Paddy Brennan's Countdown to Cheltenham: 5 DAYS TO GO - Konfusion & Regent's Stroll Among Handicap Fancies

With the Cheltenham Festival just a five days away, Gold Cup-winning jockey Paddy Brennan has turned his attention to this year's handicaps, the races that, as he puts it, can define a whole week, while delivering some welcome news on the state of the track.
Find out what Paddy had to say just days away from that iconic Cheltenham roar, with Free Bets, the home of the the best Cheltenham Betting Offers.
"The Nicest Ground Cheltenham Has Seen for a Long Time"
Ahead of the meet, Paddy encourages punters to understand just how significant the ground conditions can be on the entire week. After a wet January and February, a spell of dry, mild weather has transformed the Cheltenham track, and Paddy, who lives just ten minutes from the course, has been watching it closely.
"I think it'll be the nicest ground Cheltenham has seen for a long, long time," he said. "We've had all that rain all the way through January and February, suddenly we've got this colour coming in, the grass is green, healthy, natural. Sometimes you have a cold winter and they have to water from as early as mid-February, whereas we don't have that this year."
The significance of that extends well beyond aesthetics. Brennan was clear that the drying ground has a direct bearing on several of the most interesting handicap contenders this week, and he factored it into almost every selection.
Fred Winter: Winston Junior an Eye-Catcher
Brennan had little hesitation in the Fred Winter, pointing to Winston Junior as the standout on the basis of how connections have managed him all season.
"If you're thinking which horse has the best chance from the outside looking in, it's in the Fred Winter," he said. "They haven't overrun him. They know he's good. This is the race, you want something that's just been protected all season, not a horse that's had to work hard all winter just to get a mark to get in. Winston Junior is exactly that."
Paddy's Pick: Winston Junior - 6/1 with bet365
Ultima Handicap Chase: Konfusion a Massive Player
The Ultima is the race Brennan kept returning to across the session and his selection was not one of the two market leaders from the Oliver Greenall and Josh Guerriero yard.
While he leaned towards Iroko over stablemate Jagwar: "I questioned Jagwar's resolution a little that day at trials, he didn't go on and win when he should have", meaning it was Konfusion, trained by Joel Palkinson and Sue Smith, that he identified as his each-way play at 16/1.
"That's one I think about a lot. That's been the plan for some time," he said. "He'll be up front, plenty of room, he could just take a bit of beating. In a race like the Ultima, you only need one mistake or a bit of bad luck in running, there's always traffic with so many runners. That's why I like Konfusion. Up front, out of all that, he could take a bit of beating."
On Handstands, who has been talked up by trainer Ben Pauling, Brennan was measured: "He goes around with his head up, there's a big difference between him and Jukebox Man to me, anyway. I think he's high enough in the weights."
Paddy's Pick: Konfusion (Each-Way) - 16/1 with bet365 (4 places)
Pertemps: Supremely West, But Only If the Rain Returns
Brennan has been associated with the Dan Skelton yard in work this season, and that inside knowledge gives his assessment of Supremely West particular weight. His view is nuanced, and the ground caveat he raised this week is a timely one.
"If you look at him in his work, you wouldn't back him at 10s or 15s. He's not a workhorse, he's slow," he admitted. "But I reckon when he gets into a race, it's different. Harry is very sweet on him, he thinks he'll win. My only question mark is if it keeps drying up, he does appreciate a bit of slower ground and he would need the race to slow down a bit."
Given Brennan's earlier assessment that the ground is drying out significantly, that is a caveat worth heeding. At a price that has shortened considerably in recent days, punters would do well to keep one eye on the forecast.
Paddy's Pick: Supremely West - 9/2 with Ladbrokes (With a ground caveat)
The Cup: Jingko Blue the Each-Way Interest
Paddy admitted the bet MGM Cup, formerly the Coral Cup, is not a race he studies in great depth, but one name did stand out: Jingko Blue.
"I like Jingo Blue, I was really impressed with how he ran against Kabral Du Mathan at Cheltenham on New Year's Day," he said. Beyond that, he was candid about the difficulty of the race: "There's a chance for anyone winning that. It doesn't look like there's something that's clearly been chucked in."
He was less charitable about some of the market principals, notably Kopeck De Mee: "How is he [Kopek De Mee] still at the top of the betting? He's done nothing but let people down and he's still a talking horse."
Brennan's interest: Jingko Blue (Each-Way) - 16/1 with Unibet (4 places)
Jack Richards Handicap Chase: Regent's Stroll & Meetmebythesea
Brennan singled out Regent's Stroll as the horse he would most want to ride in the Jack Richards, with a straightforward case built around his travelling and jumping ability.
"He'll travel, he'll jump, and if he does everything right he'll be hard to beat," he said. "I'd love to ride him, he's the type that if everything clicks, he's hard to beat in a race like this."
However, the more intriguing angle may be Meetmebythesea, trained by Ben Pauling and owned by JP McManus, who has been shortening significantly in the market, from 14/1 to around 6/1 in recent days.
Brennan explained why: "The only reason he ran in the Game Spirit was to qualify for this race. So you've got to completely ignore that run, if you go on the run before, he'd probably be favourite. This is a good race."
Paddy's Pick: Regent's Stroll 6/1 with Virgin Bet & Meetmebythesea - 11/2 with bet365 (Market mover to note)
Grand Annual Chase: Ryan's Rocket for Fergal O'Brien
In what Paddy describes as the maddest race of the week, "a Champion Chase on Nissan Micra's," as Paddy put it, he pointed to Ryan's Rocket as his selection, with the ground and course suiting the horse well. "I think he loves the ground, loves the track. He'd be good for Fergal."
On Sixmilebridge, who looks bound for the Jack Richards, he acknowledged the class but flagged fitness concerns: "Grade one horse in a handicap, but he loves soft ground and has had a busy winter. He'll need things to slow down."
Paddy's Pick: Ryan's Rocket (Each-Way) - 8/1 with bet365 (4 places)
Martin Pipe: A Lottery Worth Celebrating
Brennan was characteristically generous in his assessment of the Martin Pipe, a race he sees as vital to the wider health of the sport even if it resists easy analysis.
"It's a lottery race, but a great one for those lads," he said. "It's tough to get rides at Cheltenham this week for jockeys. You can send 22 or 23 jockeys out there with a chance, that's how I started off. It's brilliant that they have a race like that. Willie and Gordon and Dan get the headlines, but it's important to keep the next generation coming through."
On his fancies, he was supportive of A Pai De Nom, of the Skelton yard, without being emphatic: "He's solid. But it's a lottery race."
Paddy's Pick: No Bet
Paddy Brennan's Cheltenham 2026 Summary
| Race | Selection | Notes |
|---|---|---|
| Supreme Novices' Hurdle | Old Park Star | Banker of the meeting |
| Arkle | Kopek Des Bordes | Lack of chasing experience, only weakness |
| Juvenile | Winston Junior | Not been overworked, comes in off a good mark |
| Ultima | Konfusion | Massive chance, great EW value |
| Champion Hurdle | Golden Ace | Wide-open race, she makes her own luck |
| Plate | No Bet | Notes Madara and McLaurey as players, but not great value |
| National Hunt Chase | No Bet | Nothing stands out, so will sit out |
| Turners Novices' Chase | No Drama This End | More heart than head with this one |
| Brown Advisory | Wendigo | One of my bankers |
| The Cup | Jingko Blue | Impressed on New Years, 20/1 is good EW value |
| Cross Country | No Bet | Between the two favourites, hard to pick apart |
| Champion Chase | L'eau Du Sud | Best placed horse to capitilise if Majborough makes a mistake |
| Grand Annual | Ryan's Rocket | A great chance for Fergal O'Brien |
| Bumper | No Bet | Very little to go off |
| Mares Novice Hurdle | Bambino Fever | Short, but potential banker |
| Jack Richards | Regent's Stroll | The one I'd want to be on |
| Mares Hurdle | Lossiemouth | It's her race, if she goes she'll win again |
| Stayers Hurdle | Ma Shantou | Ticks all the boxes, Cobden on board an added bonus |
| Ryanair Chase | Fact To File | If he goes, he wins. Simple. |
| Pertemps | Supremely West | If he gets his ground! |
| Kim Muir | No Bet | JP will most likely have a winner, but which one? |
| Triumph Hurdle | Maestro Conti | Maestro Conti to win, One Horse Town (EW) the play for value |
| County Hurdle | No Bet | Hard to pick a winner |
| Mares Chase | Panic Attack | Most improved Mare this season |
| Albert Bartlett | Money Garrow | Massively undervalued in the market |
| Gold Cup | Haiti Couleurs | The one I'd want to be on in the biggest race of the Festival |
| Hunters Chase | No Bet | Like a few, but no strong opinion on this race |
| Martin Pipe | No Bet | Impossible to predict until final declarations |
The Bigger Picture: "There's a Goalkeeper This Year"
Brennan closed with a summary that captures the mood of the week perfectly. In his view, this is the most open, competitive Cheltenham in years, and the handicaps reflect that as much as the Grade Ones.
"Last year there were penalty kicks for Willie and Gordon with no goalkeeper. Well, there's definitely a goalkeeper standing there this year. Bar the Ryanair, every race this year is going to have to be earned, every horse, jockey, trainer and owner is going to have to go and earn it. I think even Willie and Gordon know they're coming into a much more competitive meeting. And that's what makes Cheltenham what it is."

Paddy Brennan is a retired National Hunt jockey and six-time Cheltenham Festival winner, best known for his 2010 Gold Cup victory aboard Imperial Commander. Since retiring in 2024, he has remained influential through punditry and racing analysis.
