's second inning, and was named Man of the Match for his performance. West Indies lost the second match, drawing the series 1–1; Sammy was his team's second-highest wicket-taker, claiming ten at an average of 17.90. The following month, Sammy was named T20I Player of the Year at the West Indies Players Association Awards. As India toured in June and July, the West Indies lost the Test series 1–0. Cricinfo reported that Sammy led with passion and "shook his heart out of his sleeve"; He finished with seven wickets from three games for an average of 38.28. During the game, Sammy had to deal with distractions from hostile crowds and pundits criticizing his appointment as captain, as some believed he could not hold his own as a player.
Originally named as captain through the end of the 2011 season, Sammy was retained as captain for all formats for the Bangladesh and India tours. In October, Sammy's main Class B contract was renewed; He was one of four players with a Class B contract, the second highest category (Shivnarine Chanderpaul was the only player with a Class A contract). Later that month, the West Indies toured Bangladesh. Sammy missed the first ODI through illness but returned to captain the team in the remaining two. West Indies won the series 2-1 and Sammy took two wickets. The first test was interrupted by rain and ended in a tie, and Sammy got the highest score for his team. After playing 17 Tests, the innings of 58 runs from 43 balls was Sammy's first half century in the format. West Indies won the second Test to win the series, and in the process Sammy sacked Bangladeshi all-rounder Shakib Al Hasan to claim his 50th Test wicket.

Domestic and T20 Franchise Career

At the launch of the Caribbean Premier League, Sammy was announced as a franchise player for the 2013 tournament.

Sammy played professionally in the Indian Premier League for Hyderabad and was named captain of that franchise in 2014. For the 2015 edition, he was sacked by Hyderabad and subsequently signed by Royal Challengers Bangalore. He was then picked up by Kings XI Punjab for the 2017 tournament.

Khyber Pakhtunkhwa Chief Minister Pervaiz Khattak offered the all-rounder honorary citizenship of Pakistan in response to a special request from Peshawar Zalmi Ownership, which Sammy accepted. Sammy played for Peshawar Zalmi in the inaugural Pakistan Super League in 2016. He was retained by Peshawar Zalmi in the 2016 PSL draft. During the draft, Captain Shahid Afridi made the impressive announcement of naming Sammy as the new captain of Peshawar Zalmi. With Sammy as the popular captain, the club won the second edition of the Pakistan Super League in 2017.
In May 2018 he was named as one of the ten marquee players for the first edition of the Global T20 Canada cricket tournament. On June 3, 2018, he was selected to play in the player draft for the inaugural edition of the tournament for the Toronto Nationals. In June 2019, he was selected to play for the Brampton Wolves franchise team in the 2019 Global T20 Canada tournament. In July 2020, he was named to the St. Lucia Zouks roster for the 2020 Caribbean Premier League.

Play Style

Sammy has a reputation for bowling long spells and his medium speed bowling is used to assist strike bowlers. He has commented: "We all have roles in the team and I clearly understood what my role in the team is, which is to push and be the workhorse of the team. I accepted that and that's how I've played throughout my career ." He aims to do this by bowling point balls to create pressure. Sammy feels that batsmen relax against him and are more prone to error because he's a supporting bowler. A consistent bowler despite not moving the ball much, Sammy delivers the ball with an upright seam and uses the crease to vary his throwing angle. As a batsman, his strike rate in ODIs of 98.11 is the second-highest among West Indian players who have experienced at least 500 deliveries (behind all-rounder Andre Russell at 119.34), and he holds second in ODI innings of at least 25 runs, 3rd and 4th highest scoring rate of West Indian players.

Racism

In a series of posts on his Instagram Stories, he said some of his teammates from IPL team Sunrisers Hyderabad called him "Kalu". He also said he learned those were derogatory words after watching popular comedian and satirist Hasan Minhaj's Patriot Act episode about the Black Lives Matters protests that broke out in the wake of the murder of George Floyd, an African-American man. in the United States of America took place the police officers of Minneapolis. He also said that whenever he was called that word, people would laugh and he thought it was something funny and never thought about it much. He also subsequently posted an Instagram video saying he had messaged his teammates asking for an explanation before revealing the names of those calling him racist names.

Personally

Sammy grew up in a very religious household. His mother wanted him to be a pastor in the local Adventist Church. Sammy married Cathy Daniel in 2010. He has four children - Darren, Darjhan, Skai and Xzavier Reign. He founded the Darren Sammy Foundation which works with youth by, among other things, giving them scholarships.