SUPREME COURT OF MISSOURI 

en banc 

BRIAN NAIL, ) 

 ) 

Appellant, ) 

 ) 

v. ) No. SC93543 

 ) 

HUSCH BLACKWELL SANDERS, LLP, ) 

 ) 

Respondent. ) 

 )

APPEAL FROM THE CIRCUIT COURT OF JACKSON COUNTY 

The Honorable Sandra C. Midkiff, Judge 

Opinion issued June 24, 2014 

Introduction 

 Brian Nail appeals from the trial court’s entry of judgment in favor of Husch 

Blackwell Sanders, LLP1

 in a legal malpractice action. Prior to this case, Husch 

Blackwell represented Nail in a dispute with his former employer over his stock options. 

Nail had options to purchase the employer’s stock within 18 months after the termination 

of his employment, but, when his former employer merged with another company, the 

stock was “locked up” for 12 months after the merger. The value of the stock declined 

significantly during the lockup period. Husch Blackwell eventually negotiated a 

 

1

 This firm is now known as “Husch Blackwell LLP.” 

1 
2 

settlement that extended Nail’s option period, but when Nail attempted to exercise his 

options under the settlement agreement, complications arose that prevented him from 

immediately obtaining the stock. 

 Nail later sued Husch Blackwell for legal malpractice, alleging that Husch 

Blackwell (1) negligently advised him regarding his remedies in the dispute with his 

employer; and (2) negligently drafted the settlement agreement. He sought to recover the 

highest value of the stock during the lock-up period, or, alternatively, the amount of the 

settlement agreement’s liquidated damages clause. The record does not show, however, 

that the decline in the value of Nail’s stock options was a reasonable or probable result of 

Husch Blackwell’s allegedly deficient advice. Nor does it show that Nail’s employer 

would have agreed to include provisions in the settlement agreement that would have 

allowed Nail to receive liquidated damages, and there was no evidence that the employer 

would have then breached any such provisions. Accordingly, the trial court’s judgment is 

affirmed because Nail failed to prove that Husch Blackwell’s alleged negligence caused 

his claimed damages. 

Factual and Procedural Background 

 As the chief financial officer of MTW Corporation, Nail acquired options to 

purchase stock in the company from its owner, Richard Mueller. When his employment 

was terminated in March 2001, he negotiated a separation agreement that permitted him 

to exercise his stock options until September 2002. The separation agreement provided 

that if MTW merged with another corporation, Nail’s stock options would be converted 

into options to purchase stock in the successor company. 
In July 2001, MTW was acquired in a stock-for-stock merger by The Innovation 

Group (“TIG”), a United Kingdom corporation with stock traded on the London Stock 

Exchange. The merger converted Nail’s options to purchase MTW stock into options to 

purchase shares of TIG stock. As a condition of the merger, Mueller agreed to “lock up” 

his shares of TIG stock for one year, during which time he could not sell or transfer TIG 

stock without board approval. This included the stock to which Nail held options. 

 Nail learned of the MTW-TIG merger shortly before it became final, and he 

retained Husch Blackwell2

 for advice on how to protect his stock option rights. Husch 

Blackwell first asked TIG’s board of directors to approve Nail’s exercise of his stock 

options, but it refused. Nail and his attorneys then had several discussions regarding his 

possible courses of action. Nail knew he always had the option to sue. According to 

Nail, however, Husch Blackwell consistently advised him that litigation was unlikely to 

be successful, and he should attempt to settle with Mueller. 

 In March 2002, on Husch Blackwell’s advice, Nail attempted to exercise some of 

his stock options. Mueller refused to transfer the stock, and Husch Blackwell threatened 

litigation. Shortly thereafter Nail and Mueller entered into a settlement agreement under 

which Mueller agreed to extend the option period by five years, place the shares Nail had 

options to purchase in an escrow account, and give Nail a $50,000 credit toward the 

exercise of his options. In return, Nail released Mueller from liability for breach of the 

separation agreement. Under the settlement agreement, Mueller was required to deliver a 

 

2

 For convenience, this opinion refers to Husch Blackwell and the attorneys involved in this case 

collectively as “Husch Blackwell.” Husch Blackwell does not dispute its liability for the actions 

of the attorneys who represented Nail. 

3 
transfer notice at the expiration of the lock-up period, which would place the shares of 

TIG stock Nail had options to purchase in escrow. Once the transfer notice was 

delivered, Nail would be free to exercise his stock options. To ensure Mueller’s 

compliance, the settlement agreement included a liquidated damages clause, which 

provided that Mueller’s failure to timely deliver the transfer notice would result in 

damages equal to the highest value of TIG stock during the remainder of the lock-up 

period without regard to the cost of exercising the options. The settlement agreement 

also required Mueller to execute and deliver any other documents necessary to transfer 

the stock. 

 Meanwhile, the price of TIG stock rose following the merger and then declined. 

From a price of about 2.9 Pounds per share (roughly $4) at the beginning of the lock-up 

period in July 2001, the stock price rose above 4 Pounds (more than $6) in August 2001. 

The stock price rapidly declined in October 2001, falling below 2 Pounds (less than $3). 

It rebounded in November and December 2001, approaching 4 Pounds per share (about 

$5), but in February 2002 it began a steady decline. In March 2002, when Nail and 

Mueller entered the settlement agreement, the stock was trading at 2.4 Pounds per share 

(about $3.50), and when the lock-up period expired in July 2002, the stock price had 

fallen below 1 Pound (approximately $1). The price remained low during Nail’s 

extended exercise period and never rose above above 1 Pound before the period expired.3

 

3

 Nail and Husch Blackwell disagree on the precise value of TIG stock on each of the dates in 

question. The record is reviewed in the light most favorable to the party against whom summary 

judgment was entered. ITT Commercial Fin. Corp. v. Mid-Am. Marine Supply Corp., 854 

S.W.2d 371, 381 (Mo. banc 1993). Accordingly, the values set forth above are those provided 

4 
When the lock-up period ended, Mueller timely delivered the transfer notice, and 

Nail used his $50,000 credit to purchase TIG shares. To complete transfer of the stock, 

however, the London Stock Exchange required Mueller to deliver a stock transfer form, 

and Nail was required to pay a stamp duty. Mueller promptly delivered the necessary 

form, but Nail objected to the $285 stamp duty and refused to pay it. The stock was not 

registered in Nail’s name until he paid the stamp duty nearly two years later.4

 Nail later sued Husch Blackwell. He alleged that the law firm was negligent in 

two respects. First, he argued that Husch Blackwell negligently advised him regarding 

his remedies for Mueller’s interference with his stock option rights because it failed to 

advise him to tender an exercise of his options immediately following the MTW-TIG 

merger. According to Nail, this failure caused damages equal to the difference between 

the highest value of the stock during the lock-up period and what it would have cost him 

to acquire the stock, which amounted to several million dollars.5

 Second, Nail argued 

that Husch Blackwell negligently drafted the settlement agreement by failing to require 

Mueller to place all of the documents necessary to transfer the stock in escrow at the end 

 

by Nail. The parties generally agree, however, that the price of TIG stock initially increased 

during the lock-up period, reaching its zenith in August 2001, and then fell below its pre-lock-up 

period value for the remainder of the lock-up period and Nail’s extended exercise period. 

4

 Nail later retained different counsel and sued Mueller. He initially sought either: (1) to set 

aside the settlement agreement and obtain damages for breach of the separation agreement; or (2) 

to obtain damages under the settlement agreement’s liquidated damages clause because the 

transfer notice was ineffective. He ultimately abandoned his first claim, and his second claim 

failed, largely because Mueller promptly provided the additional documents required by the 

London Stock Exchange. Nail and Mueller reached a second settlement giving Nail another 

$50,000 credit toward the exercise of his options. 

5

 Nail claims damages in excess of $17 million. This figure is based on a peak stock value of 

more than $6, plus interest. Nail had options to purchase more than 2.1 million shares of TIG 

stock: approximately 1.85 million shares at $.3129 per share, and about 265,000 shares at $1.43 

per share, for a total cost of just under $1 million. 

5 
of the lock-up period. Nail claimed that this failure caused him to lose a liquidated 

damages claim against Mueller worth millions of dollars.6

 Husch Blackwell moved for summary judgment. The trial court initially granted 

summary judgment on Nail’s first claim, holding that Nail failed to prove that Husch 

Blackwell’s alleged negligence caused the harm for which he sought to recover.7

 It also 

granted partial summary judgment on Nail’s second claim, finding that Husch Blackwell 

was not liable for the amount of the liquidated damages clause, but it denied summary 

judgment to the extent that Nail could prove he was damaged when his exercise of stock 

options was delayed until Mueller submitted the stock transfer form. After Nail 

stipulated that he suffered no harm during this time period, the trial court entered a 

judgment for Husch Blackwell. This appeal follows.8

Standard of Review 

 Summary judgment is proper when no genuine issue of material fact exists and the 

movant is entitled to judgment as a matter of law. Rule 74.04. A “defending party” may 

establish a right to summary judgment by showing (1) facts that negate any of the 

claimant’s necessary elements; (2) that the claimant, after an adequate period of 

 

6

 The settlement agreement’s liquidated damages clause provided for damages in an amount 

equal to the highest value of the stock during the remainder of the lock-up period. According to 

Nail, the highest value for TIG stock during this time was 2.45 Pounds, or approximately $3.48 

per share. Multiplied by the 2.1 million shares on which Nail held options, this would have 

yielded more than $7 million in liquidated damages. 

7

 The trial court also held that summary judgment was appropriate because Nail had waived this 

claim when he abandoned his breach of contract claim against Mueller in the earlier litigation. 

Because summary judgment is appropriate on the issue of causation, the waiver argument need 

not be addressed. 

8

 This Court granted transfer after an opinion by the court of appeals. Mo. Const. art. V, sec. 10. 

6 
discovery, has not been able and will not be able to produce sufficient evidence to allow 

the trier of fact to find the existence of any one of the claimant’s elements; or (3) that 

there is no genuine dispute as to the existence of the facts required to support the 

movant’s properly pleaded affirmative defense. ITT Commercial Fin. Corp. v. Mid-Am. 

Marine Supply Corp., 854 S.W.2d 371, 381 (Mo. banc 1993). Because the propriety of 

summary judgment is an issue of law, review is essentially de novo, and the trial court’s 

judgment may be affirmed on any basis supported by the record. Id. at 376, 387-88. 

Analysis 

 Nail asserts two legal malpractice claims against Husch Blackwell. In his first 

claim, he argues that Husch Blackwell negligently advised him regarding his remedies 

for Mueller’s interference with his stock option rights, and that this negligence caused 

damages equal to the difference between the highest value of the stock during the lock-up 

period and his cost to acquire the stock. In his second claim, Nail argues that Husch 

Blackwell negligently drafted the settlement agreement, and that, but for its negligence, 

he would have had a liquidated damages claim against Mueller. 

 Both claims require Nail to prove “(1) that an attorney-client relationship existed; 

(2) that defendant acted negligently or in breach of contract; (3) that such acts were the 

proximate cause of the plaintiff[’s] damages; [and] (4) that but for defendant’s conduct 

the plaintiff[] would have been successful in prosecution of their underlying claim.” 

Donahue v. Shugart, Thomson & Kilroy, P.C., 900 S.W.2d 624, 626 (Mo. banc 1995). 

Because each claim is grounded in separate facts, they will be examined in turn. 

7 
Negligent Advice Claim 

 Nail first contends that Husch Blackwell negligently advised him of his remedies 

after Mueller agreed to lock up his stock in the wake of the MTW-TIG merger. 

According to Nail, he informed Husch Blackwell that the sole purpose of its 

representation of him was to protect his stock option rights, and they had several 

discussions regarding his possible courses of action. Husch Blackwell did not, however, 

advise him of the need to exercise his stock options until March 2002, long after the 

merger. Nail’s expert, John Tollefsen, opined that a reasonable attorney would have 

advised Nail to exercise his stock options immediately after the merger, and Husch 

Blackwell’s failure to do so was negligent. Tollefsen reasoned that Nail should have 

been advised to exercise his stock options immediately because: (1) he had to exercise 

them to establish Mueller’s breach of the separation agreement; and (2) exercising the 

stock options would fix his damages at the difference between what he could have sold 

the stock for on the date he exercised his options and his cost to acquire the stock. In 

addition, according to Tollefsen, exercising his options as early as possible was risk-free: 

exercise would create a breach, fix damages at the time of exercise, and if the share price 

went up, Nail could recover the gain in a claim for unjust enrichment.9

 Husch Blackwell disputes Nail’s allegations of negligence. The litigation in this 

case, however, has focused on the issue of causation. Like all negligence actions, legal 

 

9

 The trial court did not decide the merits of the legal arguments embedded in Tollefsen’s 

opinion, and the parties have not briefed these issues. This Court expresses no opinion as to the 

merits of these arguments. 

8 
malpractice requires proof of causation. Zafft v. Eli Lilly & Co., 676 S.W.2d 241, 244 

(Mo. banc 1984). Proof of causation entails proof of causation in fact, or “but-for” 

causation, as well as proximate causation. Callahan v. Cardinal Glennon Hosp., 863 

S.W.2d 852, 862, 865 (Mo. banc 1993). In legal malpractice cases, causation in fact 

requires proof that, “but for” the attorney’s negligence, the result would have been 

different. Donahue, 900 S.W.2d at 626. This is often called proving a “case within a 

case” or a “trial within a trial.” 4 R.E. MALLEN & J.M. SMITH, LEGAL MALPRACTICE 

§ 37:25, at 1708-09 (2014 ed.); RESTATEMENT (THIRD) OF LAW GOVERNING LAWYERS 

§ 53 cmt. b (2000). The plaintiff must also prove proximate causation, or that the injury 

was a reasonable and probable consequence of the defendant’s negligence. Donahue, 

900 S.W.2d at 626; Callahan, 863 S.W.2d at 865. 

 In legal malpractice cases, causation in fact and proximate causation are often both 

subsumed within the “case within a case.” By proving that the result of the underlying 

proceeding would have been different “but for” the attorney’s negligence, the plaintiff 

also proves that the damages—the difference between what the result would have been

and what it was—were the reasonable and probable consequence of the defendant’s 

negligence. 

 Nail’s claim, however, is a novel one. Nail argues that Husch Blackwell was 

negligent in failing to advise him to exercise his stock options immediately after the 

MTW-TIG merger. He claims to have suffered damages equal to the highest value of the 

stock during the lock-up period minus the cost of exercising his options. The connection 

between the alleged negligence and the claimed harm is attenuated. Mueller, not Husch 

9 
Blackwell, prevented Nail from exercising his stock options during the lock-up period. 

To connect Husch Blackwell’s alleged negligence to his claimed harm, Nail argues that, 

if he had exercised his stock options immediately after the MTW-TIG merger, he would 

have established a breach of contract claim against Mueller that would have allowed him 

to recover based on the highest value of the stock during the lock-up period. He further 

hypothesizes that he would have realized the value of that claim by either prevailing in a 

breach of contract lawsuit against Mueller or settling with him. 

 Assuming that this theory would satisfy the “but-for” test for causation in fact, it is 

nevertheless insufficient to establish proximate causation. Proximate cause requires more 

than mere causation in fact because “the ‘but for’ test serves only to exclude items that 

are not causal in fact; it will include items that are causal in fact but that would be 

unreasonable to base liability upon because they are too far removed from the ultimate 

injury or damage.” Callahan, 863 S.W.2d at 865. The general test for proximate cause is 

whether the claimed injury is the natural and probable consequence of the defendant’s 

alleged negligence. Id. Proximate cause inquires into the scope of foreseeable risk 

created by the defendant’s act or omission. Alcorn v. Union Pac. R.R. Co., 50 S.W.3d 

226, 239 (Mo. banc 2001), overruled on other grounds by Badahman v. Catering 

St. Louis, 395 S.W.3d 29 (Mo. banc 2013). The causal connection cannot be based on 

speculation or conjecture. Stanley v. City of Independence, 995 S.W.2d 485, 488 (Mo. 

banc 1999). Each case must be decided on its own facts. Krause v. U.S. Truck Co., Inc., 

787 S.W.2d 708, 710 (Mo. banc 1990). 

10 
Although Nail casts his damages claim as compensation for the amount he would 

have recovered in a breach of contract lawsuit, a careful parsing of his claim 

demonstrates that, in reality, Nail seeks to recover for the decline in the value of his stock 

options during the lock-up period. Nail’s theory of negligence is that Husch Blackwell 

failed to advise him of the legal consequences of exercising his stock options. Yet, in 

reality, Husch Blackwell did precisely what Nail claims it should have done. In March 

2002, Husch Blackwell advised Nail to partially exercise his stock options as a 

preliminary to settlement negotiations. The difference, of course, is that Husch 

Blackwell advised Nail to exercise his options in March 2002 rather than July 2001. But 

the delay itself did not impair Nail’s stock option rights. It did not prevent him from 

exercising his stock options, nor did it directly affect his remedies. The lock-up period 

imposed by Mueller prevented Nail from exercising his stock options, and even with the 

delay Nail was still able to establish facts to support a breach of contract claim against 

Mueller, which he ultimately settled for an extension of his stock option rights. 

 What changed between July 2001 and March 2002 was the price of TIG stock, 

and, therefore, the value of Nail’s stock options. But the decline in the stock price was 

caused by the vicissitudes of the market, not Husch Blackwell’s alleged negligence. 

Even if Husch Blackwell negligently advised Nail, it could not affect the market 

conditions that caused the stock’s value to decline any more than it could predict them. 

A decline in the stock price is outside the scope of harms that would naturally, probably, 

and foreseeably result from Husch Blackwell’s alleged negligence, and the causal 

11 
relationship between that negligence and TIG’s stock price is not even conjectural—it is 

nonexistent. 

 This conclusion is supported by the decisions of other courts that have considered 

whether the client in a professional malpractice suit can recover for losses caused by the 

market. The holdings in Movitz v. First National Bank of Chicago, 148 F.3d 760 (7th 

Cir. 1998); First Federal Savings & Loan Ass’n v. Charter Appraisal, 724 A.2d 497 

(1999); and Oregon Steel Mills v. Coopers & Lybrand, LLP, 83 P.3d 322 (Or. 2004), are 

instructive. 

 In Movitz, the plaintiff had invested in commercial real estate in Houston based 

partly on the defendant bank’s negligent evaluation of the property. When the Houston 

real estate market collapsed, the property went into foreclosure and sold for just over half 

the purchase price. The plaintiff lost its entire investment, and it sued the bank to recover 

for its loss. The court held that even though the plaintiff might not have invested in the 

property but for the bank’s negligence, the bank was not liable for its loss because the 

market collapse wiped out the investment. As the court noted, “The care that the bank 

was contractually required to take in advising [plaintiff] with regard to the purchase of 

the office building was not intended to prophesy or avert market fluctuations but to make 

sure that the building was a sound purchase under current market conditions.” Movitz, 

148 F.3d at 763. The court suggested that the bank might have been liable for losses 

caused by its negligence—for example, for the cost of correcting structural deficiencies 

the bank negligently failed to discover—but the extent of the market collapse far 

exceeded the amount of the plaintiff’s investment. 

12 
 Similarly, in Charter Appraisal, the plaintiff made a loan secured by real property 

after the defendant appraiser negligently overvalued the property. The borrower later 

defaulted, and the plaintiff foreclosed. By that time, real estate values in the area had 

declined by more than 25 percent, and the plaintiff was left with a large deficiency 

judgment. It sued the appraiser seeking to recover damages for its loss. The court 

allowed the plaintiff to recover damages for the portion of the deficiency that represented 

the difference between the property’s appraised value and its actual value at the time of 

the loan was made. It excluded from the damages award, however, the portion of the 

deficiency attributable to the market decline because “a fall in market values was not 

within the scope of risk created by the negligently conducted appraisal.” Charter 

Appraisal, 724 A.2d at 607. 

 In Oregon Steel Mills, the plaintiff, a steel company, was delayed in making a 

stock offering when its accounting firm discovered that it had negligently approved the 

company’s financial statements for a previous year. The accounting firm refused to 

approve an audit of the company’s financial statements until the error was corrected, 

which delayed the offering by about a month. In the meantime, market conditions 

depressed the price of stock in steel companies, including the plaintiff’s stock, and the 

plaintiff’s stock ultimately sold for less than it would have if the sale had not been 

delayed. The company sued the accounting firm for the loss caused by changes in the 

market price, but the court held that these losses were not recoverable because they were 

not a foreseeable consequence of the firm’s negligence. The court noted that it was 

foreseeable that an accounting firm’s negligence could affect its client’s stock price, but 

13 
the damages plaintiff sought were “based solely on the decline in the price of plaintiff’s 

stock” even though “the price decline affected all steel stocks and was unrelated to 

defendant’s misconduct.” Oregon Steel Mills, 83 P.3d at 344. 

 Nail’s claim is analogous to the claims in Movitz, Charter Appraisal, and Oregon 

Steel Mills. In each case, the plaintiff had something of value—in Nail’s case, it was a 

right to purchase certain shares of stock at a certain price—but its value depended almost 

entirely on the market. And in each case, the harm to the plaintiff’s value came from the 

market, not from the defendant’s negligence. This is not to say that an attorney’s 

negligence may never be the proximate cause of a decline in his or her client’s stock 

price. But like Movitz and Oregon Steel Mills, no part of Nail’s claimed damages 

represents losses caused by Husch Blackwell’s negligence. He seeks to recover solely for 

the decline in the stock’s value, which was caused entirely by the market. As a matter of 

law, the risk of a decline in Nail’s stock price was not a reasonable or probable 

consequence of Husch Blackwell’s alleged negligence. Accordingly, the trial court 

properly granted summary judgment on Nail’s negligent advice claim. 

Negligent Drafting Claim 

 Nail’s claim that Husch Blackwell negligently drafted the settlement agreement 

also fails for lack of causation. This time, however, he fails to make the threshold 

showing of causation in fact. In a nutshell, Nail’s theory of negligence is that the 

settlement agreement should have required Mueller to place all of the documents 

necessary to transfer the stock into escrow upon the expiration of the lock-up period; that 

14 
it did not; and this failure was negligent. He further contends that this failure prevented 

him from being able to enforce the settlement agreement’s liquidated damages clause. 

Again, Husch Blackwell disputes Nail’s allegations of negligence. But assuming 

that Nail offered sufficient evidence that Husch Blackwell negligently drafted the 

settlement agreement, he must still show that, but for its negligence, he would have had a 

liquidated damages claim against Mueller. To do this, he must prove that Mueller would 

have agreed to include the necessary provisions in the settlement agreement and then 

later would have breached them. See Bryant v. Bryan Cave; 400 S.W.3d 325, 331 (Mo. 

App. 2013); Steward v. Goetz, 945 S.W.2d 520, 532-33 (Mo. App. 1997); Lange v. 

Marshall, 622 S.W.2d 237, 239 (Mo. App. 1981). Assuming Husch Blackwell had 

included language in the settlement agreement requiring Mueller to provide the transfer 

documents required by the London Stock Exchange, Mueller would have had to agree to 

these provisions. Mueller would also have had to agree to provide those documents at the 

same time as the transfer notice—immediately upon the expiration of the lock-up 

period—and not insist on a different time requirement. Moreover, Mueller would have 

had to agree to make his non-compliance with these provisions subject to the liquidated 

damages clause. And then, after he had agreed to all of these things, Mueller would then 

have had to ignore his obligations under the settlement agreement and subject himself to 

millions of dollars in liquidated damages. This is all pure speculation. 

 Nail has not offered any evidence that Mueller would have agreed to any of these 

provisions or that he then would have breached them. Most importantly, Nail’s 

hypothesis that Mueller ultimately would have breached the settlement agreement is 

15 
belied by the undisputed facts of the case. In reality, Mueller scrupulously complied with 

his obligations under the settlement agreement, and he promptly provided the additional 

documents required by the London Stock Exchange upon Nail’s request. There is 

nothing in the record to suggest that he would not have done so if the settlement 

agreement had been drafted as Nail argues it should have been—especially when his 

failure would have subjected him to millions of dollars in liquidated damages. 

 Nail argues alternatively that Husch Blackwell’s negligence in drafting the 

settlement agreement diminished the value of his stock options. In his view, the 

settlement agreement’s failure to require Mueller to place all of the documents necessary 

to transfer the stock into escrow subjected him to the risk of delay any time he exercised 

his options. He still must prove, however, that but for Husch Blackwell’s negligent 

drafting the result would have been more favorable. As with his first argument, Nail 

must prove that Mueller would have agreed to the relevant provisions, and he has offered 

no evidence on this point. He must also prove that he would have realized a greater profit 

on his stock options if these provisions had become part of the settlement agreement. 

Steward, 945 S.W.2d at 532-33. To the contrary, Nail stipulated that no damages were 

caused when his first exercise was delayed pending Mueller’s delivery of the stock 

transfer form, and he concedes that he eventually exercised nearly all of his stock options 

and realized profits in excess of $600,000. He offered no evidence that, but for the risk 

16 
17 

 

of delay presented by Husch Blackwell’s alleged negligence, he would have exercised 

more of his stock options or realized more profit.10

 Nail failed to prove that, but for Husch Blackwell’s allegedly negligent drafting, 

he would have obtained a more favorable outcome. Accordingly, the trial court did not 

err in entering summary judgment for Husch Blackwell on this claim. 

Conclusion 

 The trial court’s judgment is affirmed. 

 _____________________________ 

 Mary R. Russell, Chief Justice 

Fischer, Stith, Draper, Wilson 

and Teitelman, JJ., concur. 

Breckenridge, J., not participating. 

10 Nail argues that, if Husch Blackwell’s alleged negligent drafting diminished the value of his 

stock options, the measure of damages should be the amount of the liquidated damages clause 

because that amount was a reasonable prediction of the harm caused by interference with his 

options. This argument is out of step with the established measure of damages in legal 

malpractice claims, which is the amount the client would have received but for the attorney’s 

negligence. Thiel v. Miller, 164 S.W.3d 76, 82 (Mo. App. 2005). Further, he must still 

demonstrate that he would have been better off if Husch Blackwell had drafted the settlement 

agreement as he argues it should have. Donahue, 900 S.W.2d at 626. Nail complains that the 

settlement agreement created a risk of delay that diminished the value of his stock options; he 

must prove, therefore, that, but for this risk, he would have realized greater profit. His claim 

fails because he did not make the required showing.