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A supporter of the [[Mexican–American War]], Breckinridge sought appointment to the staff of [[William O. Butler]], but Butler could only offer him an unpaid aide position and advised him to decline it.<ref name=heck20>Heck, p. 20</ref> In July 1847, he delivered an address at a mass military funeral in Frankfort to honor Kentuckians killed in the [[Battle of Buena Vista]], during which [[Henry Clay]], whose [[Henry Clay, Jr.|son]] was among the dead, wept.<ref name=klotter103>Klotter in ''The Breckinridges of Kentucky'', p. 103</ref> The oration inspired Theodore O'Hara to write ''The [[Bivouac of the Dead]]''.<ref name=klotter103 />
Breckinridge again applied for a military commission after [[William Owsley]], then governor of Kentucky, called for two additional regiments on August 31, 1847.<ref name=heck21>Heck, p. 21</ref> Owsley's advisors encouraged the Whig governor to commission at least one Democrat; [[John J. Crittenden]] supported Breckinridge's application.<ref name=davis34>Davis, p. 34</ref> On September 6, 1847, he appointed [[Manlius V. Thomson]] as colonel, [[Thomas L. Crittenden]] as lieutenant colonel and Breckinridge as [[Major (United States)|major]] of the Third Kentucky Infantry Regiment.<ref name=heck21 /><ref name=davis34 /> The regiment left Kentucky on November 1 and reached [[Veracruz, Veracruz|Vera Cruz]] by November 21.<ref name=heck22>Heck, p. 22</ref> After several men became ill at Vera Cruz, the regiment hurried to [[Mexico City]].<ref name=heck22 /> Reports indicate that Breckinridge walked all but two days of the journey, allowing weary soldiers to use his horse.<ref name=heck22 /> When the Third Kentucky reached Mexico City on December 18, the fighting was almost over; they participated in no military action and remained in the city as an army of occupation until May 30, 1848.<ref name=heck22 /><ref name="Sifakis71">Sifakis, p. 71.</ref>
In demand more for his legal expertise than his military training, he was named as assistant counsel for [[Gideon Johnson Pillow]] during a court of inquiry initiated against him by [[Winfield Scott]].<ref name=davis37>Davis, p. 37</ref><ref name=heck23>Heck, p. 23</ref> Seeking to derail Scott's presidential ambitions, Pillow and his supporters composed and published letters that lauded Pillow, not Scott, for the American victories at [[Battle of Contreras|Contreras]] and [[Battle of Churubusco|Churubusco]].<ref name=davis38>Davis, p. 38</ref> To hide his involvement, Pillow convinced a subordinate to take credit for the letter he wrote.<ref name=davis38 /> Breckinridge biographer [[William C. Davis (historian)|William C. Davis]] writes, that it was "most unlikely" that Breckinridge knew the details of Pillow's intrigue.<ref name=davis38 /> His role in the proceedings was limited to questioning a few witnesses; records show that Pillow represented himself during the court's proceedings.<ref name=heck23 /><ref name=davis38 />
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