What If: The Union Loses at Gettysburg

Gettysburg is often described as the high-water mark of the Confederacy—the moment when Robert E. Lee’s Army of Northern Virginia reached its furthest advance into Union territory. Yet what if things had gone differently? What if Lee had spotted Union positions earlier, maneuvered more cautiously, or if key figures like Longstreet had been in command under different circumstances? Would it have changed the outcome? 

To explore this topic, let’s start with the most often cited blunder on the Confederate side—General J.E.B. Stuart’s cavalry. 

The Fog of War and Stuart’s Absence

Much of the Confederate misfortune at Gettysburg often focuses on a critical intelligence gap. General J.E.B. Stuart’s cavalry, normally Lee’s eyes and ears, was absent for a crucial week period. Without Stuart, Lee lacked accurate information about Union troop movements and positions. If the Confederates had conducted better reconnaissance, they might have identified the Union army in advance and seized high ground south of Gettysburg before the Federals could consolidate.

Map of troop movements and positions during the first day of the Battle of Gettysburg (July 1, 1863), showing Confederate forces in red and Union forces in blue as they engaged northwest and north of Gettysburg, Pennsylvania, ultimately pushing Union defenders back through the town toward Cemetery Hill.

However, the Union won the positional game after Day 1 of fighting, despite tactically losing by ceding the town itself. Recognizing the importance of the nearby highground, Union Commander Winfield Scott Hancock redeployed forces on Cemetery Hill, Cemetery Ridge, and Culp’s Hill, forming a strong “fishhook” line that allowed rapid reinforcement along interior lines. Even if Lee had massed his army perfectly, these defensive advantages made frontal assaults extraordinarily costly.

Lee’s Gamble and Strategic Flaws

Lee’s Pennsylvania invasion was bold but founded on a strategic miscalculation. He hoped that a major victory on Union soil would force Northern leaders to negotiate peace (I can’t help but think the Japanese did not learn this lesson with their daring attack on Pearl Harbor years later). In truth, Northern resolve was strong, bolstered by political, moral, and industrial advantages. A Confederate win at Gettysburg might have boosted Southern morale, but it would not have compelled the Union to surrender.

Lee’s decision to engage at Gettysburg rather than withdraw to more favorable terrain was influenced by overconfidence, limited intelligence, and the aggressive doctrine he had inherited from victories in Virginia. He gambled on his army’s skill, but without full information, he found himself fighting on Union terms: uphill, into fortified positions, and along interior lines the Federals controlled.

The Voices of Caution

Among Lee’s generals, there were dissenting voices. James Longstreet, commanding one of Lee’s corps, advocated for a more cautious, defensive approach. He urged Lee to flank the Union army or force it to attack Confederate positions, avoiding direct assaults on well-entrenched heights. Longstreet foresaw the deadly cost of frontal attacks and argued for maneuver over audacity.

Stonewall Jackson, had he survived Chancellorsville, might also have influenced Lee’s plans. Known for rapid flanking maneuvers and coordinated interior lines, Jackson’s presence could have changed Lee’s decision calculus. Without him, Lee lacked a commander capable of executing complex operational maneuvers under uncertainty.

What-If Scenarios: Could the Confederates Have Won?

Several counterfactual scenarios suggest a Confederate victory, while extremely difficult, was not entirely impossible:

1. Better Intelligence 

Timeline: June 26 – July 1, 1863

General Lee’s Gettysburg campaign was critically hampered by the prolonged absence of Major General J.E.B. Stuart’s cavalry, depriving the Army of Northern Virginia of timely and reliable intelligence on Union movements. Lee openly acknowledged this deficiency, writing, “I have no accurate information of the enemy’s movements.” 

That absence, however, has been the subject of considerable historical debate. While Stuart is often blamed for leaving Lee “blind,” several historians argue that Stuart was operating within the broad discretion granted by Lee’s orders. Lee’s instructions authorized Stuart to screen the army or ride around the Union flank if opportunities arose, without clearly defining priorities or contingencies. As historian Stephen Sears notes, “Stuart was not acting in defiance of orders so much as exploiting their ambiguity.” Compounding this issue, Lee failed to employ the three cavalry brigades remaining with the army aggressively enough to compensate for Stuart’s absence, a lapse that further degraded Confederate situational awareness.

What-If: Stuart with Clearer Orders

Had Stuart maintained continuous contact with Union movements, Lee might have gained early confirmation that the Army of the Potomac was concentrating rapidly along the road network leading to Gettysburg. This intelligence could‘ve revealed the Union’s occupation of Cemetery Hill and Cemetery Ridge before those positions were fully fortified.

Yet even this counterfactual has limits. Stuart’s ride around the Union army was delayed by unexpected encounters with Federal columns, and by the time his command reached Lee on July 2, his men and horses were badly worn. Historian Eric Wittenberg emphasizes that Stuart’s cavalry, even if it had arrived earlier, “was in no condition to conduct immediate, wide-ranging reconnaissance operations.” Thus, the mere presence of Stuart does not guarantee perfect intelligence.

With better information earlier in the campaign, Lee might still have retained greater operational flexibility. He could have maneuvered around Gettysburg to seize favorable high ground south or east of the town, forcing the Union army to respond. Alternatively, Lee might have struck an isolated Union corps before full concentration. 

However, Union intentions complicate this scenario. General George G. Meade initially planned to fight a defensive battle along Pipe Creek in Maryland, in a stronger, better-prepared position. Had Lee known the Union was moving rapidly toward Gettysburg, he might still have advanced there, only for Meade to disengage and fall back to Pipe Creek, potentially producing a major battle elsewhere under similarly unfavorable conditions for the Confederates.

Impact: Avoiding an Unplanned Battle 

Superior reconnaissance alone would not have guaranteed Confederate success, but it could have prevented the Army of Northern Virginia from stumbling into a major engagement under suboptimal conditions. The absence of clear intelligence constrained Lee’s decision-making, contributed to the unplanned collision at Gettysburg, and ultimately led to costly assaults against strong defensive positions on July 2–3. At minimum, better intelligence might have preserved Confederate combat power and allowed Lee to dictate when and where he fought—if not the final outcome itself.

2. Choosing the Battlefield

Timeline: June 30 – July 1, 1863

A central assumption in many counterfactuals of Gettysburg is that Robert E. Lee retained the freedom to maneuver and deliberately choose a battlefield favorable to the Army of Northern Virginia. Strategically, Lee’s objectives in the Pennsylvania Campaign support this premise—to a point. Lee did not intend to permanently occupy Northern territory. Rather, his invasion aimed to win a decisive battle on Union soil, undermine Northern morale, threaten major cities such as Harrisburg or Philadelphia, and potentially force the Lincoln administration to negotiate or redeploy forces from other theaters. 

However, the feasibility of battlefield selection was constrained by operational realities. The Battle of Gettysburg began not as a planned engagement, but as a chance encounter on July 1, when Confederate infantry entered Gettysburg in search of supplies and unexpectedly collided with Union cavalry under Brig. Gen. John Buford. Once significant forces became engaged, disengaging an entire army in the presence of an enemy of equal strength, particularly without reliable cavalry intelligence, was both a dangerous and difficult proposition. 

What-If: Lee Has More Freedom to Manuever 

In theory, Lee might have avoided immediate engagement and maneuvered south or east toward Hanover or York, compelling the Union army to stretch its lines or attack Confederate-held high ground. Such an approach echoed Lee’s preference for maneuver warfare and forcing the enemy to attack, most notably demonstrated at Chancellorsville.

Yet this comparison has limits. Unlike Joseph Hooker, Union commander George G. Meade anticipated Confederate maneuver and adopted a fundamentally defensive posture. Meade had already identified the Pipe Creek Line in Maryland as a favorable defensive position and, once engaged at Gettysburg, rapidly formed a strong defensive alignment along Cemetery Hill and Cemetery Ridge. Any major Confederate flanking movement toward Hanover or York would likely have been detected by Union cavalry and signal stations, enabling Meade to counter or disengage on his own terms.

Map showing military positions and engagements on the second day of the Battle of Gettysburg (July 2, 1863), with Confederate and Union forces arrayed across key terrain such as Little Round Top, Devil’s Den, the Wheatfield, Cemetery Ridge, and Culp’s Hill—reflecting the intense, multi‑sector fighting as Lee’s army probed the Union “fishhook” defensive line.

Moreover, the notion that Confederate forces might have secured interior lines runs counter to the battlefield’s eventual geometry. It was the Union army that occupied the dominant terrain and interior lines, allowing Meade to reinforce threatened sectors rapidly on July 2 and July 3—precisely the advantage the Confederates lacked.

Lee’s decision-making was further complicated by incomplete intelligence. Emboldened by prior victories and deprived of effective cavalry reconnaissance during the campaign’s critical opening days, Lee appears to have underestimated both the speed with which the Army of the Potomac concentrated and the strength of its defensive positions.

Impact: Fight or Run 

While the hypothetical benefits of maneuver, forcing the Union to attack, selecting favorable terrain, and engaging piecemeal, are sound military principles, the practical realities of Gettysburg made their execution unlikely. Logistical strain, limited intelligence, and Meade’s rapid and effective response narrowed Lee’s options. By July 1, Lee faced a stark choice: accept battle where the armies met or withdraw toward Virginia, forfeiting the campaign’s strategic momentum—an option he was reluctant to embrace.

3. Longstreet in Command 

Timeline: July 1–3, 1863

Lieutenant General James Longstreet has long been characterized as Lee’s most cautious senior subordinate, and this assessment is broadly supported by both wartime evidence and modern scholarship. Longstreet consistently advocated a tactical defensive strategy, arguing that the Confederacy’s limited manpower required forcing the Union army to attack well-prepared positions rather than expending Confederate strength in frontal assaults. His views were shaped by battlefield experience and validated by Confederate successes at Fredericksburg and later at Chickamauga, where defensive positioning and terrain exploitation proved decisive.

Longstreet’s disagreement with Lee at Gettysburg—particularly regarding the July 3 assault known as Pickett’s Charge—is well documented. In his postwar memoir, From Manassas to Appomattox, Longstreet described the proposed attack against fortified Union heights as a “murderous” mistake and argued instead for maneuvering around the Union left to compel Meade to attack on Confederate-chosen ground. While Longstreet’s memoirs must be read critically due to their apologetic tone amid postwar controversy, his opposition to frontal assaults is corroborated by contemporaneous correspondence and the accounts of other Confederate officers.

What-If: Lee Is Wounded and Cannot Command 

Had Lee been wounded or incapacitated during the fighting on July 1 or July 2, Longstreet—as the army’s senior corps commander—would almost certainly have assumed operational control. Based on his documented tactical philosophy and his explicit objections at Gettysburg, it is highly plausible that Longstreet would have rejected a massed frontal assault like Pickett’s Charge on July 3.

Map of troop positions and movements during the third day of the Battle of Gettysburg (July 3, 1863), illustrating the Union defensive line anchored along Cemetery Ridge and Seminary Ridge, the massed Confederate artillery positions, and the route of the infantry assault known as Pickett’s Charge—the climactic attack that failed to break the Union center and marked the effective end of Lee’s offensive.

Instead, Longstreet likely would have pursued a more conservative, maneuver-based approach. This could have included strengthening defensive positions, employing artillery to apply sustained pressure on Union lines, and conducting limited probing or flanking operations rather than committing to a decisive head-on attack. Such methods were consistent with Longstreet’s preference for leveraging terrain, conserving manpower, and forcing the enemy to bear the burden of assault—an approach that reflected both Confederate strategic necessity and Longstreet’s personal battlefield philosophy. 

Despite its plausibility, this scenario remains hypothetical. The actual command structure left Lee firmly in control, and Longstreet ultimately executed orders he opposed. Moreover, even under Longstreet’s leadership, significant constraints would have persisted: the Union army held commanding terrain with interior lines, Confederate logistics were strained, and cavalry intelligence remained limited. These factors would have restricted the scope of any maneuver and may still have compelled a withdrawal or stalemate rather than victory.

Impact: Army of Northern Virginia Stays More Intact 

A Longstreet-led Army of Northern Virginia would not necessarily have won the Battle of Gettysburg. However, it likely would have avoided the catastrophic losses of July 3. By declining a massed frontal assault and emphasizing defensive and maneuver-oriented tactics, Longstreet might have preserved Confederate combat power for continued operations. In retrospect, many historians argue that Longstreet’s strategic instincts were sound—and that his postwar reputation suffered largely because his criticisms of Lee conflicted with the emerging “Lost Cause” narrative, which elevated audacity over prudence and punished dissent from Lee’s decisions.

4. Avoiding Frontal Assaults

Timeline: July 2–3, 1863

The Confederate failures on July 2 and July 3 stemmed largely from repeated direct assaults against well-fortified Union positions. By the second day of battle, the Army of the Potomac occupied strong defensive ground along Cemetery Ridge and Culp’s Hill, protected by breastworks and supported by interior lines. Confederate attacks—most notably Pickett’s Charge on July 3 and Ewell’s assaults on Culp’s Hill on July 2–3—were frontal in nature and inflicted catastrophic losses without breaking the Union line.

These assaults proved extraordinarily costly. Many Confederate units suffered casualty rates exceeding 50 percent, losses the Army of Northern Virginia could not replace. By contrast, Union forces could absorb casualties and continue reinforcing their defensive positions, shifting the strategic balance decisively against Lee.

What-If: Better Confederate Coordination 

While the Union center was strongest, its flanks—Culp’s Hill on the right and Little Round Top on the left—were comparatively more vulnerable. On the evening of July 2, Confederate forces under Brig. Gen. George H. Steuart actually reached Union breastworks on Culp’s Hill and came perilously close to the Baltimore Pike, the Union army’s primary supply and communication route. Had this position fallen, it would have posed a serious operational crisis for Meade.

However, Ewell’s attacks were poorly coordinated and commenced late in the day, allowing Meade to shift reinforcements efficiently. Some historians argue that a more deliberate, corps-level assault at dawn on July 2—before Union entrenchments were fully strengthened and before reinforcements arrived—might have had a greater chance of success. Even so, the terrain was rugged, communication was difficult, and success was far from guaranteed. 

Illustration of General Pickett’s famous charge at the Battle of Gettysburg, from the 1903 history compilation Makers of the World’s History and Their Grand Achievements (engraving after Alfred Waud by Alfred Swinton), showing Confederate troops advancing toward Union lines on July 3, 1863.

Lee frequently employed probing attacks to test enemy lines, but at Gettysburg, Confederate timing and coordination consistently fell short. Rather than massing forces for a single, slow-moving, and highly visible assault like Pickett’s Charge, sustained, smaller-scale attacks along multiple sectors might have limited Meade’s ability to shift troops rapidly along his “fishhook” defensive line.

In practice, Confederate command-and-control problems—poor staff work, inadequate reconnaissance, and delayed communications—made true simultaneity difficult. The Union army, by contrast, demonstrated exceptional flexibility in reinforcing threatened points.

Given Confederate numerical inferiority and the South’s limited manpower reserves, conserving combat strength was strategically essential. The July 2–3 assaults were widely described by contemporaries as “bloody affairs” that left the Army of Northern Virginia incapable of sustained offensive action afterward. A less aggressive posture on July 3 might not have produced victory, but it could have preserved sufficient strength to conduct a fighting withdrawal or hold defensively rather than retreat under pressure.

Impact: The Union Gives Up Ground 

Had Culp’s Hill fallen on the evening of July 2—or had coordinated pressure forced the Union right to give ground—Meade might have been compelled to disengage and fall back to the Pipe Creek Line, his preselected defensive position in Maryland. However, this outcome remains speculative. Union troops were well entrenched, increasingly reinforced, and operating on interior lines that favored rapid concentration against threats.

This counterfactual correctly identifies the Confederate army’s principal tactical failures at Gettysburg: poor coordination, inadequate exploitation of temporary weaknesses, and an overreliance on brute-force frontal assaults. Where it risks overstatement is in underestimating the difficulty of maneuvering in Gettysburg’s terrain and the effectiveness of Meade’s defensive system. The strategy described was militarily sounder than what was attempted, but its success was far from assured, given the Union’s strong defensive posture and Confederate command limitations.

Limitations and Realities

Even if all these adjustments occurred, Union advantages remained formidable. Gettysburg was stacked against the Confederates before the first shot. Yet these scenarios illustrate that better intelligence, maneuver, and cautious command could have dramatically altered the battle, potentially turning a decisive Union victory into a less decisive one, a costly stalemate—or, in a narrow set of circumstances, a Confederate success that cannot be properly exploited to achieve ultimate victory.

Sources

1. Coddington, E. B. (1968). The Gettysburg campaign: A study in command. New York, NY: Scribner.

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13. Wittenberg, E. J. (2008). Plenty of blame to go around: Jeb Stuart’s controversial ride to Gettysburg. New York, NY: Savas Beatie.

Images

1. Commons Wikimedia. (n.d.). Battle of Gettysburg [L. Prang & Co. lithograph print of Thure de Thulstrup painting, restored by Adam Cuerden] [Image]. Wikimedia Commons. https://commons.wikimedia.org/wiki/File:Thure_de_Thulstrup_-_L._Prang_and_Co._-_Battle_of_Gettysburg_-_Restoration_by_Adam_Cuerden.jpg

2. Commons Wikimedia. (n.d.). Gettysburg battle map day 1 [Map]. Wikimedia Commons. https://commons.wikimedia.org/wiki/File:Gettysburg_Battle_Map_Day1.jpg

3. Commons Wikimedia. (n.d.). Gettysburg battle map day 2 [Map]. Wikimedia Commons. https://commons.wikimedia.org/wiki/File:Gettysburg_Battle_Map_Day2.jpg

4. Commons Wikimedia. (n.d.). Gettysburg battle map day 3 [Map]. Wikimedia Commons. https://commons.wikimedia.org/wiki/File:Gettysburg_Battle_Map_Day3.jpg

5. Commons Wikimedia. (n.d.). Makers of the world's history and their grand achievements (1903) [Illustration of Pickett’s Charge]. Wikimedia Commons. https://commons.wikimedia.org/wiki/File:Makers_of_the_world%27s_history_and_their_grand_achievements_(1903)_(14596104027).jpg