The Celebreality Interview - Tailor Made
Nice guys finish…second? After earning the respect of very few after his time on I Love New York 2, that show’s winner arrived to I Love Money 2 with something to prove and little to lose. Below, the mastermind of the Underdog Alliance talks strategy in detail that will make your head swim. He also talks about his allegiance with It, his altercation with Buckwild, his image makeover and why Myammee was most deserving of the prize money.
I wouldn’t call you the master manipulator of I Love Money 2, but I think it’s fair to say that you were the head strategist. Can you sum up your philosophy regarding this game?
My strategy was to lay low. I felt that the alpha males would go at each other. Like Napoleon said, you lay back and let your enemies kill each other off. I did a lot of research. I didn’t watch much of I Love Money 1. I watched the first episode, but I did do a lot of reading about psychology and war strategy. 48 Laws of Power. So many of those are so relevant. [The contestant] It’s was “play a sucker to catch a sucker.”
It quoted that when I talked to him.
It’s learning. It’s amazing. We learn from each other. It’s so interesting, because I think people have a certain image of him, but because of the two of us come from such different backgrounds, we have such different perspectives. Sometimes, I’m overly analytical and he’s very common-sense. A lot of people try to stay he’s stupid, but a lot of the other players who I like, such as Cali or the Entertainer, a lot of their strategies were stupid. People would try to tell It to go in the box and he would say, “What are you talking about?” One of the rules is “never outshine your master,” so I actually made a point of playing down my intelligence and ability. When people feel you’re inferior, they feel like you’re less of a threat. One of the rules is “create a cult following,” and that became very easy, because the alpha males acted like an aristocracy and they thought everyone else were just pawns. Everyone says it and it gets so redundant, but this is a numbers game. It called me “Tailor Mandela” but it’s actually true. The majority was being oppressed by a few people, and all we needed to do was rally that majority and then it was so easy because we just got rid of the few. What I liked about our alliance is that all of us were relatively equal in strength. No one was weak, no one was strong. Whereas the other team had two or three figureheads that were super competitors and the rest of their squad was very weak. That’s not a good mix when it comes down to individual challenges.
After all that thinking and effort, were you disappointed to have gotten so far and lost?
I feel like I went into the last challenge as the favorite, whereas I went into the I Love New York 2 finale as the underdog. I like being the David versus the Goliath. When I got to the ice, instinct is that you go to the block that’s closest to you. The one in the center had its coin closer to the top. That’s fine. If I was strategic, if I was thinking everything through, I would have stopped and looked at each of them. But the way the challenge was set up was that it sort of evened the playing field. I feel like if I had been going up against a 20 Pack or a Buddha, I would have been in the second-place person at that point and I would have gotten the easier block of ice. Also, I might have pushed myself a little harder. While I was running, I said, “I’m just gonna pace myself.” Even when I was in the water, my concern was: don’t get lost. I felt I had a lead and all I needed to do was maintain that lead. Whereas if I were going against someone really strong, I would have had to drive myself that much harder. I wouldn’t have changed any strategy, but mentally, that needed to be my place. It’s hard to go against someone you like. If it’s someone I hate, I’m gonna use a lot more passion. Myammee, I liked her and I know she doesn’t talk about her personal situations, but I thought that of the Final 3, she was the most deserving.
Do you beat yourself up about it?
I do think of the ice part. Even the energy I put into melting the ice was not super strong. I felt like I had the lead and I was just playing it safe. When I turned around and she was getting the coin out, it was like, “What the hell?” She had more body fat, just as a woman, but I feel that I could have put more energy to it. I was pacing myself.
What was it about Myammee? You two seemed to stick together no matter what.
Actually, It was my closest ally from even before arriving on the scene. It and myself have been friends. I’ve visited him in the projects, I had talked to his mother on the phone. We were close. Now, we’re like best friends. They didn’t really play it up on the show, but we were trying to be like a duo coming into the house. But the point was not to make that evident.
Unlike everyone else, who announced when they were throwing challenges.
Yes. He was like my ace in the hole. We’d have little meetings on the side and I’d tell him, “Don’t worry. I got a plan. I got a plan A, B, C. Just lay in the cut.” He was getting concerned. And keep in mind that I had spoken with the Entertainer before going on the show, and he wanted to be in an alliance, but I felt like he was talking to everyone about being in an alliance. Unlike him, my goal was not to get rid of Buddha. If you save your enemy, they’re going to be so much more indebted to you than if you saved a friend.
Your alliance worked: four out of the Top 5 were part of it. What do you think was key?
When making a deal, so many people tried to bring up, “Oh, I did this for you. I did that for you.” At the end of the day, you have to appeal to people’s self-interest. That’s what our alliance was about. When 20 Pack got eliminated, he tried to say, “Our alliance was real friends!” We were just working together for a similar goal. It was a mutually beneficial relationship. We didn’t try to play that we all loved each other. We got along, but they key to it was mutually beneficial. Everyone worked together, and the reason the alliance worked is because it made sense.
What was it about Myammee, though, to return to a previous question?
In watching back, I now see that she was just as interested in getting rid of me and It as the other two girls were. I think Ice was the most aggressive. Prancer and I are friends, and I felt that I related to her really well. Once we got rid of Ice, I knew Myammee would be indebted to me, because I saved her. Myammee was terrified. The night before, she had written “Bitch” on Saaphyri’s check in red ink. There was already bad blood. In the next elimination, when Prancer was Paymaster, I worked so hard to convince Saaphyri to let It vote the way I wanted him to. Saaphyri went into the box willingly, which basically got rid of Frenchie. But Saaphyri didn’t want Frenchie to know that, so we made It look like the turncoat, but Saaphyri was totally in on the deal. I was very proud of how persuasive I was, that I could convince someone to go in the box on their own.
My head starts spinning when I think of all this stuff. This second season is complicated.
Like I said, I didn’t watch the first season. I don’t watch any reality other than…
What you’re on?
…what I’m on. I know that makes me sound like a narcissist. I’ve watched early seasons of Survivor and The Apprentice, and I feel like this show is so much more strategic than Survivor. Survivor is just about two alliances. Here you have this dynamic where three people go in the box, as chosen by your team, but the other team chooses who goes home. So you have to straddle the fence between having the other team liking you enough, and not having your own team hate you. After seeing Onix go home the second night, though, I realized that you have to put a stake in the ground and let your position be known. I never committed to Buddha, but I did come to like him. One thing you don’t get to see is that Buddha, myself, Ice and Bonez, we’d go up to bed at a reasonable time and read books. The Entertainer, 20 Pack, they’d party like frat boys and get drunk. Buddha is a very disciplined individual. He’d go for a run every morning. It requires discipline to have that kind of body. He and I use a little more discretion in terms of the women we’re with. We aren’t like the Entertainer, who basically will get with every girl there is. Not that I look down on people who are overly promiscuous. There were a lot of beautiful girls there, but I was focused on the game.
You might say that you had a “like alliance” with It.
My alliance with Kwame is really what got me to the end. His was the vote that got Frank in the box. I never was in the box until the final episode, and Kwame was always the decisive vote. I would say that he played the game just as well as I did. He got to come to the challenges drunk. He was in the box, but he never went home. I know Prancer said he was riding my coattails, but I don’t think so. His votes were decisive, and I knew he’d never vote against me.
What about negotiating with 20 Pack? Why did you even entertain him?
Going into the show, my reputation preceded me, and everyone thought, “This guy’s a snake. This guy’s a backstabber.” After 20 Pack was eliminated, he shook everyone’s hand and then he came back and looked at me and was just like, “Damn. I shoulda known you would screw me.” I really felt bad about that. I felt bad that whole night, I could barely sleep, but I did have a dream that Saaphyri was Paymaster. I told Angelique about it, and I wish they would have kept that, because it was like I had a prophecy. Also, 20 Pack was acting like a shield for me. That’s why the Entertainer’s strategy was silly. “No Buddha. No Buddha. No Buddha.” OK, Buddha’s gone, what’s next? You.
What was your take on Saaphyri flirting with you?
When I got into the house, I felt it was an important to form an alliance with Buddha, so I was determined to get the bed right next to him. Saaphyri and Buckwild were trying to get me to stay with them. They didn’t want Leilene in their room. They were flirting with me, and I was like, “Forget that.” After the Under the Bus challenge, when I wanted 20 in the box and I went to talk to Saaphyri about it, she asked me if I liked chocolate and was saying all this gross stuff to me. She was very manipulative.
What about the incident with Buckwild? She accused you of choking her.
I was in the bedroom and Buckwild was running around, trying to terrorize everyone. She was in Prancer’s face, screaming at her. I really respect Prancer for exercising such self-control. Buckwild came over to my bed, she started throwing my clothes around and I just went to get her away from them and all of a sudden she started screaming, “He’s choking me!” I saw the clip of what happened after that and she was in the bathroom laughing hysterically. One thing that Saaphyri and Buckwild have in common is that there’s no lie they’re unwilling to tell. Don’t say someone’s choking you if they’re not. That’s defamation of character.
So you did not choke her?
No. Absolutely not. I think Buckwild dumbs herself down to make her persona what it is. She’s smart, but she’s so focused on fame that she doesn’t care about its cost. All she knows how to do is fight and yell. I feel that she should have more respect for herself to realize that people will like her for being things other than a screaming, yelling lunatic. She thinks that’s the only way she can be noticed. There are a lot of people like that. Once on set, Heat said to me, “Man! We’re on six episodes! This is huge! Think of how many club appearances!” I focused on the game, but so many people were focused on building their character. The audience can really see through that.
Any thoughts on your ex, New York?
I wish her the best. She recently reached out to a mutual friend and asked for my number. I told him it was okay to give it to her. Although I am currently in a relationship and have no interest in reconciling with her romantically, I wish nothing but the best for her. I will always be here for her as a friend.
She blames you for your breakup.
Oh, OK.
She says you became entranced with fame and once you achieved it, you no longer needed her.
Tiffany has a jealous streak. I couldn’t take her to a party without her making assumptions about what it meant. Like, “Oh, you like girls that are like those over there? That’s why you brought me here?” Suffice to say, there’s more to the story than she lets on or than what you saw on New York Goes to Hollywood.
You talk about other people building their characters, but I feel like you changed yours considerably. Do you feel redeemed via Money?
I wasn’t happy with my reputation from I Love New York. I don’t regret anything I did on that show because it was all for Tiffany. I’m the type of guy whose girlfriend is always my best friend, and I’ve never had too many guy friends, anyway. So I didn’t care about the guys on that show. But because of that, I earned a reputation as a snake and back-stabber. On this show I went in wanting to be strategic and wanting to do it intelligently, but also wanting to keep my honor. And I think I did that.
Keep up with Tailor Made via his MySpace and also, check out his new improvised video project with It.
Related content
I Love Money 2 show page
I Love Money 2 full episodes, show clips and bonus scenes



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May 7th, 2009 at 12:19 am
I would like to see Tailor Made get his own show.
I was extremely torn. I’m glad Myamme won, but I would
have been pleased if Tailor Made or Prancer had won.
I miss the show already.
Very good interview, very smart man.
May 7th, 2009 at 3:29 am
I liked Tayor made on both ILNY2 and ILM2. On both shows everyone called him a snake, but really he was smart and probably the most genuine on both shows.
Great Interview!!!!! Very Informative and great info of stuff behind the scenes we did not know.
May 7th, 2009 at 5:14 am
would someone please tell tailor made that her name is pronounced SAA-PHY-RI. not SA-FA-RI. i found myself wanting to see him gone so he would stop butchering her name!
May 7th, 2009 at 1:11 pm
I think you are a very intellectual man and i really respect you for that. I love your persona and you were my favorite guy on the show. Keep doing what your doing.
May 7th, 2009 at 1:32 pm
Tailor is the master. very smart man!
May 7th, 2009 at 5:20 pm
Wooooooow! He is a smart guy. They didn’t see him coming at all. *lol* He laid low and outstrategized them all to make it to the final three (and the other two were a part of his alliance).
D*a*m*n, if people like the Entertainer & Heat could read they would be ashamed of themselves after learning that Tailormade played them like a piano.
May 7th, 2009 at 10:54 pm
I would really like to see TM get his own show as well…
May 7th, 2009 at 11:30 pm
At first, I didn’t like TM at all, but after watching NYG2H and ILM2, he seems not a bad person at all. Plus he and It should have their own show!!! I LOVED Em!
Episode 2 is coming soon
May 8th, 2009 at 4:22 am
Tailor Made’s strategy is to be commended. If it was not for “IT” and Tailor Made Myammme would not have won. Myammme needs to have some insight into the times when “IT’s” and tailor Made’s vote kept her around. No one could have won without protection. Very clever Tailor Made and “IT”. The show is truly strategy. I also liked a Fox show called, “Paradise Island but I Love Money is much more entertaining because it has humor and more personality. Please do a third season and bring back the Entertainer until he finally wins and moves out from his parents. Then there can be a reality show with him spending the $250,000.
May 8th, 2009 at 4:25 am
By the way….loved loved loved “The Odd Couple” with “IT” and Tailor Made. Funny! Looking forward to a series on VH1.
May 8th, 2009 at 11:40 am
By far the best interview ever!
Hope to see more of you in future shows!
May 8th, 2009 at 12:11 pm
I love Tailor Made. I think he should be with New York. It doesn’t matter though, as long as he’s happy.
May 8th, 2009 at 12:29 pm
“I think he should be with New York. It doesn’t matter though, as long as he’s happy.”
Are you out of your effin mind?!! TM is happier without NY in his life. Besides he is too smart for NY! She’s a dummy and I’m glad he dumped her azz!
Can you imagine him trying to have a decent intellectual conversation with her while she’s busy screaming obscenities at him and everyone within 50 feet! LMAO
And that’s the truth. We all know it!!
May 9th, 2009 at 12:06 am
u suck u suck u suck tailor made i am so glad that u did not win u r a wussy and u ruind my alliance and at the end of the day u did not deserve that money u a little ~~)$!+&*&$&%_*_+*
May 9th, 2009 at 7:35 pm
Talior made is stupid and a snake also thank god he didn’t win the money he didn’t deserve it and he broke up the best alliance!
May 9th, 2009 at 7:51 pm
Tailor Made is the F**king master right now!
May 9th, 2009 at 11:29 pm
Tailor Made is a smart man and he stands out in this silly, but fun, genre of television. I liked how Myammee choked up while giving him his check, saying he’d been the only one to stick by her side. Who’s he dating, anyway? Oh, did he win any cash for his efforts? Good luck, Tailor Made!
May 9th, 2009 at 11:30 pm
one more thing: good interview.
May 11th, 2009 at 6:51 pm
i love tailor made.
always have.
May 11th, 2009 at 10:54 pm
i love this guy!!!!!!!!!!!!!!
May 12th, 2009 at 10:15 am
marry me tailor!!!!
May 12th, 2009 at 10:21 am
Majority Rules, the numbers are there. GIVE THE MAN HIS OWN SHOW!!!
May 13th, 2009 at 1:41 am
I hate the way all your cast mates are hating (other alliance)
May 21st, 2009 at 12:17 am
I just love Tailor Made. I never watched any of the I Love NY or Flav shows, so I only knew about Angelique when ILM2 premiered. Tailor Made was my favorite, other than Frenchie, just b/c it was clear he was very intelligent from the very beginning. Everything he would say was what I was thinking. I hated people calling him a snake, although I know it’s simply a reflection of themselves. He was so genuine and so loyal to his word. He was never arrogant. I really wanted Tailor to win, and It was my second choice of the three, but I’m so happy for Myammee. Her reaction to the win just showed how much it was about bettering her situation than pride.
I always loved Angelique on ROL (and still on ILM2), because she is so genuine and loyal. She may be a freaky girl and loves to be nekkid, but she’s a very good person and is comfortable enough with herself that she makes no apologies. She has such integrity. That’s character.
May 21st, 2009 at 7:35 am
I will like you guyz to connects me with Myammah and saaphari to date on date cos i have crush on them. My mail address is badru9@yahoo.com