Retired - Retired after 2016 season
- Birthdate: 05/07/1990
- Drafted (NBA): 51st pick, 2013
- Pre-draft team: Oklahoma
- Country: USA
- Hand: Right
- Agent: -
| Date | League | Transaction |
|---|---|---|
| 2013 NBA Draft | NBA | Drafted 51st overall by Orlando. |
| 27th September, 2013 | NBA | Signed a partially guaranteed three year contract with Orlando, for $682,180 in the first season and the final two seasons at the minimum salary. |
| 25th October, 2013 | NBA | Waived by Orlando. |
| 1st November, 2013 | D-League | Designated as an allocated player by Fort Wayne Mad Ants. |
| 4th November, 2013 | D-League | Traded by Fort Wayne Mad Ants to Maine Red Claws in exchange for Terrance Henry and Xavier Silas. |
| 25th July, 2014 | France | Signed a one year contract with Le Mans. |
| 26th November, 2014 | France | Left Le Mans. |
| 29th January, 2015 | D-League | Designated as a returning player by Maine Red Claws. |
| 21st April, 2015 | Puerto Rico | Signed for the remainder of the season with Mayaguez. |
| 25th May, 2015 | Puerto Rico | Left Mayaguez. |
| 28th July, 2015 | France | Signed a one year contract with Nanterre. |
| 8th October, 2015 | France | Left Nanterre. |
| 20th October, 2015 | Israel | Signed for the remainder of the season with Maccabi Rishon. |
| 7th December, 2015 | Israel | Left Maccabi Rishon. |
| 7th December, 2015 | Israel | Signed for the remainder of the season with Maccabi Kiryat Gat. |
| 31st December, 2015 | Israel | Left Maccabi Kiryat Gat. |
| 2008 - 2010 | Mississippi State (NCAA) |
| 2010 - 2013 | Oklahoma State (NCAA) |
| July 2013 | Orlando Magic (Summer League) |
| September 2013 - October 2013 | Orlando Magic (NBA) |
| November 2013 | Fort Wayne Mad Ants (D-League) |
| November 2013 - June 2014 | Maine Red Claws (D-League) |
| July 2014 | Orlando Magic (Summer League) |
| July 2014 - November 2014 | Le Mans (France) |
| January 2015 - April 2015 | Maine Red Claws (D-League) |
| April 2015 - May 2015 | Mayaguez (Puerto Rico) |
| July 2015 | Indiana Pacers (Summer League) |
| July 2015 | D-League Select (Summer League) |
| July 2015 - October 2015 | Nanterre (France) |
| October 2015 - December 2015 | Maccabi Rishon (Israel) |
| December 2015 | Maccabi Kiryat Gat (Israel) |
July 4, 2014
Romero Osby - After being cut by the Magic last training camp, Osby is back for a second go, despite the power forward spot he plays being even fuller than it was last time with the addition of Gordon and the breakout of the sneakily good Kyle O'Quinn. In the year hence, he has been in the D-League with the Maine Red Claws, where his task was to rein in his mistake making. He failed. Although he poured in 16.2 points and 6.4 rebounds in only 27 minutes a game, there were also 3.3 fouls and 2.8 turnovers per game in that time. A quality offensive talent, Osby still does not know how to use what he has. He can use summer league as an opportunity to showcase what he does have, at least, as well as prove his return to health after season ending shoulder surgery in January.
December 12, 2013
Romero Osby - Drafted by the Magic, Osby was squeezed out of the roster shuffle, and now finds himself in the D-League, where he averages 15.6 points and 8.4 rebounds in only 29 minutes per game for the Maine Red Claws. However, he also averages 4 turnovers a game and is shooting 38% from the field. He has tools, but is caught between positions and needs to find an identity.
July 9, 2013
Romero Osby
Osby makes things happen, good and bad. Normally, this is an underrated positive attribute in a player - genuine productivity is often overlooked by the risk-averse nature of basketball coaches and executives, and mistakes seem to linger in the memory moreso than positive play ever could. In Osby's case, however, the mistakes are so plentiful, and other holes significant enough, that the reconciliation is difficult. Offensively, Osby provides a bit of everything - strong, and decently if not overly athletic, Osby is a runaway train in transition, can drive the ball, finish around the basket with some post-up play to boot, and is ever developing a jumpshot with three point range. However, this bullishness and relentless aggressiveness is accompanied by extremely high turnover numbers - bad decision making, a limited passing game, and strength rather than nuanced body control, all combine to make Osby unreliable, no matter how valuable his scoring can be. Furthermore, Osby rather underwhelms on the glass, has demonstrated little out of pick and roll situations (although being in a situation with better guards to run it may change this), and only sporadically defends both the interior and perimeter. Osby's offensive talents are intriguing, but the total package is frustrating.