Commonwealth of Kentucky v. Telly Savalas Denson, 529 S.W.3d 739

In April 2016 Kentucky amended KRS 189A.010 to expand the DUI prior-offense "look-back" period from five years to ten years, effective immediately.
Joshua Jackson and Telly Denson were charged with DUI (Fourth Offense) for conduct after the amendment; each had a prior DUI conviction older than five years but within ten years (Jackson: plea in 2009; Denson: plea in 2011).
Their prior convictions were entered pursuant to written plea agreements that described the then-applicable five-year penalty ranges but did not expressly promise that those convictions could never be used to enhance future penalties beyond five years.
The Warren Circuit Court ruled sua sponte that the plea agreements created contractual promises insulating the defendants from enhancement based on prior DUIs older than five years, and excluded the 2009 and 2011 convictions.
The Commonwealth appealed; the Kentucky Supreme Court accepted transfer and reversed the trial court, holding the plea agreements did not bar application of the new ten-year look-back period.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether plea agreements created a contract-based promise that prior DUIs could only enhance future penalties for five years	Commonwealth: plea agreements are contracts but here they did not promise a permanent five-year limitation	Jackson/Denson: plea language describing five-year ranges reasonably implied protection from enhancements after five years	Reversed: boilerplate penalty ranges do not reasonably promise immunity from future legislative changes; no contractual bar to using priors within ten years
Whether applying the 2016 amendment violates ex post facto or KRS 446.080(3) retroactivity rules	Commonwealth: amendment was in effect when current offenses occurred, so no ex post facto or retroactivity problem	Defendants: increasing look-back period penalizes them based on older convictions and is retroactive/punitive	Held: No ex post facto violation; amendments apply because current crimes occurred after effective date; not retroactive application
Whether Boykin due-process requirements invalidate pleas because defendants did not know of future legislative changes	Commonwealth: unforeseeable future legislative changes do not implicate Boykin rights	Defendants: pleas were made without awareness that consequences could later increase enhancement exposure	Held: Boykin does not require warning of unforeseeable future legislative changes; pleas remain valid

McClanahan v. Commonwealth, 308 S.W.3d 694 (Ky. 2010) (plea agreements interpreted under ordinary contract principles)
Buck v. Commonwealth, 308 S.W.3d 661 (Ky. 2010) (ex post facto analysis for criminal statutes)
Pate v. Department of Corrections, 466 S.W.3d 480 (Ky. 2015) (ex post facto inquiry considers whether law imposes additional punishment)
Commonwealth v. Ball, 691 S.W.2d 207 (Ky. 1985) (applying new DUI penalty provisions to subsequent offenses committed after enactment)
Smith v. Commonwealth, 400 S.W.3d 742 (Ky. 2013) (plea agreements and contract-law principles)
Kentucky Shakespeare Festival, Inc. v. Dunaway, 490 S.W.3d 691 (Ky. 2016) (contract interpretation is a question of law reviewed de novo)
Elmore v. Commonwealth, 236 S.W.3d 623 (Ky. App. 2007) (once plea is accepted, the accused is entitled to the benefit of the bargain)