Ranking 2 Time Winner Attempts in CBS Big Brother
S
A
B
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Created Mar 31, 2026
So this is my ranking of big brother contestants who won a season then returned on a subsequent season. There are only 8 players to have done this as of BB27, which really amounts to 7 actual attempts when you consider Dick's BB13 game. I think prior to my ranking it is also relevant to clock three major factors influencing with these attempts.
(1) No player has won a season, come back for a subsequent season, and then been invited back for another season. It seems like CBS wants to keep this as a "1 and done" situation at present, as many other players have played 3 seasons in a relatively short time frame, 1 of which is on the list. I think at present we just don't have enough seasons per year to make it plausible for CBS to bring back a former winner for a "second" comeback.
(2) Most of these players (besides Rachel and Will) played their returnee winner season alongside another returnee winner. I do not think this is a coincidence, as you can match the three pairs fairly easily. This made my ranking a lot easier, as each season like this (BB13, BB14, BB22) has one player who played a better game than the other. So my rankings mostly came down to placing these three "predetermined comparisons" in alignment with the games of Rachel, Will, and the other 2 sets. Hopefully that makes sense, although I understand it probably doesn't. I do, however believe production did this intentionally, perhaps as a sort of 'unspoken' Grodner rule that when one winner comes back, another should also be there as a foil. This theory goes out the window for BB27, but BB27 is quite late on the timeline of Grodner's production of the show, and things can change in the 3-5 year gaps we have seen in the modern era between returnee seasons. The most convincing thing to me about this comes from thinking back to the voting system of BB7. The larger voting pool for cast mates alludes to us that production had slated a second winner to potentially join Will on BB7, the winner of BB3, Lisa. Maybe CBS assumed she would get on, maybe they didn't. But it supports the theory of "Winner Foils" being present on returnee seasons, including former winners. Hopefully going forward this trend ceases, and the appearance of Rachel as a BB11/BB19 Paul/Jessie style solo returnee was certainly a deviation from this perceived path.
(3) The reason no big brother player has ever won twice is not due to a lack of skill or selecting the wrong returnees, but rather due to CBS's sporadic infrequency in casting returnees. Take Rachel for example, who basically would have said yes to any returnee season from BB13 through BB27. She even petitioned to have her sister, BB15 diva Elissa compete for her as a duo while she was pregnant in 2020. Yet, for such an icon of the game, who is a contender for the mount rushmore of the game, she has only played 3 times. The same can be said for other icons of the game who are not opposed to returning, such as Nicole, Janelle, and Da'Vonne. As for Da'Vonne, she is tied for the second most appearances on big brother with 3, yet she has also appeared on the Challenge 3 times, where she is far from the second most cast Challenge contestant. Other shows like survivor and MTV the Challenge have players who have returned 5, 8, 13, or even approaching 20+ times on the same show. Both the aforementioned shows also have about twice the seasons as Big Brother (if you include the 5 all stars seasons for MTVtC), yet have been on air for the same 25-30 year time period. CBS has become lazy (especially in the modern era) when it comes to casting, relying more and more on the standard "fresh cast of newbie players", which is the beloved format of many longtime and casual fans. Yet, one thing I believe these fans can fail to notice is the causation of this casting style, resulting in an uptick in recruited players (who know nothing about our beloved [at times] franchise), and seasons lacking strategic prowess and historical knowledge about the show.
Above all, I think it is time grodner give the fans what the want: a creative casting theme involving players of the past. Not 1 or 4 players from the past, but a solid number of players from the past, without creating a "small Stars" atmosphere. I personally think that BB13 got it right in this regard, albiet with a few less rookies than it required. A season with 6 returnees, who have their own internal dynamics, mixed with a group of 10 newbies keeps the pre-gaming issues we saw in BB22 at bay, while still giving the game the requisite influx of players who understand what the F is going on. I look back on seasons like BB13, BB14, and BB18 as the embodiment of this formula. Thats just my opinon, but enjoy the ranking of the 8 aforementioned players below.
(1) Dan [Best to do it, closest we have come to a 2 time winner, acheieved on BB14, likely never going to return sadly]
(2) Rachel [Really hard to rank, but I think she deserves the benefit of the doubt, not evicted on her return run in BB27]
(3) Will [Just below Rachel, prob could have been an S tier if he has played his relationship with Janelle better]
(4) Nicole [Even if you do not like her or the BB22 game, she did solid. Several small misplays are why she lost]
(5) Jordan [Easiest pathway to a second win, but heavily influenced by production, Pandora's box, Jeff, and Dick's leave]
- Biggest "what if" in the game's history. Would be interesting to have a relatively low skill winner become the only 2 timer
(6) Boogie [Made moves and alliances, overplayed, shouldn't have evicted Janelle, better than BB22 Ian ]
(7) Ian [Worst performance by a returning player who wasn't removed from the game in the first week]
(8) Donato [This one makes me sad, we were truly robbed of a Dick return and will likely never see him play again outside of a hypothetical all winners season, but even then its not like the franchise doesn't have 8 or 10 other male winners they would call back prior to Dick. While his exit from the game certainly benefitted Danielle's game, it puts the ranking of both Rachel and Jordan into question as to whether things would have played out differently had he been able to play]
(9) F Tier [I think there is potential for a returning winner to do much, much worse than Ian or Dick, we just haven't seen it yet. Imagining the winners of BB3, BB9, BB17, BB21, or BB25 coming back for a hypothetical second run, it is likely several of them would do worse than BB22 Ian and potentially even worse than Dick's (brief yet honorable discharge) from BB13. At least Dick was removed from the game for outside circumstances, rather than poor gameplay or blowing up his position. ]
Also in the image it has Will after Nicole, and Boogie after Ian, but just ignore that. the image only accuarately places them in the correct box. I am a longtime fan who came into the show around BB12, when I was 10. I have seen every season once, and most twice, with several seasons 3+ times. I am definitely partial to the women on the list, but I tried to rank them without my own personal bias (but that is impossible which I am recognizing here). Please don't be mad at me or throw a fit -- this a internet list by a 20 something law student made in my (fleeting) free time. If you disagree I would love to hear your ranking in the comments!!! It is likely this list will be torn apart in the comments and please by all means tear it apart. My main hope is that my three points resonate with fans, as I have been thinking about this subset of returning players and the challenges associated with them for some time now. If you really are big mad and want to 'get' me for making this list and disrespecting the game of Will or something, then my advice is to maybe touch grass idk. Enjoy!
Just food for thought! What do you think?
(1) No player has won a season, come back for a subsequent season, and then been invited back for another season. It seems like CBS wants to keep this as a "1 and done" situation at present, as many other players have played 3 seasons in a relatively short time frame, 1 of which is on the list. I think at present we just don't have enough seasons per year to make it plausible for CBS to bring back a former winner for a "second" comeback.
(2) Most of these players (besides Rachel and Will) played their returnee winner season alongside another returnee winner. I do not think this is a coincidence, as you can match the three pairs fairly easily. This made my ranking a lot easier, as each season like this (BB13, BB14, BB22) has one player who played a better game than the other. So my rankings mostly came down to placing these three "predetermined comparisons" in alignment with the games of Rachel, Will, and the other 2 sets. Hopefully that makes sense, although I understand it probably doesn't. I do, however believe production did this intentionally, perhaps as a sort of 'unspoken' Grodner rule that when one winner comes back, another should also be there as a foil. This theory goes out the window for BB27, but BB27 is quite late on the timeline of Grodner's production of the show, and things can change in the 3-5 year gaps we have seen in the modern era between returnee seasons. The most convincing thing to me about this comes from thinking back to the voting system of BB7. The larger voting pool for cast mates alludes to us that production had slated a second winner to potentially join Will on BB7, the winner of BB3, Lisa. Maybe CBS assumed she would get on, maybe they didn't. But it supports the theory of "Winner Foils" being present on returnee seasons, including former winners. Hopefully going forward this trend ceases, and the appearance of Rachel as a BB11/BB19 Paul/Jessie style solo returnee was certainly a deviation from this perceived path.
(3) The reason no big brother player has ever won twice is not due to a lack of skill or selecting the wrong returnees, but rather due to CBS's sporadic infrequency in casting returnees. Take Rachel for example, who basically would have said yes to any returnee season from BB13 through BB27. She even petitioned to have her sister, BB15 diva Elissa compete for her as a duo while she was pregnant in 2020. Yet, for such an icon of the game, who is a contender for the mount rushmore of the game, she has only played 3 times. The same can be said for other icons of the game who are not opposed to returning, such as Nicole, Janelle, and Da'Vonne. As for Da'Vonne, she is tied for the second most appearances on big brother with 3, yet she has also appeared on the Challenge 3 times, where she is far from the second most cast Challenge contestant. Other shows like survivor and MTV the Challenge have players who have returned 5, 8, 13, or even approaching 20+ times on the same show. Both the aforementioned shows also have about twice the seasons as Big Brother (if you include the 5 all stars seasons for MTVtC), yet have been on air for the same 25-30 year time period. CBS has become lazy (especially in the modern era) when it comes to casting, relying more and more on the standard "fresh cast of newbie players", which is the beloved format of many longtime and casual fans. Yet, one thing I believe these fans can fail to notice is the causation of this casting style, resulting in an uptick in recruited players (who know nothing about our beloved [at times] franchise), and seasons lacking strategic prowess and historical knowledge about the show.
Above all, I think it is time grodner give the fans what the want: a creative casting theme involving players of the past. Not 1 or 4 players from the past, but a solid number of players from the past, without creating a "small Stars" atmosphere. I personally think that BB13 got it right in this regard, albiet with a few less rookies than it required. A season with 6 returnees, who have their own internal dynamics, mixed with a group of 10 newbies keeps the pre-gaming issues we saw in BB22 at bay, while still giving the game the requisite influx of players who understand what the F is going on. I look back on seasons like BB13, BB14, and BB18 as the embodiment of this formula. Thats just my opinon, but enjoy the ranking of the 8 aforementioned players below.
(1) Dan [Best to do it, closest we have come to a 2 time winner, acheieved on BB14, likely never going to return sadly]
(2) Rachel [Really hard to rank, but I think she deserves the benefit of the doubt, not evicted on her return run in BB27]
(3) Will [Just below Rachel, prob could have been an S tier if he has played his relationship with Janelle better]
(4) Nicole [Even if you do not like her or the BB22 game, she did solid. Several small misplays are why she lost]
(5) Jordan [Easiest pathway to a second win, but heavily influenced by production, Pandora's box, Jeff, and Dick's leave]
- Biggest "what if" in the game's history. Would be interesting to have a relatively low skill winner become the only 2 timer
(6) Boogie [Made moves and alliances, overplayed, shouldn't have evicted Janelle, better than BB22 Ian ]
(7) Ian [Worst performance by a returning player who wasn't removed from the game in the first week]
(8) Donato [This one makes me sad, we were truly robbed of a Dick return and will likely never see him play again outside of a hypothetical all winners season, but even then its not like the franchise doesn't have 8 or 10 other male winners they would call back prior to Dick. While his exit from the game certainly benefitted Danielle's game, it puts the ranking of both Rachel and Jordan into question as to whether things would have played out differently had he been able to play]
(9) F Tier [I think there is potential for a returning winner to do much, much worse than Ian or Dick, we just haven't seen it yet. Imagining the winners of BB3, BB9, BB17, BB21, or BB25 coming back for a hypothetical second run, it is likely several of them would do worse than BB22 Ian and potentially even worse than Dick's (brief yet honorable discharge) from BB13. At least Dick was removed from the game for outside circumstances, rather than poor gameplay or blowing up his position. ]
Also in the image it has Will after Nicole, and Boogie after Ian, but just ignore that. the image only accuarately places them in the correct box. I am a longtime fan who came into the show around BB12, when I was 10. I have seen every season once, and most twice, with several seasons 3+ times. I am definitely partial to the women on the list, but I tried to rank them without my own personal bias (but that is impossible which I am recognizing here). Please don't be mad at me or throw a fit -- this a internet list by a 20 something law student made in my (fleeting) free time. If you disagree I would love to hear your ranking in the comments!!! It is likely this list will be torn apart in the comments and please by all means tear it apart. My main hope is that my three points resonate with fans, as I have been thinking about this subset of returning players and the challenges associated with them for some time now. If you really are big mad and want to 'get' me for making this list and disrespecting the game of Will or something, then my advice is to maybe touch grass idk. Enjoy!
Just food for thought! What do you think?